(1S,4S,5S,8R)-8-Nitro­oxy-2,6-dioxa­bicyclo­[3.3.0]octan-4-yl 3,4,5-triacetoxy­benzoate

Zhang, Y.; Wang, P.-A.; Zhang, M.-Y.; Sun, X.-L.

doi:10.1107/S1600536809042524

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2849

https://doi.org/10.1107/S1600536809042524

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(1S,4S,5S,8R)-8-Nitrooxy-2,6-dioxabicyclo[3.3.0]octan-4-yl 3,4,5-triacetoxybenzoate

Yue Zhang,^a Ping-An Wang,^a Meng-Yao Zhang ^a and Xiao-Li Sun ^a ^*

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032, Xi-An, People's Republic of China
^*Correspondence e-mail: xiaoli_sun@yahoo.cn

(Received 9 October 2009; accepted 15 October 2009; online 23 October 2009)

In the title compound, C₁₉H₁₉NO₁₃, one of the two fused furanose rings adopts an envelope conformation whereas the other displays a twisted conformation. The crystal structure is stabilized by intermolecular C—H⋯π interactions between a methine H atom and the triacetoxyphenyl ring of an adjacent molecule, and by weak non-classical intermolecular 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_r = 469.35
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.02
2112 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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⋯O83^iv	0.96	2.52	3.39 (3)	151
Symmetry codes: (i) x, y+1, z; (ii) $[-x, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z]$ ; (iv) x+1, y-1, z. Cg1 is the centroid of the C42–C47 phenyl ring.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042524/dn2497Isup2.hkl

checkCIF report

Comment top

The title compound is synthesized by esterification of 3,4,5-triacetoxybenzoic acid with Isosorbide Mononitrate.It can be rapidly metabolized to 3,4,5-trihydroxybenzoic acid and Isosorbide Mononitrate in vivo(Carini et al.,2002). 3,4,5-trihydroxybenzoic acid is a bioactivesubstance which can scavenge oxygen free radicals and Isosorbide Mononitrate is a classical nitric oxide-donor drug. This bifunctional molecule may have better bioactivity but do bring fewer side effect.

The molecule is built up from the isosorbide mononitrate skeleton substituted on C4 by the 3,4,5-triacetoxybenzoate (Fig. 1). The two fused furanose rings have slightly different conformation. Indeed, the Cremer & Pople (1975) puckering parameters for the C1-O2-C3-C4-C5 ring are Q(2) = 0.359 (4)Å and φ(2) = 289.1 (6)° whereas those for the C5-O6-C7-C8-C1 ring are Q(2) = 0.334 (4)Å and φ(2) = 343.4 (7)°. These values indicate that these two rings have different extent of puckering caused by the different substituent group in the ring. The pseudorotation parameters (Rao et al. 1981) for C1-O2-C3-C4-C5 ring are P = 20.8 (4)° & τ(M) = 37.3 (2)° for the C5—C4 reference bond with the closest pucker descriptor being enveloped on C(4) and those for C5-O6-C7-C8-C1 ring are P = 75.4 (4)° and τ(M) = 35.7 (3)° for the C8—C1 reference bond with the closest puckering descriptor being twisted on C5—O6.

Owing to the know absolute configuration of the starting isosorbide mononitrate, the absolute configuration of the title compound could be deduced to be 1S,4S,5S,8R.

The molecular packing is stabilized by weak non-classical intermolecular C–H···O hydrogen bonds and by intermolecular C–H···π interaction between methine H atom of perhydrofurofuranyl system and the triacetoxyphenyl ring of an adjacent molecule (Table 1, Cg1 is the centroid of C42—C47 phenyl ring).

Related literature top

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).

Cg1 is the centroid of the C42–C47 phenyl ring.

Experimental top

3,4,5-triacetoxybenzoic acid(2.96 g, 10 mmol), Isosorbide Mononitrate (1.91 g, 10 mmol, CAS No:16051–77-7, [α]_D=168 ° (c=1.0, EtOH) and DMAP (0.24 g, 1 mmol) were dissolved in 100 ml dry THF, then DCC (4.12 g, 10 mmol) was added to the solution at 0°C. The mixture was stirred at room temperature for 5 h. The resulting mixture was filtered and concentrated in vacuo. The crude product was purified by column chromatography over silica gelusing ethyl acetate/n-hexane (7:3) as eluent. Yield: 4.21 g (85%). Single crystals of the title compound suitable for X-ray diffraction was recrystallized from hexane/ethyl acetate (1:1).

Structure description top

Owing to the know absolute configuration of the starting isosorbide mononitrate, the absolute configuration of the title compound could be deduced to be 1S,4S,5S,8R.

