(1S,4S,5S,8R)-8-Nitro-oxy-2,6-dioxa-bicyclo-[3.3.0]octan-4-yl 3,4,5-triacetoxy-benzoate.

In the title compound, C(19)H(19)NO(13), one of the two fused furan-ose rings adopts an envelope conformation whereas the other displays a twisted conformation. The crystal structure is stabilized by inter-molecular C-H⋯π inter-actions between a methine H atom and the triacetoxy-phenyl ring of an adjacent mol-ecule, and by weak non-classical inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Velazquez et al. (2007 ▶), Calmès et al.(2003 ▶). For related structures, see: Ezhilmuthu et al. (2008 ▶). For the bioactivity of the title compound, see: Rigas & Williams (2008 ▶); Carini et al. (2002 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶); Rao et al. (1981 ▶). For the determination of the absolute structure, see: van Koningsveld et al. (1984 ▶); Brown et al. (2000 ▶).

Experimental

Crystal data

C19H19NO13

M = 469.35

Monoclinic,

a = 10.8053 (19) Å

b = 6.5941 (12) Å

c = 16.075 (3) Å

β = 108.243 (3)°

V = 1087.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.31 × 0.25 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.962, T max = 0.983

5474 measured reflections

2112 independent reflections

1394 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.02

2112 reflections

301 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042524/dn2497sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042524/dn2497Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H19NO13	F(000) = 488
Mr = 469.35	Dx = 1.433 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1117 reflections
a = 10.8053 (19) Å	θ = 2.7–19.9°
b = 6.5941 (12) Å	µ = 0.12 mm−1
c = 16.075 (3) Å	T = 296 K
β = 108.243 (3)°	Block, colorless
V = 1087.8 (3) Å3	0.31 × 0.25 × 0.14 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2112 independent reflections
Radiation source: fine-focus sealed tube	1394 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.962, Tmax = 0.983	k = −7→7
5474 measured reflections	l = 0→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0523P)2] where P = (Fo2 + 2Fc2)/3
2112 reflections	(Δ/σ)max < 0.001
301 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
