tert-Butyl N-[(11-exo-benzyl­oxy­carbonyl-8-oxopenta­cyclo­[5.4.0.02,6.03,10.05,9]undecane-11-endo-yloxy)carbon­yl­methyl]carbamate

Karpoormath, R.; Govender, T.; Govender, P.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536810036627

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2607-o2608

doi:10.1107/S1600536810036627

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tert-Butyl N-[(11-exo-benzyloxycarbonyl-8-oxopentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-11-endo-yloxy)carbonylmethyl]carbamate

Rajshekhar Karpoormath,^a Thavendran Govender,^b Patrick Govender,^c Hendrik G. Kruger ^a and Glenn E. M. Maguire ^a ^*

^aSchool of Chemistry, University of KwaZulu–Natal, Durban 4000, South Africa, ^bSchool of Pharmacy and Pharmacology, University of KwaZulu–Natal, Durban, South Africa, and ^cDepartment of Biochemistry, University of KwaZulu–Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 8 September 2010; accepted 13 September 2010; online 25 September 2010)

The structure of the title compound, C₂₆H₂₉NO₇, at 173 K has an intermolecular N—H⋯O hydrogen bond. This is one of the few examples where a mono-ketone pentacycloundecane (PCU) molecule exibits hydrogen bonding in the solid state. The dihedral angles of the amide and ester groups are normal and unaffected by the cage structure. A longer than normal C—C bond [1.571 (4) Å] was found within the cage structure.

Related literature

For examples of cage structures with C—C bonds lengths that differ from normal, see: Marchand (1989 ); Kruger et al. (2006 ). For examples of crystal structures of mono-ketone PCU molecules bearing heteroatoms, see: Watson et al. (2000 ); Flippen-Anderson et al. (1991 ); Liu et al. (2001 ). For the synthesis of the precursors, see: Martins et al. (1993 ).

Experimental

Crystal data

C₂₆H₂₉NO₇
M_r = 467.50
Monoclinic, C c
a = 9.7260 (2) Å
b = 27.5398 (7) Å
c = 9.3500 (2) Å
β = 107.679 (1)°
V = 2386.14 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 173 K
0.24 × 0.22 × 0.19 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.694, T_max = 0.753
8919 measured reflections
3948 independent reflections
3802 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.100
S = 1.07
3948 reflections
311 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1760 Friedel pairs
Flack parameter: 0.00 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.96 (1)	1.99 (2)	2.882 (2)	154 (2)
Symmetry code: (i) $[x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036627/om2360sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036627/om2360Isup2.hkl

checkCIF report

Comment top

Pentacycloundecane (PCU) derivatives have been reported in a wide range of chemical fields (Marchand, 1989). We have reported the structures of a number of PCU derivatives including a mono-ketone ethylene acetal (Kruger et al., 2006). Previous examples of this group of mono-ketone molecules have included crown ether (Watson et al., 2000), nitro derivatives (Flippen-Anderson et al., 1991) and benzylic amines (Liu et al., 2001). The title compound (Fig. 1) is a rare example of a monoketone PCU with an intermolecular hydrogen bonding interaction and also features a PCU cage ester bond (Watson et al., 2000). The intermolecular N1—H···O1 bond interaction (2.882 Å) holds the structure in interdigitated rows. The intermolecular distances between the ring centroids in the a axis direction of 5.641–7.710 Å, suggests that there is no π-stacking interaction between parallel molecules (Fig. 2).

Related literature top

For examples of cage structures with C—C bonds lengths that differ from normal, see: Marchand (1989); Kruger et al. (2006). For examples of crystal structures of mono-ketone PCU molecules bearing heteroatoms, see: Watson et al. (2000); Flippen-Anderson et al. (1991); Liu et al. (2001). For the synthesis of the precursors, see: Martins et al. (1993).

