(4R*,5R*)-Diethyl 2-(4-nitro-phen-yl)-1,3-dioxolane-4,5-dicarboxyl-ate.

In the title compound, C(15)H(17)NO(8), the nitro group is essentially coplanar with the aromatic ring [dihedral angle = 6.4 (3) Å]. The five-membered ring has a twist conformation. In the crystal, C-H⋯O inter-actions link the mol-ecules into a helical chain propagating along [010].

Related literature

For the synthesis of the title compound, see: Kim et al. (1994 ▶). For the use of (2S,3S)-diethyl 2,3-O-alkyl­tartrate analogues as inter­mediates in organic synthesis, see: Pandey et al. (1997 ▶). For typical bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H17NO8

M = 339.30

Monoclinic,

a = 12.261 (3) Å

b = 4.5200 (9) Å

c = 15.656 (3) Å

β = 112.27 (3)°

V = 802.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.966, T max = 0.989

3062 measured reflections

1660 independent reflections

1364 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.142

S = 1.01

1660 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201118X/su2384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201118X/su2384Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201118X/su2384Isup3.cml

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

C15H17NO8	F(000) = 356
Mr = 339.30	Dx = 1.403 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 12.261 (3) Å	θ = 9–13°
b = 4.5200 (9) Å	µ = 0.12 mm−1
c = 15.656 (3) Å	T = 293 K
β = 112.27 (3)°	Block, colourless
V = 802.9 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 2

Enraf-Nonius CAD-4 diffractometer	1364 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 25.3°, θmin = 1.4°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −5→5
Tmin = 0.966, Tmax = 0.989	l = −18→17
3062 measured reflections	3 standard reflections every 200 reflections
1660 independent reflections	intensity decay: 1%

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.1P)2 + 0.070P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1660 reflections	Δρmax = 0.21 e Å−3
218 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (9)

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.

	x	y	z	Uiso*/Ueq
N1	0.1597 (5)	0.1051 (17)	0.6035 (3)	0.1016 (18)
C1	0.3496 (4)	−0.1471 (14)	0.4814 (3)	0.0770 (14)
H1A	0.4154	−0.2670	0.4932	0.092*
O1	0.0820 (6)	0.276 (2)	0.5904 (4)	0.163 (3)
C2	0.3039 (4)	−0.1052 (17)	0.5489 (3)	0.0902 (18)
H2A	0.3396	−0.1929	0.6066	0.108*
O2	0.2028 (4)	−0.0395 (18)	0.6735 (3)	0.146 (3)
O3	0.26487 (19)	−0.1203 (6)	0.23682 (14)	0.0483 (6)
C3	0.2075 (4)	0.0631 (14)	0.5303 (3)	0.0703 (12)
O4	0.40116 (19)	0.2240 (6)	0.31395 (14)	0.0465 (6)
C4	0.1556 (4)	0.2006 (17)	0.4495 (3)	0.0924 (19)
H4A	0.0895	0.3184	0.4387	0.111*
O5	0.5315 (2)	0.1545 (8)	0.14859 (18)	0.0685 (8)
C5	0.2020 (4)	0.1647 (15)	0.3817 (3)	0.0855 (17)
H5A	0.1675	0.2616	0.3254	0.103*
C6	0.2981 (3)	−0.0121 (9)	0.3972 (2)	0.0490 (9)
O6	0.5589 (3)	−0.1270 (9)	0.2711 (2)	0.0884 (11)
C7	0.3507 (3)	−0.0501 (8)	0.3259 (2)	0.0469 (8)
H7A	0.4116	−0.2038	0.3455	0.056*
C8	0.4003 (3)	0.2225 (8)	0.2239 (2)	0.0445 (8)
H8A	0.3970	0.4254	0.2010	0.053*
O7	0.1014 (2)	0.2755 (6)	0.15578 (16)	0.0555 (7)
C9	0.2829 (3)	0.0569 (8)	0.1691 (2)	0.0452 (8)
H9A	0.2942	−0.0709	0.1226	0.054*
O8	0.1850 (2)	0.4257 (7)	0.05872 (16)	0.0650 (8)
C10	0.5053 (3)	0.0613 (9)	0.2180 (3)	0.0525 (9)
C11	0.6333 (4)	0.0176 (15)	0.1381 (3)	0.0895 (16)
H11A	0.6229	−0.1952	0.1325	0.107*
H11B	0.7040	0.0595	0.1917	0.107*
C12	0.6445 (5)	0.1387 (18)	0.0547 (4)	0.107 (2)
H12A	0.7100	0.0469	0.0457	0.161*
H12B	0.6573	0.3484	0.0616	0.161*
H12C	0.5735	0.1000	0.0022	0.161*
C13	0.1838 (3)	0.2735 (8)	0.1218 (2)	0.0449 (8)
C14	0.0027 (4)	0.4800 (12)	0.1144 (3)	0.0712 (12)
H14A	0.0301	0.6610	0.0960	0.085*
H14B	−0.0562	0.3910	0.0601	0.085*
C15	−0.0484 (5)	0.5452 (19)	0.1824 (4)	0.117 (2)
H15A	−0.1132	0.6799	0.1563	0.175*
H15B	0.0103	0.6335	0.2359	0.175*
H15C	−0.0761	0.3653	0.1998	0.175*

