2-(Methoxy-meth-oxy)-1-(4-oxobicyclo-[3.1.0]hexan-1-yl)ethyl 4-nitro-benzoate.

In the title compound, C(17)H(19)NO(7), the cyclo-pentane ring is in an envelope conformation in which the methyl-ene group forming the flap is cis to the cyclo-propane group. The relative configuration between the 4-nitro-benzo-yloxy substituent on the side chain and the cyclo-propane ring is trans and the methoxy-lmethyl group adopts the expected conformation in which the two O atoms are gauche to one another.

Related literature

For the synthesis of mimetics of biologically important furan­oside rings, see: Callam & Lowary (2000 ▶, 2001 ▶); Callam et al. (2001 ▶); Centrone & Lowary (2002 ▶). For examples of crystal structures of bicyclo­[3.1.0]hexane systems, see; Gurskaya et al. (1990 ▶, 1996 ▶); Gallucci et al. (2000 ▶); Garcia et al. (1992 ▶); Guthrie et al. (1981 ▶); Màrton-Merész et al. (1983 ▶); Biswas et al. (1996 ▶); Bai et al. (2004 ▶). For related literature, see: Hamon & Shirley (1988 ▶); Li & Lowary (2008 ▶); Wolfe (1972 ▶).

Experimental

Crystal data

C17H19NO7

M = 349.33

Triclinic,

a = 8.3387 (5) Å

b = 10.1389 (6) Å

c = 10.4935 (6) Å

α = 98.5259 (8)°

β = 100.4967 (8)°

γ = 101.1562 (7)°

V = 840.22 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 193 (2) K

0.52 × 0.50 × 0.47 mm

Data collection

Bruker PLATFORM diffractometer SMART 1000 CCD area-detector

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.946, T max = 0.951

7436 measured reflections

3825 independent reflections

3476 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.05

3825 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706686X/lh2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706686X/lh2582Isup2.hkl

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

C17H19NO7	Z = 2
Mr = 349.33	F000 = 368
Triclinic, P1	Dx = 1.381 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3387 (5) Å	Cell parameters from 7818 reflections
b = 10.1389 (6) Å	θ = 2.6–27.5º
c = 10.4935 (6) Å	µ = 0.11 mm−1
α = 98.5259 (8)º	T = 193 (2) K
β = 100.4967 (8)º	Fragment, colourless
γ = 101.1562 (7)º	0.52 × 0.50 × 0.47 mm
V = 840.22 (9) Å3

Bruker PLATFORM diffractometer/SMART 1000 CCD area-detector	3825 independent reflections
Radiation source: fine-focus sealed tube	3476 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.009
Detector resolution: 8.192 pixels mm-1	θmax = 27.5º
T = 193(2) K	θmin = 2.0º
ω scans	h = −10→10
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	k = −13→13
Tmin = 0.946, Tmax = 0.951	l = −13→13
7436 measured reflections