Experimental top

5-Hydroxy-4-oxahexacyclo[5.4.0.0^2,6.0^3,10.0^5,9]dodecane-3-carboxybenzylester (1.0 g, 3.2 mmol) (Martins et al., 1993) was dissolved in dichloromethane (15 ml) and reacted, under stirring, with BOC-glycine (1.2 g, 6.4 mmol), diisopropylcarbodiimide (0.7 ml, 6.4 mmol), and DMAP (0.04 g, 0.32 mmol) overnight at ambient temperature. The resulting solution was washed with HCl (0.1 N) and water and then extracted with ethyl acetate. The organic layer was dried Na₂SO₄, filtered, and concentrated under vacuum. The product was isolated by silica flash column chromatography (15% ethyl acetate in hexane) to give the product, (0.6 g, 60% yield). Crystallization of the product was carried out by dissolving the product in 5 ml a solvent mixture of ethyl acetate and hexane (1:5) at 22 °C.

¹H NMR (CDCl₃, 400 MHz) δ p.p.m.: 1.42 (9.0H, s), 1.53 (1.0H, d, J=11.17 Hz), 1.72 (1.0H, s), 1.84 (1.0H, d, J=11.25 Hz), 2.49 (2.0H, m, J=2.21 Hz), 2.58 (1.0H, d, J=4.04 Hz), 2.63 (1.0H, d, J=3.72 Hz), 2.81 (1.0H, m, J=5.01 Hz), 2.99 (1.0H, q, J=3.19 Hz), 3.05 (1.0H, d, J=6.92 Hz), 3.59 (1.0H, t, J=7.06 Hz), 3.83 (2.0H, m, J=9.47 Hz), 4.85 (1.0H, s), 5.12 (2.0H, d, J=5.32 Hz), 7.28–7.34 (5.0H, m, J=4.99 Hz).

¹³C NMR (CDCl₃, 100 MHz) δ p.p.m.: 28.32 (s), 36.25 (s), 38.15 (s), 40.54 (s), 41.50 (s), 41.93 (s), 42.35 (s), 43.15 (s), 43.92 (s), 50.17 (s), 54.33 (s), 67.42 (s), 79.87 (s), 84.66 (s), 128.43 (t, J=20.32 Hz), 135.10 (s), 155.41 (s), 169.43 (d, J=23.32 Hz), 214.23 (s)

IR (neat) V_max cm^-1:3373.08, 2973.02, 1710.33, 1518.09, 1366.27, 1268.62, 1150.16, 1116.67, 1061.14, 743.63, 697.37.

HR ESI m/z: calcd for C₂₆H₂₉NO₇ [M+H]⁺: 490.1826 found 490.1823.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the numbering scheme. All non-hydrogen atoms are shown as ellipsoids with probability level of 30%.
	Fig. 2. Partial projection viewed along [100]. All hydrogen atoms except the hydrogen H1N on N1 are omitted. The hydrogen bonds are shown as dotted lines.

tert-Butyl N-[(11-exo-benzyloxycarbonyl-8- oxopentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-11-endo- yloxy)carbonylmethyl]carbamate top

Crystal data top

C₂₆H₂₉NO₇	F(000) = 992
M_r = 467.50	D_x = 1.301 Mg m⁻³
Monoclinic, Cc	Cu Kα radiation, λ = 1.54178 Å
a = 9.7260 (2) Å	Cell parameters from 8919 reflections
b = 27.5398 (7) Å	θ = 5.9–68.1°
c = 9.3500 (2) Å	µ = 0.78 mm⁻¹
β = 107.679 (1)°	T = 173 K
V = 2386.14 (9) Å³	Block, colourless
Z = 4	0.24 × 0.22 × 0.19 mm

Data collection top

Bruker Kappa DUO APEXII diffractometer	3948 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
0.5° ϕ scans and ω scans	θ_max = 68.1°, θ_min = 5.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→11
T_min = 0.694, T_max = 0.753	k = −30→32
8919 measured reflections	l = −11→10

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0509P)² + 1.0452P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3948 reflections	Δρ_max = 0.21 e Å⁻³
311 parameters	Δρ_min = −0.18 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1760 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (18)

Crystal data top

C₂₆H₂₉NO₇	V = 2386.14 (9) Å³
M_r = 467.50	Z = 4
Monoclinic, Cc	Cu Kα radiation
a = 9.7260 (2) Å	µ = 0.78 mm⁻¹
b = 27.5398 (7) Å	T = 173 K
c = 9.3500 (2) Å	0.24 × 0.22 × 0.19 mm
β = 107.679 (1)°