N1	−0.0658 (8)	0.548 (4)	0.4472 (4)	0.1120 (17)
O2	−0.0166 (3)	0.369 (4)	0.28660 (18)	0.0708 (8)
O6	0.0245 (3)	0.779 (4)	0.21440 (17)	0.0650 (8)
O8	0.5258 (2)	−0.138 (4)	0.32531 (17)	0.0659 (8)
O9	0.3795 (4)	−0.169 (4)	0.39702 (18)	0.0954 (12)
O10	0.5277 (3)	−0.439 (4)	0.20426 (18)	0.0688 (8)
O11	0.4726 (3)	−0.581 (4)	0.3144 (2)	0.0781 (9)
O12	0.3201 (3)	−0.487 (4)	0.05899 (17)	0.0737 (8)
O13	0.3616 (5)	−0.318 (4)	−0.0486 (2)	0.1167 (14)
O41	0.1465 (2)	0.293 (4)	0.17708 (15)	0.0585 (7)
O42	0.0434 (3)	0.151 (4)	0.04764 (18)	0.0826 (10)
O81	−0.0735 (3)	0.671 (4)	0.37604 (19)	0.0816 (9)
O82	0.0378 (6)	0.480 (4)	0.4869 (3)	0.158 (2)
O83	−0.1700 (6)	0.521 (4)	0.4569 (4)	0.172 (2)
C1	0.0854 (4)	0.513 (4)	0.3148 (2)	0.0605 (11)
H1	0.1656	0.4496	0.3520	0.073*
C3	−0.0643 (4)	0.367 (4)	0.1932 (3)	0.0649 (11)
H3A	−0.1403	0.4533	0.1719	0.078*
H3B	−0.0876	0.2303	0.1715	0.078*
C4	0.0463 (4)	0.446 (4)	0.1642 (2)	0.0565 (10)
H4	0.0175	0.5008	0.1046	0.068*
C5	0.1061 (4)	0.605 (4)	0.2330 (2)	0.0548 (10)
H5	0.1975	0.6348	0.2395	0.066*
C7	0.0305 (6)	0.868 (4)	0.2950 (3)	0.0952 (17)
H7A	−0.0496	0.9404	0.2899	0.114*
H7B	0.1025	0.9630	0.3130	0.114*
C8	0.0497 (5)	0.700 (4)	0.3605 (3)	0.0670 (11)
H8	0.1190	0.7322	0.4149	0.080*
C10	0.4899 (5)	−0.151 (4)	0.3995 (3)	0.0729 (13)
C11	0.6060 (5)	−0.142 (4)	0.4792 (3)	0.112 (2)
H11A	0.6213	−0.0044	0.4991	0.168*
H11B	0.6808	−0.1921	0.4655	0.168*
H11C	0.5910	−0.2243	0.5244	0.168*
C12	0.5425 (4)	−0.574 (4)	0.2703 (3)	0.0662 (12)
C13	0.6544 (4)	−0.711 (4)	0.2740 (3)	0.0902 (15)
H13A	0.6682	−0.8033	0.3223	0.135*
H13B	0.7315	−0.6313	0.2817	0.135*
H13C	0.6353	−0.7865	0.2204	0.135*
C14	0.3353 (5)	−0.473 (4)	−0.0211 (3)	0.0778 (14)
C15	0.3109 (6)	−0.673 (4)	−0.0662 (3)	0.1031 (18)
H15A	0.3250	−0.6620	−0.1221	0.155*
H15B	0.2225	−0.7137	−0.0745	0.155*
H15C	0.3693	−0.7721	−0.0311	0.155*
C41	0.1323 (4)	0.151 (4)	0.1152 (2)	0.0600 (11)
C42	0.2370 (4)	−0.002 (4)	0.1410 (2)	0.0518 (9)
C43	0.3335 (4)	0.005 (4)	0.2218 (2)	0.0544 (10)
H43	0.3348	0.1103	0.2605	0.065*
C44	0.4267 (4)	−0.144 (4)	0.2443 (2)	0.0535 (10)
C45	0.4261 (4)	−0.300 (4)	0.1875 (2)	0.0577 (10)
C46	0.3280 (4)	−0.310 (4)	0.1084 (2)	0.0567 (10)
C47	0.2337 (4)	−0.165 (4)	0.0849 (2)	0.0576 (10)
H47	0.1675	−0.1745	0.0316	0.069*