	U11	U22	U33	U12	U13	U23
N1	0.105 (3)	0.139 (5)	0.084 (3)	−0.026 (4)	0.062 (3)	−0.016 (3)
C1	0.071 (2)	0.095 (4)	0.068 (2)	0.019 (3)	0.030 (2)	0.030 (3)
O1	0.183 (5)	0.223 (8)	0.135 (4)	0.052 (7)	0.119 (4)	0.004 (5)
C2	0.093 (3)	0.125 (5)	0.056 (2)	0.000 (4)	0.032 (2)	0.028 (3)
O2	0.176 (4)	0.200 (7)	0.094 (2)	−0.031 (5)	0.089 (3)	0.015 (4)
O3	0.0611 (13)	0.0358 (12)	0.0482 (12)	−0.0079 (12)	0.0209 (10)	−0.0006 (10)
C3	0.073 (2)	0.091 (3)	0.056 (2)	−0.022 (3)	0.0355 (19)	−0.011 (2)
O4	0.0525 (12)	0.0379 (13)	0.0504 (12)	−0.0032 (11)	0.0208 (9)	−0.0071 (11)
C4	0.088 (3)	0.130 (5)	0.072 (3)	0.036 (4)	0.045 (2)	0.007 (4)
O5	0.0702 (16)	0.073 (2)	0.0773 (16)	0.0163 (16)	0.0448 (13)	0.0028 (16)
C5	0.090 (3)	0.112 (5)	0.060 (2)	0.045 (3)	0.036 (2)	0.021 (3)
C6	0.0488 (17)	0.048 (2)	0.0468 (17)	−0.0029 (17)	0.0141 (14)	0.0011 (16)
O6	0.090 (2)	0.078 (2)	0.117 (2)	0.034 (2)	0.0619 (19)	0.033 (2)
C7	0.0506 (17)	0.0374 (18)	0.0508 (17)	0.0003 (16)	0.0169 (14)	0.0011 (15)
C8	0.0494 (17)	0.0367 (17)	0.0495 (16)	−0.0036 (16)	0.0212 (14)	−0.0032 (16)
O7	0.0547 (13)	0.0584 (17)	0.0582 (13)	0.0070 (13)	0.0267 (11)	0.0119 (13)
C9	0.0597 (19)	0.0338 (17)	0.0486 (16)	−0.0033 (16)	0.0279 (15)	−0.0046 (15)
O8	0.0735 (16)	0.071 (2)	0.0550 (13)	0.0023 (16)	0.0290 (12)	0.0172 (15)
C10	0.058 (2)	0.043 (2)	0.062 (2)	−0.0007 (19)	0.0291 (17)	−0.0052 (19)
C11	0.090 (3)	0.095 (4)	0.109 (3)	0.022 (3)	0.066 (3)	−0.007 (3)
C12	0.112 (4)	0.124 (6)	0.118 (4)	0.014 (4)	0.081 (3)	−0.009 (4)
C13	0.0490 (17)	0.0425 (19)	0.0401 (15)	−0.0088 (15)	0.0135 (14)	−0.0045 (15)
C14	0.061 (2)	0.073 (3)	0.078 (3)	0.017 (2)	0.0242 (19)	0.014 (2)
C15	0.100 (4)	0.136 (7)	0.133 (4)	0.057 (5)	0.065 (3)	0.027 (5)