Data collection top

Bruker Kappa DUO APEXII diffractometer	3948 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3802 reflections with I > 2σ(I)
T_min = 0.694, T_max = 0.753	R_int = 0.024
8919 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	Δρ_max = 0.21 e Å⁻³
S = 1.07	Δρ_min = −0.18 e Å⁻³
3948 reflections	Absolute structure: Flack (1983), 1760 Friedel pairs
311 parameters	Absolute structure parameter: 0.00 (18)
3 restraints

Special details top

Experimental. Half sphere of data collected using SAINT strategy (Bruker, 2006). Crystal to detector distance = 50 mm; combination of ϕ and ω scans of 0.5°, 40 s per °, 2 iterations.

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	0.65693 (19)	1.00052 (6)	0.9771 (2)	0.0521 (4)
O2	0.76432 (15)	0.90113 (5)	0.91549 (15)	0.0358 (3)
O3	0.7061 (2)	0.87716 (7)	0.67501 (18)	0.0564 (5)
O4	1.1178 (2)	0.90102 (8)	0.6733 (2)	0.0619 (5)
O5	1.00520 (16)	0.93227 (6)	0.44177 (16)	0.0452 (4)
O6	0.5895 (2)	0.78765 (6)	0.8670 (3)	0.0661 (5)
O7	0.8234 (2)	0.80702 (6)	0.9488 (3)	0.0642 (5)
N1	0.9078 (2)	0.94186 (8)	0.6227 (2)	0.0454 (4)
H1N	0.836 (2)	0.9596 (8)	0.549 (2)	0.049 (7)*
C1	0.4838 (3)	0.88257 (10)	1.2375 (3)	0.0584 (6)
H1A	0.5564	0.8807	1.3379	0.070*
H1B	0.3871	0.8739	1.2442	0.070*
C2	0.4852 (3)	0.93103 (9)	1.1615 (3)	0.0504 (6)
H2	0.4599	0.9597	1.2140	0.060*
C3	0.6376 (3)	0.93282 (8)	1.1385 (2)	0.0423 (5)
H3	0.7140	0.9474	1.2248	0.051*
C4	0.6031 (2)	0.96254 (8)	0.9971 (2)	0.0411 (5)
C5	0.4713 (3)	0.93899 (8)	0.8917 (3)	0.0464 (5)
H5	0.4163	0.9584	0.8021	0.056*
C6	0.3875 (3)	0.92269 (9)	1.0015 (3)	0.0507 (6)
H6	0.2846	0.9332	0.9777	0.061*
C7	0.5258 (3)	0.85303 (8)	1.1207 (3)	0.0503 (6)
H7	0.5335	0.8173	1.1397	0.060*
C8	0.6645 (2)	0.87760 (8)	1.1087 (2)	0.0385 (4)
H8	0.7545	0.8642	1.1809	0.046*
C9	0.6564 (2)	0.86978 (7)	0.9442 (2)	0.0375 (4)
C10	0.5005 (3)	0.88424 (8)	0.8639 (3)	0.0445 (5)
H10	0.4605	0.8727	0.7579	0.053*
C11	0.4164 (3)	0.86818 (9)	0.9720 (3)	0.0503 (6)
H11	0.3305	0.8468	0.9305	0.060*
C12	0.7770 (2)	0.90133 (7)	0.7760 (2)	0.0377 (4)
C13	0.8940 (3)	0.93654 (8)	0.7718 (2)	0.0422 (5)
H13A	0.8725	0.9686	0.8077	0.051*
H13B	0.9870	0.9252	0.8409	0.051*
C14	1.0199 (2)	0.92285 (8)	0.5870 (2)	0.0394 (5)
C15	1.1196 (2)	0.91702 (8)	0.3776 (2)	0.0402 (5)
C16	1.2606 (3)	0.94073 (13)	0.4606 (3)	0.0650 (8)
H16A	1.2484	0.9761	0.4575	0.097*
H16B	1.3340	0.9318	0.4131	0.097*
H16C	1.2911	0.9297	0.5652	0.097*
C17	1.0661 (3)	0.93591 (14)	0.2193 (3)	0.0681 (8)
H17A	1.0606	0.9714	0.2210	0.102*
H17B	0.9701	0.9225	0.1694	0.102*
H17C	1.1328	0.9260	0.1644	0.102*
C18	1.1285 (4)	0.86241 (11)	0.3777 (4)	0.0756 (9)
H18A	1.0340	0.8489	0.3228	0.113*
H18B	1.1574	0.8505	0.4814	0.113*
H18C	1.2000	0.8523	0.3290	0.113*
C19	0.6842 (3)	0.81669 (8)	0.9137 (3)	0.0483 (5)
C20	0.8571 (4)	0.75648 (10)	0.9237 (6)	0.1008 (15)
H20A	0.7839	0.7436	0.8334	0.121*
H20B	0.8553	0.7364	1.0109	0.121*
C21	1.0032 (3)	0.75425 (8)	0.9029 (3)	0.0489 (6)
C22	1.0989 (4)	0.71945 (11)	0.9751 (3)	0.0657 (8)