	U11	U22	U33	U12	U13	U23
N1	0.154 (5)	0.100 (4)	0.110 (4)	0.009 (4)	0.083 (4)	0.021 (3)
O2	0.100 (2)	0.0474 (17)	0.0766 (19)	−0.0117 (17)	0.0451 (17)	0.0010 (16)
O6	0.087 (2)	0.0495 (16)	0.0616 (16)	0.0065 (16)	0.0272 (14)	0.0106 (14)
O8	0.0588 (16)	0.0684 (19)	0.0611 (16)	−0.0001 (15)	0.0055 (14)	−0.0052 (16)
O9	0.086 (2)	0.139 (3)	0.0596 (17)	0.009 (3)	0.0203 (17)	0.007 (2)
O10	0.0723 (19)	0.074 (2)	0.0657 (17)	0.0082 (17)	0.0301 (15)	0.0047 (16)
O11	0.092 (2)	0.069 (2)	0.0833 (19)	−0.0089 (18)	0.0409 (18)	−0.0031 (18)
O12	0.099 (2)	0.0669 (19)	0.0561 (16)	−0.0005 (19)	0.0261 (15)	−0.0150 (16)
O13	0.169 (4)	0.120 (4)	0.081 (2)	−0.016 (4)	0.067 (3)	−0.010 (3)
O41	0.0613 (16)	0.0570 (17)	0.0504 (15)	0.0048 (15)	0.0076 (12)	−0.0069 (14)
O42	0.097 (2)	0.077 (2)	0.0528 (15)	0.0207 (19)	−0.0076 (16)	−0.0134 (17)
O81	0.093 (2)	0.074 (2)	0.0826 (19)	0.0111 (19)	0.0350 (18)	−0.002 (2)
O82	0.174 (5)	0.188 (6)	0.125 (4)	0.050 (5)	0.064 (4)	0.085 (4)
O83	0.195 (5)	0.151 (5)	0.233 (6)	0.010 (5)	0.161 (5)	0.039 (5)
C1	0.073 (3)	0.057 (3)	0.050 (2)	0.010 (3)	0.0168 (19)	0.008 (2)
C3	0.054 (2)	0.052 (2)	0.082 (3)	−0.001 (2)	0.012 (2)	0.004 (2)
C4	0.061 (2)	0.056 (2)	0.047 (2)	0.005 (2)	0.0093 (19)	−0.0003 (19)
C5	0.062 (2)	0.051 (2)	0.051 (2)	0.001 (2)	0.0169 (19)	0.0018 (19)
C7	0.156 (5)	0.059 (3)	0.085 (3)	0.019 (4)	0.059 (3)	0.001 (3)
C8	0.083 (3)	0.060 (3)	0.060 (2)	0.005 (2)	0.026 (2)	−0.001 (2)
C10	0.078 (3)	0.078 (3)	0.055 (3)	0.004 (3)	0.009 (2)	−0.011 (2)
C11	0.091 (3)	0.160 (6)	0.063 (3)	0.019 (4)	−0.008 (3)	−0.013 (4)
C12	0.071 (3)	0.057 (3)	0.071 (3)	−0.016 (2)	0.023 (2)	−0.008 (2)
C13	0.069 (3)	0.074 (3)	0.132 (4)	0.013 (3)	0.036 (3)	0.014 (3)
C14	0.077 (3)	0.099 (4)	0.056 (3)	0.009 (3)	0.018 (2)	−0.021 (3)
C15	0.114 (4)	0.109 (5)	0.083 (3)	0.006 (4)	0.026 (3)	−0.038 (4)
C41	0.082 (3)	0.052 (3)	0.044 (2)	0.001 (2)	0.017 (2)	−0.001 (2)
C42	0.061 (2)	0.048 (2)	0.045 (2)	−0.001 (2)	0.0135 (18)	−0.0041 (19)
C43	0.066 (2)	0.047 (2)	0.049 (2)	−0.008 (2)	0.0159 (19)	−0.0077 (19)
C44	0.052 (2)	0.057 (3)	0.048 (2)	−0.005 (2)	0.0107 (18)	−0.007 (2)
C45	0.059 (2)	0.061 (3)	0.056 (2)	0.006 (2)	0.021 (2)	0.006 (2)
C46	0.072 (3)	0.054 (2)	0.046 (2)	−0.006 (2)	0.021 (2)	−0.010 (2)
C47	0.071 (3)	0.057 (3)	0.0437 (19)	−0.004 (2)	0.0153 (19)	−0.005 (2)