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.1568P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.013
3825 reflections	Δρmax = 0.31 e Å−3
227 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.09546 (12)	0.07242 (11)	0.73892 (11)	0.0553 (3)
O2	0.27720 (9)	0.22849 (8)	0.35099 (8)	0.03307 (19)
O3	0.36653 (10)	0.48159 (9)	0.28812 (8)	0.0367 (2)
O4	0.19060 (11)	0.53166 (10)	0.10951 (9)	0.0469 (2)
O5	0.54644 (13)	0.22855 (12)	0.42875 (11)	0.0650 (3)
O6	0.43439 (13)	−0.32377 (10)	−0.08313 (10)	0.0534 (3)
O7	0.18678 (14)	−0.29604 (11)	−0.15763 (10)	0.0602 (3)
N	0.32018 (14)	−0.26560 (10)	−0.07714 (10)	0.0398 (2)
C1	0.16536 (13)	0.31828 (10)	0.53155 (10)	0.0302 (2)
C2	−0.01745 (14)	0.24464 (13)	0.47296 (12)	0.0384 (3)
H2A	−0.0267	0.1788	0.3908	0.046*
H2B	−0.0864	0.3112	0.4527	0.046*
C3	−0.07499 (15)	0.16936 (15)	0.57953 (14)	0.0458 (3)
H3A	−0.1392	0.2220	0.6298	0.055*
H3B	−0.1466	0.0775	0.5389	0.055*
C4	0.08438 (15)	0.15744 (12)	0.66935 (12)	0.0391 (3)
C5	0.22604 (14)	0.26104 (11)	0.65309 (11)	0.0344 (2)
H5	0.3421	0.2453	0.6717	0.041*
C6	0.19962 (16)	0.40686 (12)	0.66433 (11)	0.0379 (3)
H6A	0.1024	0.4264	0.6994	0.046*
H6B	0.3003	0.4831	0.6890	0.046*
C7	0.28480 (13)	0.35255 (10)	0.44415 (10)	0.0294 (2)
H7	0.4011	0.3873	0.4990	0.035*
C8	0.24071 (13)	0.45645 (11)	0.36257 (11)	0.0331 (2)
H8A	0.1291	0.4203	0.3028	0.040*
H8B	0.2384	0.5422	0.4206	0.040*
C9	0.34064 (15)	0.57459 (13)	0.20414 (12)	0.0414 (3)
H9A	0.3415	0.6636	0.2582	0.050*
H9B	0.4348	0.5892	0.1586	0.050*
C10	0.18474 (19)	0.41015 (17)	0.01905 (14)	0.0547 (4)
H10A	0.0777	0.3849	−0.0454	0.066*
H10B	0.1956	0.3356	0.0674	0.066*
H10C	0.2769	0.4264	−0.0270	0.066*
C11	0.41618 (14)	0.18250 (11)	0.35071 (11)	0.0332 (2)
C12	0.38783 (13)	0.06385 (10)	0.23884 (10)	0.0297 (2)
C13	0.52157 (14)	0.00427 (11)	0.22180 (11)	0.0328 (2)
H13	0.6274	0.0381	0.2811	0.039*
C14	0.50030 (14)	−0.10469 (11)	0.11803 (11)	0.0328 (2)
H14	0.5905	−0.1461	0.1051	0.039*
C15	0.34449 (14)	−0.15100 (10)	0.03447 (10)	0.0317 (2)
C16	0.20974 (15)	−0.09435 (12)	0.04924 (12)	0.0385 (3)
H16	0.1041	−0.1290	−0.0101	0.046*
C17	0.23241 (14)	0.01446 (12)	0.15285 (12)	0.0361 (2)
H17	0.1416	0.0553	0.1651	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0480 (5)	0.0566 (6)	0.0701 (7)	0.0130 (4)	0.0196 (5)	0.0295 (5)
O2	0.0283 (4)	0.0314 (4)	0.0349 (4)	0.0070 (3)	0.0051 (3)	−0.0062 (3)
O3	0.0310 (4)	0.0466 (5)	0.0339 (4)	0.0100 (3)	0.0069 (3)	0.0108 (3)
O4	0.0386 (5)	0.0592 (6)	0.0436 (5)	0.0144 (4)	0.0021 (4)	0.0154 (4)
O5	0.0436 (5)	0.0701 (7)	0.0627 (6)	0.0286 (5)	−0.0171 (5)	−0.0310 (5)
O6	0.0586 (6)	0.0459 (5)	0.0544 (6)	0.0203 (4)	0.0154 (5)	−0.0091 (4)
O7	0.0642 (7)	0.0551 (6)	0.0463 (5)	0.0174 (5)	−0.0092 (5)	−0.0168 (4)
N	0.0500 (6)	0.0325 (5)	0.0347 (5)	0.0094 (4)	0.0092 (4)	−0.0001 (4)
C1	0.0295 (5)	0.0306 (5)	0.0287 (5)	0.0084 (4)	0.0044 (4)	0.0006 (4)
C2	0.0277 (5)	0.0490 (6)	0.0357 (6)	0.0080 (5)	0.0045 (4)	0.0033 (5)
C3	0.0306 (6)	0.0577 (8)	0.0489 (7)	0.0069 (5)	0.0108 (5)	0.0110 (6)
C4	0.0372 (6)	0.0409 (6)	0.0414 (6)	0.0102 (5)	0.0132 (5)	0.0075 (5)
C5	0.0317 (5)	0.0365 (5)	0.0335 (5)	0.0081 (4)	0.0040 (4)	0.0052 (4)
C6	0.0446 (6)	0.0356 (6)	0.0311 (5)	0.0095 (5)	0.0081 (5)	−0.0018 (4)
C7	0.0277 (5)	0.0277 (5)	0.0292 (5)	0.0063 (4)	0.0042 (4)	−0.0033 (4)
C8	0.0310 (5)	0.0350 (5)	0.0332 (5)	0.0091 (4)	0.0075 (4)	0.0035 (4)
C9	0.0384 (6)	0.0440 (6)	0.0402 (6)	0.0055 (5)	0.0052 (5)	0.0126 (5)
C10	0.0476 (7)	0.0665 (9)	0.0422 (7)	0.0082 (6)	−0.0013 (6)	0.0063 (6)
C11	0.0316 (5)	0.0335 (5)	0.0326 (5)	0.0104 (4)	0.0040 (4)	0.0004 (4)
C12	0.0307 (5)	0.0282 (5)	0.0294 (5)	0.0071 (4)	0.0065 (4)	0.0028 (4)
C13	0.0304 (5)	0.0332 (5)	0.0332 (5)	0.0096 (4)	0.0033 (4)	0.0024 (4)
C14	0.0354 (5)	0.0314 (5)	0.0345 (5)	0.0128 (4)	0.0099 (4)	0.0057 (4)
C15	0.0400 (6)	0.0260 (5)	0.0285 (5)	0.0068 (4)	0.0089 (4)	0.0025 (4)
C16	0.0314 (5)	0.0375 (6)	0.0395 (6)	0.0054 (4)	0.0012 (4)	−0.0040 (5)
C17	0.0292 (5)	0.0366 (5)	0.0397 (6)	0.0095 (4)	0.0057 (4)	−0.0018 (4)