H22	1.0766	0.6993	1.0474	0.079*
C23	1.2270 (3)	0.71335 (13)	0.9445 (4)	0.0726 (8)
H23	1.2910	0.6882	0.9931	0.087*
C24	1.2633 (3)	0.74254 (11)	0.8465 (5)	0.0752 (9)
H24	1.3543	0.7389	0.8298	0.090*
C25	1.1698 (4)	0.77737 (10)	0.7713 (3)	0.0625 (7)
H25	1.1948	0.7976	0.7008	0.075*
C26	1.0372 (3)	0.78318 (9)	0.7980 (3)	0.0537 (6)
H26	0.9707	0.8069	0.7442	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0568 (10)	0.0371 (8)	0.0610 (10)	−0.0109 (7)	0.0157 (8)	−0.0025 (7)
O2	0.0419 (8)	0.0373 (7)	0.0348 (7)	−0.0062 (6)	0.0216 (6)	−0.0046 (6)
O3	0.0766 (12)	0.0561 (10)	0.0430 (9)	−0.0195 (9)	0.0279 (8)	−0.0168 (7)
O4	0.0599 (11)	0.0840 (13)	0.0476 (9)	0.0323 (9)	0.0251 (8)	0.0226 (9)
O5	0.0425 (8)	0.0613 (10)	0.0387 (8)	0.0141 (7)	0.0227 (7)	0.0115 (7)
O6	0.0722 (12)	0.0430 (10)	0.1014 (15)	−0.0175 (9)	0.0537 (12)	−0.0225 (9)
O7	0.0624 (11)	0.0325 (8)	0.1147 (15)	0.0020 (8)	0.0524 (11)	0.0000 (9)
N1	0.0460 (11)	0.0583 (11)	0.0396 (10)	0.0134 (9)	0.0244 (9)	0.0137 (8)
C1	0.0604 (16)	0.0588 (14)	0.0715 (16)	0.0052 (12)	0.0429 (14)	0.0033 (13)
C2	0.0528 (14)	0.0471 (13)	0.0614 (15)	−0.0017 (10)	0.0326 (12)	−0.0095 (11)
C3	0.0477 (12)	0.0437 (12)	0.0398 (11)	−0.0039 (9)	0.0200 (9)	−0.0083 (9)
C4	0.0410 (11)	0.0354 (11)	0.0498 (12)	−0.0035 (8)	0.0182 (10)	−0.0077 (9)
C5	0.0442 (12)	0.0386 (11)	0.0528 (13)	−0.0024 (9)	0.0095 (10)	−0.0039 (10)
C6	0.0374 (12)	0.0401 (12)	0.0777 (17)	0.0016 (9)	0.0219 (11)	−0.0018 (11)
C7	0.0553 (14)	0.0384 (11)	0.0744 (16)	0.0039 (10)	0.0455 (13)	0.0086 (10)
C8	0.0437 (11)	0.0375 (11)	0.0416 (11)	0.0001 (9)	0.0239 (9)	0.0002 (8)
C9	0.0419 (11)	0.0343 (10)	0.0436 (11)	−0.0072 (8)	0.0239 (9)	−0.0063 (8)
C10	0.0442 (12)	0.0392 (12)	0.0503 (12)	−0.0066 (9)	0.0148 (9)	−0.0098 (9)
C11	0.0432 (12)	0.0412 (12)	0.0724 (15)	−0.0093 (9)	0.0267 (11)	−0.0121 (11)
C12	0.0482 (12)	0.0341 (10)	0.0356 (10)	0.0030 (9)	0.0201 (9)	−0.0043 (8)
C13	0.0501 (12)	0.0475 (12)	0.0369 (11)	−0.0020 (9)	0.0248 (10)	−0.0016 (9)
C14	0.0435 (11)	0.0412 (11)	0.0381 (11)	0.0039 (9)	0.0193 (9)	0.0060 (9)
C15	0.0399 (11)	0.0477 (12)	0.0395 (11)	0.0057 (9)	0.0219 (9)	0.0026 (9)
C16	0.0528 (15)	0.090 (2)	0.0597 (16)	−0.0151 (14)	0.0291 (13)	−0.0203 (14)
C17	0.0548 (16)	0.113 (3)	0.0451 (13)	0.0158 (15)	0.0281 (12)	0.0128 (14)
C18	0.103 (2)	0.0515 (15)	0.101 (2)	0.0018 (15)	0.074 (2)	−0.0042 (15)
C19	0.0599 (14)	0.0373 (12)	0.0645 (14)	−0.0069 (10)	0.0441 (12)	−0.0068 (10)
C20	0.105 (3)	0.0329 (14)	0.207 (5)	0.0056 (14)	0.112 (3)	0.0042 (19)
C21	0.0586 (14)	0.0324 (10)	0.0659 (15)	0.0048 (10)	0.0341 (12)	0.0034 (10)
C22	0.090 (2)	0.0604 (16)	0.0514 (14)	0.0184 (15)	0.0279 (14)	0.0185 (12)
C23	0.0599 (17)	0.073 (2)	0.077 (2)	0.0147 (14)	0.0076 (15)	0.0090 (15)
C24	0.0459 (13)	0.0561 (17)	0.128 (3)	−0.0112 (13)	0.0331 (16)	−0.0265 (18)
C25	0.089 (2)	0.0453 (13)	0.0697 (17)	−0.0167 (13)	0.0478 (16)	−0.0030 (12)
C26	0.0608 (15)	0.0406 (12)	0.0575 (14)	0.0066 (10)	0.0144 (12)	0.0122 (10)