O2—C1	1.42 (3)	C14—C15	1.49 (3)
O2—C3	1.427 (5)	C41—C42	1.48 (3)
O6—C5	1.42 (3)	C42—C43	1.389 (5)
O6—C7	1.405 (16)	C42—C47	1.40 (3)
O8—C10	1.367 (6)	C43—C44	1.37 (3)
O8—C44	1.404 (4)	C44—C45	1.37 (3)
O9—C10	1.187 (8)	C45—C46	1.379 (5)
O10—C12	1.36 (2)	C46—C47	1.36 (3)
O10—C45	1.39 (2)	C1—H1	0.9800
O11—C12	1.188 (6)	C3—H3A	0.9700
O12—C14	1.351 (6)	C3—H3B	0.9700
O12—C46	1.40 (3)	C4—H4	0.9800
O13—C14	1.18 (3)	C5—H5	0.9800
O41—C4	1.45 (3)	C7—H7A	0.9700
O41—C41	1.34 (3)	C7—H7B	0.9700
O42—C41	1.204 (5)	C8—H8	0.9800
O81—N1	1.38 (2)	C11—H11A	0.9600
O81—C8	1.442 (8)	C11—H11B	0.9600
O82—N1	1.189 (17)	C11—H11C	0.9600
O83—N1	1.197 (12)	C13—H13A	0.9600
C1—C5	1.527 (15)	C13—H13B	0.9600
C1—C8	1.55 (3)	C13—H13C	0.9600
C3—C4	1.505 (14)	C15—H15A	0.9600
C4—C5	1.51 (3)	C15—H15B	0.9600
C7—C8	1.50 (3)	C15—H15C	0.9600
C10—C11	1.487 (7)	C43—H43	0.9300
C12—C13	1.50 (2)	C47—H47	0.9300
C1—O2—C3	109.4 (13)	O12—C46—C47	121.4 (8)
C5—O6—C7	107.3 (10)	C45—C46—C47	121.0 (18)
C10—O8—C44	117.7 (4)	C42—C47—C46	119.7 (7)
C12—O10—C45	118.5 (7)	O2—C1—H1	111.00
C14—O12—C46	119 (2)	C5—C1—H1	111.00
C4—O41—C41	118.3 (7)	C8—C1—H1	111.00
N1—O81—C8	113.7 (11)	O2—C3—H3A	111.00
O81—N1—O82	117.9 (10)	O2—C3—H3B	111.00
O81—N1—O83	112.3 (12)	C4—C3—H3A	111.00
O82—N1—O83	129.8 (18)	C4—C3—H3B	111.00
O2—C1—C5	107.4 (8)	H3A—C3—H3B	109.00
O2—C1—C8	113.7 (8)	O41—C4—H4	113.00
C5—C1—C8	102.6 (18)	C3—C4—H4	113.00
O2—C3—C4	105.2 (7)	C5—C4—H4	113.00
O41—C4—C3	110.2 (19)	O6—C5—H5	114.00
O41—C4—C5	104.4 (8)	C1—C5—H5	114.00
C3—C4—C5	102.2 (8)	C4—C5—H5	114.00
O6—C5—C1	104.7 (10)	O6—C7—H7A	110.00
O6—C5—C4	108.1 (9)	O6—C7—H7B	110.00
C1—C5—C4	102.1 (17)	C8—C7—H7A	110.00
O6—C7—C8	107 (2)	C8—C7—H7B	110.00
O81—C8—C1	111.0 (18)	H7A—C7—H7B	109.00
O81—C8—C7	106.7 (12)	O81—C8—H8	111.00
C1—C8—C7	104.9 (9)	C1—C8—H8	111.00
O8—C10—O9	122.2 (4)	C7—C8—H8	111.00
O8—C10—C11	110.8 (5)	C10—C11—H11A	110.00
O9—C10—C11	126.9 (5)	C10—C11—H11B	109.00
O10—C12—O11	123.5 (18)	C10—C11—H11C	109.00
O10—C12—C13	108.9 (8)	H11A—C11—H11B	109.00
O11—C12—C13	127.6 (19)	H11A—C11—H11C	110.00
O12—C14—O13	122 (2)	H11B—C11—H11C	109.00
O12—C14—C15	110.4 (19)	C12—C13—H13A	110.00
O13—C14—C15	127.6 (8)	C12—C13—H13B	109.00
O41—C41—O42	123 (2)	C12—C13—H13C	109.00
O41—C41—C42	111.7 (8)	H13A—C13—H13B	110.00
O42—C41—C42	125 (2)	H13A—C13—H13C	109.00
C41—C42—C43	121.7 (17)	H13B—C13—H13C	110.00
C41—C42—C47	118.9 (7)	C14—C15—H15A	109.00