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).

Cg1 is the centroid of the C42–C47 phenyl ring.

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top

Fig. 1. Molecular structure of the title compound (I), showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(1S,4S,5S,8R)-8-Nitrooxy-2,6- dioxabicyclo[3.3.0]octan-4-yl 3,4,5-triacetoxybenzoate top

Crystal data top

C₁₉H₁₉NO₁₃	F(000) = 488
M_r = 469.35	D_x = 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

Data collection top

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

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0523P)²] where P = (F_o² + 2F_c²)/3
2112 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₉H₁₉NO₁₃	V = 1087.8 (3) Å³
M_r = 469.35	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.8053 (19) Å	µ = 0.12 mm⁻¹
b = 6.5941 (12) Å	T = 296 K
c = 16.075 (3) Å	0.31 × 0.25 × 0.14 mm
β = 108.243 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2112 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1394 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.983	R_int = 0.023
5474 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
2112 reflections	Δρ_min = −0.14 e Å⁻³
301 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O83^iv	0.96	2.52	3.39 (3)	151

Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z; (iii) −x, y−1/2, −z; (iv) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₁₃
M_r	469.35
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	10.8053 (19), 6.5941 (12), 16.075 (3)
β (°)	108.243 (3)
V (Å³)	1087.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.31 × 0.25 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.962, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	5474, 2112, 1394
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.02
No. of reflections	2112
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.14

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

O2—C1	1.42 (3)	O12—C14	1.351 (6)
O2—C3	1.427 (5)	O12—C46	1.40 (3)
O6—C5	1.42 (3)	O13—C14	1.18 (3)
O6—C7	1.405 (16)	O41—C4	1.45 (3)
O8—C10	1.367 (6)	O41—C41	1.34 (3)
O8—C44	1.404 (4)	O42—C41	1.204 (5)
O9—C10	1.187 (8)	O81—N1	1.38 (2)
O10—C12	1.36 (2)	O81—C8	1.442 (8)
O10—C45	1.39 (2)	O82—N1	1.189 (17)
O11—C12	1.188 (6)	O83—N1	1.197 (12)

C1—O2—C3	109.4 (13)	O81—C8—C7	106.7 (12)
C5—O6—C7	107.3 (10)	O8—C10—O9	122.2 (4)
C10—O8—C44	117.7 (4)	O8—C10—C11	110.8 (5)
C12—O10—C45	118.5 (7)	O9—C10—C11	126.9 (5)
C14—O12—C46	119 (2)	O10—C12—O11	123.5 (18)
C4—O41—C41	118.3 (7)	O10—C12—C13	108.9 (8)
N1—O81—C8	113.7 (11)	O11—C12—C13	127.6 (19)
O81—N1—O82	117.9 (10)	O12—C14—O13	122 (2)
O81—N1—O83	112.3 (12)	O12—C14—C15	110.4 (19)
O82—N1—O83	129.8 (18)	O13—C14—C15	127.6 (8)
O2—C1—C5	107.4 (8)	O41—C41—O42	123 (2)
O2—C1—C8	113.7 (8)	O41—C41—C42	111.7 (8)
O2—C3—C4	105.2 (7)	O42—C41—C42	125 (2)
O41—C4—C3	110.2 (19)	O8—C44—C43	120.5 (18)
O41—C4—C5	104.4 (8)	O8—C44—C45	118.8 (17)
O6—C5—C1	104.7 (10)	O10—C45—C44	121.7 (7)
O6—C5—C4	108.1 (9)	O10—C45—C46	118.7 (16)
O6—C7—C8	107 (2)	O12—C46—C45	117.1 (18)
O81—C8—C1	111.0 (18)	O12—C46—C47	121.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1ⁱ	0.98	2.56	3.365 (13)	139.0
C4—H4···O42ⁱⁱ	0.98	2.53	3.507 (15)	176.6
C43—H43···O11ⁱ	0.93	2.51	3.25 (3)	136.1
C47—H47···O42ⁱⁱⁱ	0.93	2.52	3.314 (14)	144.1
C11—H11B···O83^iv	0.96	2.52	3.39 (3)	150.5

Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z; (iii) −x, y−1/2, −z; (iv) x+1, y−1, z.

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20802092) for financial support.

References

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

(1S,4S,5S,8R)-8-Nitro­­oxy-2,6-dioxa­bi­cyclo­[3.3.0]octan-4-yl 3,4,5-tri­acet­oxy­benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1S,4S,5S,8R)-8-Nitrooxy-2,6-dioxabicyclo[3.3.0]octan-4-yl 3,4,5-triacetoxybenzoate