Geometric parameters (Å, º) top

O1—C4	1.210 (3)	C9—C10	1.527 (3)
O2—C12	1.347 (2)	C9—C19	1.529 (3)
O2—C9	1.445 (2)	C10—C11	1.546 (3)
O3—C12	1.189 (3)	C10—H10	1.0000
O4—C14	1.205 (3)	C11—H11	1.0000
O5—C14	1.347 (3)	C12—C13	1.505 (3)
O5—C15	1.476 (2)	C13—H13A	0.9900
O6—C19	1.198 (3)	C13—H13B	0.9900
O7—C19	1.320 (3)	C15—C16	1.504 (4)
O7—C20	1.465 (3)	C15—C17	1.505 (3)
N1—C14	1.340 (3)	C15—C18	1.506 (4)
N1—C13	1.448 (3)	C16—H16A	0.9800
N1—H1N	0.955 (10)	C16—H16B	0.9800
C1—C7	1.514 (4)	C16—H16C	0.9800
C1—C2	1.514 (4)	C17—H17A	0.9800
C1—H1A	0.9900	C17—H17B	0.9800
C1—H1B	0.9900	C17—H17C	0.9800
C2—C6	1.526 (4)	C18—H18A	0.9800
C2—C3	1.562 (3)	C18—H18B	0.9800
C2—H2	1.0000	C18—H18C	0.9800
C3—C4	1.504 (3)	C20—C21	1.494 (4)
C3—C8	1.582 (3)	C20—H20A	0.9900
C3—H3	1.0000	C20—H20B	0.9900
C4—C5	1.506 (3)	C21—C22	1.364 (4)
C5—C6	1.559 (4)	C21—C26	1.379 (3)
C5—C10	1.570 (3)	C22—C23	1.371 (5)
C5—H5	1.0000	C22—H22	0.9500
C6—C11	1.567 (3)	C23—C24	1.343 (5)
C6—H6	1.0000	C23—H23	0.9500
C7—C11	1.530 (4)	C24—C25	1.361 (5)
C7—C8	1.544 (3)	C24—H24	0.9500
C7—H7	1.0000	C25—C26	1.395 (4)
C8—C9	1.531 (3)	C25—H25	0.9500
C8—H8	1.0000	C26—H26	0.9500