N1—O1	1.183 (9)	C7—H7A	0.9800
N1—O2	1.212 (8)	C8—C10	1.512 (5)
N1—C3	1.483 (6)	C8—C9	1.560 (4)
C1—C6	1.370 (5)	C8—H8A	0.9800
C1—C2	1.384 (6)	O7—C13	1.309 (4)
C1—H1A	0.9300	O7—C14	1.465 (5)
C2—C3	1.341 (8)	C9—C13	1.517 (5)
C2—H2A	0.9300	C9—H9A	0.9800
O3—C9	1.411 (4)	O8—C13	1.208 (4)
O3—C7	1.428 (4)	C11—C12	1.470 (7)
C3—C4	1.335 (7)	C11—H11A	0.9700
O4—C8	1.406 (4)	C11—H11B	0.9700
O4—C7	1.428 (4)	C12—H12A	0.9600
C4—C5	1.391 (6)	C12—H12B	0.9600
C4—H4A	0.9300	C12—H12C	0.9600
O5—C10	1.314 (5)	C14—C15	1.455 (7)
O5—C11	1.458 (5)	C14—H14A	0.9700
C5—C6	1.367 (6)	C14—H14B	0.9700
C5—H5A	0.9300	C15—H15A	0.9600
C6—C7	1.497 (5)	C15—H15B	0.9600
O6—C10	1.197 (5)	C15—H15C	0.9600
O1—N1—O2	123.7 (5)	O3—C9—C13	114.1 (3)
O1—N1—C3	118.6 (6)	O3—C9—C8	103.5 (2)
O2—N1—C3	117.7 (6)	C13—C9—C8	111.1 (3)
C6—C1—C2	120.0 (5)	O3—C9—H9A	109.3
C6—C1—H1A	120.0	C13—C9—H9A	109.3
C2—C1—H1A	120.0	C8—C9—H9A	109.3
C3—C2—C1	119.4 (4)	O6—C10—O5	124.1 (4)
C3—C2—H2A	120.3	O6—C10—C8	123.8 (3)
C1—C2—H2A	120.3	O5—C10—C8	112.1 (3)
C9—O3—C7	109.9 (3)	O5—C11—C12	108.3 (4)
C4—C3—C2	122.3 (4)	O5—C11—H11A	110.0
C4—C3—N1	119.1 (5)	C12—C11—H11A	110.0
C2—C3—N1	118.6 (5)	O5—C11—H11B	110.0
C8—O4—C7	106.7 (3)	C12—C11—H11B	110.0
C3—C4—C5	118.9 (5)	H11A—C11—H11B	108.4
C3—C4—H4A	120.6	C11—C12—H12A	109.5
C5—C4—H4A	120.6	C11—C12—H12B	109.5
C10—O5—C11	116.5 (4)	H12A—C12—H12B	109.5
C6—C5—C4	120.4 (4)	C11—C12—H12C	109.5
C6—C5—H5A	119.8	H12A—C12—H12C	109.5
C4—C5—H5A	119.8	H12B—C12—H12C	109.5
C5—C6—C1	118.9 (4)	O8—C13—O7	125.3 (3)
C5—C6—C7	121.4 (3)	O8—C13—C9	120.8 (3)
C1—C6—C7	119.7 (3)	O7—C13—C9	113.9 (3)
O4—C7—O3	105.1 (3)	C15—C14—O7	108.5 (4)
O4—C7—C6	109.2 (3)	C15—C14—H14A	110.0
O3—C7—C6	112.8 (3)	O7—C14—H14A	110.0
O4—C7—H7A	109.9	C15—C14—H14B	110.0
O3—C7—H7A	109.9	O7—C14—H14B	110.0
C6—C7—H7A	109.9	H14A—C14—H14B	108.4
O4—C8—C10	112.4 (3)	C14—C15—H15A	109.5
O4—C8—C9	102.0 (2)	C14—C15—H15B	109.5
C10—C8—C9	111.4 (3)	H15A—C15—H15B	109.5
O4—C8—H8A	110.3	C14—C15—H15C	109.5
C10—C8—H8A	110.3	H15A—C15—H15C	109.5
C9—C8—H8A	110.3	H15B—C15—H15C	109.5
C13—O7—C14	117.5 (3)
C6—C1—C2—C3	1.4 (9)	C7—O4—C8—C10	−83.6 (3)
C1—C2—C3—C4	−2.1 (10)	C7—O4—C8—C9	35.8 (3)
C1—C2—C3—N1	179.9 (6)	C7—O3—C9—C13	−114.2 (3)
O1—N1—C3—C4	−5.3 (10)	C7—O3—C9—C8	6.7 (3)
O2—N1—C3—C4	174.5 (6)	O4—C8—C9—O3	−25.9 (3)
O1—N1—C3—C2	172.7 (7)	C10—C8—C9—O3	94.2 (3)
O2—N1—C3—C2	−7.5 (9)	O4—C8—C9—C13	97.1 (3)
C2—C3—C4—C5	0.9 (10)	C10—C8—C9—C13	−142.9 (3)
N1—C3—C4—C5	178.9 (6)	C11—O5—C10—O6	−0.6 (6)
C3—C4—C5—C6	1.0 (10)	C11—O5—C10—C8	178.6 (4)
C4—C5—C6—C1	−1.6 (9)	O4—C8—C10—O6	24.7 (5)
C4—C5—C6—C7	−179.0 (5)	C9—C8—C10—O6	−89.0 (4)
C2—C1—C6—C5	0.5 (8)	O4—C8—C10—O5	−154.5 (3)
C2—C1—C6—C7	177.8 (5)	C9—C8—C10—O5	91.7 (4)
C8—O4—C7—O3	−32.8 (3)	C10—O5—C11—C12	177.1 (5)
C8—O4—C7—C6	−154.0 (2)	C14—O7—C13—O8	−0.4 (5)
C9—O3—C7—O4	14.8 (3)	C14—O7—C13—C9	179.6 (3)
C9—O3—C7—C6	133.7 (3)	O3—C9—C13—O8	−175.6 (3)
C5—C6—C7—O4	67.0 (5)	C8—C9—C13—O8	67.8 (4)
C1—C6—C7—O4	−110.3 (4)	O3—C9—C13—O7	4.4 (4)
C5—C6—C7—O3	−49.4 (5)	C8—C9—C13—O7	−112.2 (3)
C1—C6—C7—O3	133.3 (4)	C13—O7—C14—C15	−155.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O8i	0.96	2.50	3.356 (7)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O8i	0.96	2.50	3.356 (7)	149

Symmetry code: (i) .