C43—C42—C47	119.3 (17)	C14—C15—H15B	109.00
C42—C43—C44	119.8 (18)	C14—C15—H15C	109.00
O8—C44—C43	120.5 (18)	H15A—C15—H15B	109.00
O8—C44—C45	118.8 (17)	H15A—C15—H15C	110.00
C43—C44—C45	120.7 (7)	H15B—C15—H15C	109.00
O10—C45—C44	121.7 (7)	C42—C43—H43	120.00
O10—C45—C46	118.7 (16)	C44—C43—H43	120.00
C44—C45—C46	119.4 (17)	C42—C47—H47	120.00
O12—C46—C45	117.1 (18)	C46—C47—H47	120.00
C3—O2—C1—C5	−2(2)	O2—C1—C8—C7	−106.1 (12)
C3—O2—C1—C8	111.2 (14)	C5—C1—C8—O81	124.5 (9)
C1—O2—C3—C4	24 (2)	C5—C1—C8—C7	9.6 (7)
C7—O6—C5—C1	38.2 (16)	O2—C3—C4—O41	75 (2)
C7—O6—C5—C4	146.4 (11)	O2—C3—C4—C5	−36 (2)
C5—O6—C7—C8	−32.0 (12)	O41—C4—C5—O6	168.9 (10)
C44—O8—C10—O9	1(4)	O41—C4—C5—C1	−81.0 (10)
C44—O8—C10—C11	−180 (2)	C3—C4—C5—O6	−76.2 (15)
C10—O8—C44—C43	63 (3)	C3—C4—C5—C1	33.9 (15)
C10—O8—C44—C45	−118 (2)	O6—C7—C8—O81	−105.3 (13)
C45—O10—C12—O11	1(3)	O6—C7—C8—C1	12.6 (7)
C45—O10—C12—C13	178.2 (15)	O41—C41—C42—C43	2(2)
C12—O10—C45—C44	70 (3)	O41—C41—C42—C47	177.7 (14)
C12—O10—C45—C46	−115.3 (16)	O42—C41—C42—C43	−177.5 (16)
C46—O12—C14—O13	4.0 (11)	O42—C41—C42—C47	−2(2)
C46—O12—C14—C15	−174.5 (6)	C41—C42—C43—C44	177.9 (14)
C14—O12—C46—C45	−118.2 (11)	C47—C42—C43—C44	2(2)
C14—O12—C46—C47	69.8 (11)	C41—C42—C47—C46	−178.7 (13)
C41—O41—C4—C3	83.5 (13)	C43—C42—C47—C46	−3(2)
C41—O41—C4—C5	−167.3 (14)	C42—C43—C44—O8	179.3 (14)
C4—O41—C41—O42	4(2)	C42—C43—C44—C45	0(2)
C4—O41—C41—C42	−175.7 (13)	O8—C44—C45—O10	−7(2)
N1—O81—C8—C1	78.0 (16)	O8—C44—C45—C46	178.8 (14)
N1—O81—C8—C7	−168.3 (17)	C43—C44—C45—O10	172.3 (15)
C8—O81—N1—O82	0(3)	C43—C44—C45—C46	−2(2)
C8—O81—N1—O83	−178 (2)	O10—C45—C46—O12	15 (2)
O2—C1—C5—O6	91.8 (18)	O10—C45—C46—C47	−173.0 (15)
O2—C1—C5—C4	−20.9 (17)	C44—C45—C46—O12	−170.4 (13)
C8—C1—C5—O6	−28.4 (11)	C44—C45—C46—C47	2(2)
C8—C1—C5—C4	−141.0 (9)	O12—C46—C47—C42	172.6 (13)
O2—C1—C8—O81	8.8 (14)	C45—C46—C47—C42	1(2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.98	2.56	3.365 (13)	139
C4—H4···O42ii	0.98	2.53	3.507 (15)	177
C43—H43···O11i	0.93	2.51	3.25 (3)	136
C47—H47···O42iii	0.93	2.52	3.314 (14)	144
C11—H11B···O83iv	0.96	2.52	3.39 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.98	2.56	3.365 (13)	139
C4—H4⋯O42ii	0.98	2.53	3.507 (15)	177
C43—H43⋯O11i	0.93	2.51	3.25 (3)	136
C47—H47⋯O42iii	0.93	2.52	3.314 (14)	144
C11—H11B⋯O83iv	0.96	2.52	3.39 (3)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C42–C47 phenyl ring.