C12—O2—C9	117.85 (16)	C7—C11—H11	117.4
C14—O5—C15	119.49 (17)	C10—C11—H11	117.4
C19—O7—C20	114.5 (2)	C6—C11—H11	117.4
C14—N1—C13	121.39 (19)	O3—C12—O2	124.4 (2)
C14—N1—H1N	119.6 (17)	O3—C12—C13	126.89 (19)
C13—N1—H1N	119.0 (17)	O2—C12—C13	108.69 (17)
C7—C1—C2	95.3 (2)	N1—C13—C12	112.50 (19)
C7—C1—H1A	112.7	N1—C13—H13A	109.1
C2—C1—H1A	112.7	C12—C13—H13A	109.1
C7—C1—H1B	112.7	N1—C13—H13B	109.1
C2—C1—H1B	112.7	C12—C13—H13B	109.1
H1A—C1—H1B	110.2	H13A—C13—H13B	107.8
C1—C2—C6	103.6 (2)	O4—C14—N1	124.4 (2)
C1—C2—C3	103.7 (2)	O4—C14—O5	126.3 (2)
C6—C2—C3	101.79 (18)	N1—C14—O5	109.31 (19)
C1—C2—H2	115.3	O5—C15—C16	110.40 (19)
C6—C2—H2	115.3	O5—C15—C17	102.88 (18)
C3—C2—H2	115.3	C16—C15—C17	110.2 (2)
C4—C3—C2	99.81 (19)	O5—C15—C18	109.52 (19)
C4—C3—C8	111.90 (17)	C16—C15—C18	113.0 (2)
C2—C3—C8	102.04 (17)	C17—C15—C18	110.4 (2)
C4—C3—H3	113.9	C15—C16—H16A	109.5
C2—C3—H3	113.9	C15—C16—H16B	109.5
C8—C3—H3	113.9	H16A—C16—H16B	109.5
O1—C4—C3	128.0 (2)	C15—C16—H16C	109.5
O1—C4—C5	126.4 (2)	H16A—C16—H16C	109.5
C3—C4—C5	105.04 (19)	H16B—C16—H16C	109.5
C4—C5—C6	101.77 (19)	C15—C17—H17A	109.5
C4—C5—C10	111.17 (19)	C15—C17—H17B	109.5
C6—C5—C10	89.40 (18)	H17A—C17—H17B	109.5
C4—C5—H5	116.8	C15—C17—H17C	109.5
C6—C5—H5	116.8	H17A—C17—H17C	109.5
C10—C5—H5	116.8	H17B—C17—H17C	109.5
C2—C6—C5	107.93 (19)	C15—C18—H18A	109.5
C2—C6—C11	103.0 (2)	C15—C18—H18B	109.5
C5—C6—C11	90.14 (18)	H18A—C18—H18B	109.5
C2—C6—H6	117.3	C15—C18—H18C	109.5
C5—C6—H6	117.3	H18A—C18—H18C	109.5
C11—C6—H6	117.3	H18B—C18—H18C	109.5
C1—C7—C11	104.1 (2)	O6—C19—O7	125.0 (2)
C1—C7—C8	104.5 (2)	O6—C19—C9	123.1 (2)
C11—C7—C8	101.31 (18)	O7—C19—C9	111.9 (2)
C1—C7—H7	115.1	O7—C20—C21	109.1 (2)
C11—C7—H7	115.1	O7—C20—H20A	109.9
C8—C7—H7	115.1	C21—C20—H20A	109.9
C9—C8—C7	103.44 (18)	O7—C20—H20B	109.9
C9—C8—C3	110.57 (17)	C21—C20—H20B	109.9
C7—C8—C3	102.31 (17)	H20A—C20—H20B	108.3
C9—C8—H8	113.2	C22—C21—C26	118.9 (3)
C7—C8—H8	113.2	C22—C21—C20	119.8 (3)
C3—C8—H8	113.2	C26—C21—C20	120.8 (3)
O2—C9—C10	114.94 (17)	C21—C22—C23	120.6 (3)
O2—C9—C19	110.94 (17)	C21—C22—H22	119.7
C10—C9—C19	111.30 (18)	C23—C22—H22	119.7
O2—C9—C8	106.48 (16)	C24—C23—C22	120.8 (3)
C10—C9—C8	101.39 (17)	C24—C23—H23	119.6
C19—C9—C8	111.31 (18)	C22—C23—H23	119.6
C9—C10—C11	104.35 (19)	C23—C24—C25	120.1 (3)
C9—C10—C5	111.82 (18)	C23—C24—H24	119.9
C11—C10—C5	90.48 (18)	C25—C24—H24	119.9
C9—C10—H10	115.7	C24—C25—C26	119.8 (3)
C11—C10—H10	115.7	C24—C25—H25	120.1
C5—C10—H10	115.7	C26—C25—H25	120.1
C7—C11—C10	108.19 (19)	C21—C26—C25	119.7 (2)
C7—C11—C6	102.3 (2)	C21—C26—H26	120.2
C10—C11—C6	89.98 (18)	C25—C26—H26	120.2

C7—C1—C2—C6	52.8 (2)	C4—C5—C10—C9	−2.9 (3)
C7—C1—C2—C3	−53.2 (2)	C6—C5—C10—C9	−105.3 (2)
C1—C2—C3—C4	149.0 (2)	C4—C5—C10—C11	102.8 (2)
C6—C2—C3—C4	41.6 (2)	C6—C5—C10—C11	0.38 (19)
C1—C2—C3—C8	33.9 (2)	C1—C7—C11—C10	127.0 (2)
C6—C2—C3—C8	−73.4 (2)	C8—C7—C11—C10	18.7 (2)
C2—C3—C4—O1	122.5 (3)	C1—C7—C11—C6	32.9 (2)
C8—C3—C4—O1	−130.2 (2)	C8—C7—C11—C6	−75.4 (2)
C2—C3—C4—C5	−49.2 (2)	C9—C10—C11—C7	9.3 (2)
C8—C3—C4—C5	58.2 (2)	C5—C10—C11—C7	−103.4 (2)
O1—C4—C5—C6	−136.1 (2)	C9—C10—C11—C6	112.32 (18)
C3—C4—C5—C6	35.7 (2)	C5—C10—C11—C6	−0.38 (18)
O1—C4—C5—C10	129.9 (3)	C2—C6—C11—C7	0.6 (2)
C3—C4—C5—C10	−58.2 (2)	C5—C6—C11—C7	109.02 (19)
C1—C2—C6—C5	−128.2 (2)	C2—C6—C11—C10	−108.1 (2)
C3—C2—C6—C5	−20.8 (2)	C5—C6—C11—C10	0.38 (19)
C1—C2—C6—C11	−33.8 (2)	C9—O2—C12—O3	−0.6 (3)
C3—C2—C6—C11	73.7 (2)	C9—O2—C12—C13	179.57 (17)
C4—C5—C6—C2	−8.2 (2)	C14—N1—C13—C12	−107.3 (3)
C10—C5—C6—C2	103.3 (2)	O3—C12—C13—N1	4.5 (3)
C4—C5—C6—C11	−111.89 (19)	O2—C12—C13—N1	−175.63 (18)
C10—C5—C6—C11	−0.38 (18)	C13—N1—C14—O4	−1.3 (4)
C2—C1—C7—C11	−52.6 (2)	C13—N1—C14—O5	178.9 (2)
C2—C1—C7—C8	53.3 (2)	C15—O5—C14—O4	−2.7 (4)
C1—C7—C8—C9	−148.1 (2)	C15—O5—C14—N1	176.98 (19)
C11—C7—C8—C9	−40.1 (2)	C14—O5—C15—C16	−59.9 (3)
C1—C7—C8—C3	−33.1 (2)	C14—O5—C15—C17	−177.5 (2)
C11—C7—C8—C3	74.8 (2)	C14—O5—C15—C18	65.1 (3)
C4—C3—C8—C9	3.2 (2)	C20—O7—C19—O6	1.1 (4)
C2—C3—C8—C9	109.08 (19)	C20—O7—C19—C9	179.3 (3)
C4—C3—C8—C7	−106.4 (2)	O2—C9—C19—O6	−147.2 (2)
C2—C3—C8—C7	−0.6 (2)	C10—C9—C19—O6	−17.9 (3)
C12—O2—C9—C10	−67.7 (2)	C8—C9—C19—O6	94.5 (3)
C12—O2—C9—C19	59.7 (2)	O2—C9—C19—O7	34.5 (3)
C12—O2—C9—C8	−179.06 (17)	C10—C9—C19—O7	163.9 (2)
C7—C8—C9—O2	167.11 (17)	C8—C9—C19—O7	−83.8 (2)
C3—C8—C9—O2	58.2 (2)	C19—O7—C20—C21	155.9 (3)
C7—C8—C9—C10	46.57 (19)	O7—C20—C21—C22	134.8 (3)
C3—C8—C9—C10	−62.3 (2)	O7—C20—C21—C26	−52.9 (5)
C7—C8—C9—C19	−71.9 (2)	C26—C21—C22—C23	0.2 (5)
C3—C8—C9—C19	179.23 (18)	C20—C21—C22—C23	172.6 (3)
O2—C9—C10—C11	−148.11 (17)	C21—C22—C23—C24	2.3 (5)
C19—C9—C10—C11	84.7 (2)	C22—C23—C24—C25	−2.9 (5)
C8—C9—C10—C11	−33.7 (2)	C23—C24—C25—C26	1.1 (5)
O2—C9—C10—C5	−51.7 (3)	C22—C21—C26—C25	−2.0 (4)
C19—C9—C10—C5	−178.88 (19)	C20—C21—C26—C25	−174.3 (3)
C8—C9—C10—C5	62.7 (2)	C24—C25—C26—C21	1.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.96 (1)	1.99 (2)	2.882 (2)	154 (2)

Symmetry code: (i) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₉NO₇
M_r	467.50
Crystal system, space group	Monoclinic, Cc
Temperature (K)	173
a, b, c (Å)	9.7260 (2), 27.5398 (7), 9.3500 (2)
β (°)	107.679 (1)
V (Å³)	2386.14 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.24 × 0.22 × 0.19

Data collection
Diffractometer	Bruker Kappa DUO APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.694, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	8919, 3948, 3802
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.100, 1.07
No. of reflections	3948
No. of parameters	311
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18
Absolute structure	Flack (1983), 1760 Friedel pairs
Absolute structure parameter	0.00 (18)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.955 (10)	1.993 (15)	2.882 (2)	154 (2)

Symmetry code: (i) x, −y+2, z−1/2.

Acknowledgements

The authors would like to thank Dr Hong Su (University of Capetown) for the data collection and structure refinement.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2006). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flippen-Anderson, J. L., George, C., Gilardi, R., Zajac, W. W., Walters, T. R., Marchand, A., Dave, P. R. & Arney, B. E. (1991). Acta Cryst. C47, 813–817. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268–o270. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, X., Kassiou, M., Christie, M. J. & Hambley, T. W. (2001). Aust. J. Chem. 54, 31–35. Web of Science CSD CrossRef CAS Google Scholar
Marchand, A. P. (1989). Chem. Rev. 89, 1011–1033. CrossRef CAS Web of Science Google Scholar
Martins, F. J. C., Viljoen, A. M., Kruger, H. G. & Joubert, J. A. (1993). Tetrahedron, 49, 9573–9580. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watson, W. H., Bodige, S. G., Marchand, A. P. & Chong, H.-S. (2000). Struct. Chem. 11, 257–260. Web of Science CSD CrossRef CAS Google Scholar

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Volume 66| Part 10| October 2010| Pages o2607-o2608

doi:10.1107/S1600536810036627

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

tert-Butyl N-[(11-exo-benzyl­­oxy­carbonyl-8-oxo­penta­cyclo­[5.4.0.02,6.03,10.05,9]undecane-11-endo-yl­oxy)carbon­yl­methyl]carbamate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

tert-Butyl N-[(11-exo-benzyloxycarbonyl-8-oxopentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-11-endo-yloxy)carbonylmethyl]carbamate