O1—C4	1.2155 (16)	C5—H5	1.0000
O2—C11	1.3306 (13)	C6—H6A	0.9900
O2—C7	1.4573 (11)	C6—H6B	0.9900
O3—C9	1.4029 (14)	C7—C8	1.5100 (15)
O3—C8	1.4249 (13)	C7—H7	1.0000
O4—C9	1.3962 (14)	C8—H8A	0.9900
O4—C10	1.4262 (18)	C8—H8B	0.9900
O5—C11	1.1978 (14)	C9—H9A	0.9900
O6—N	1.2194 (14)	C9—H9B	0.9900
O7—N	1.2222 (14)	C10—H10A	0.9800
N—C15	1.4771 (13)	C10—H10B	0.9800
C1—C6	1.4880 (14)	C10—H10C	0.9800
C1—C7	1.4991 (15)	C11—C12	1.5005 (14)
C1—C5	1.5223 (15)	C12—C17	1.3905 (15)
C1—C2	1.5301 (15)	C12—C13	1.3936 (15)
C2—C3	1.5395 (18)	C13—C14	1.3909 (15)
C2—H2A	0.9900	C13—H13	0.9500
C2—H2B	0.9900	C14—C15	1.3799 (15)
C3—C4	1.5194 (17)	C14—H14	0.9500
C3—H3A	0.9900	C15—C16	1.3796 (16)
C3—H3B	0.9900	C16—C17	1.3870 (15)
C4—C5	1.4746 (16)	C16—H16	0.9500
C5—C6	1.5271 (16)	C17—H17	0.9500
C11—O2—C7	118.68 (8)	O2—C7—H7	109.6
C9—O3—C8	113.65 (9)	C1—C7—H7	109.6
C9—O4—C10	112.74 (10)	C8—C7—H7	109.6
O6—N—O7	124.19 (10)	O3—C8—C7	106.79 (8)
O6—N—C15	117.96 (10)	O3—C8—H8A	110.4
O7—N—C15	117.85 (10)	C7—C8—H8A	110.4
C6—C1—C7	117.45 (9)	O3—C8—H8B	110.4
C6—C1—C5	60.96 (7)	C7—C8—H8B	110.4
C7—C1—C5	118.28 (9)	H8A—C8—H8B	108.6
C6—C1—C2	116.10 (9)	O4—C9—O3	113.68 (10)
C7—C1—C2	120.97 (9)	O4—C9—H9A	108.8
C5—C1—C2	108.03 (9)	O3—C9—H9A	108.8
C1—C2—C3	105.52 (9)	O4—C9—H9B	108.8
C1—C2—H2A	110.6	O3—C9—H9B	108.8
C3—C2—H2A	110.6	H9A—C9—H9B	107.7
C1—C2—H2B	110.6	O4—C10—H10A	109.5
C3—C2—H2B	110.6	O4—C10—H10B	109.5
H2A—C2—H2B	108.8	H10A—C10—H10B	109.5
C4—C3—C2	105.68 (9)	O4—C10—H10C	109.5
C4—C3—H3A	110.6	H10A—C10—H10C	109.5
C2—C3—H3A	110.6	H10B—C10—H10C	109.5
C4—C3—H3B	110.6	O5—C11—O2	125.11 (10)
C2—C3—H3B	110.6	O5—C11—C12	124.22 (10)
H3A—C3—H3B	108.7	O2—C11—C12	110.68 (9)
O1—C4—C5	125.17 (11)	C17—C12—C13	120.31 (10)
O1—C4—C3	125.78 (11)	C17—C12—C11	121.15 (9)
C5—C4—C3	108.97 (10)	C13—C12—C11	118.53 (9)
C4—C5—C1	107.41 (9)	C14—C13—C12	120.05 (10)
C4—C5—C6	115.41 (10)	C14—C13—H13	120.0
C1—C5—C6	58.41 (7)	C12—C13—H13	120.0
C4—C5—H5	119.9	C15—C14—C13	118.12 (10)
C1—C5—H5	119.9	C15—C14—H14	120.9
C6—C5—H5	119.9	C13—C14—H14	120.9
C1—C6—C5	60.63 (7)	C16—C15—C14	123.09 (10)
C1—C6—H6A	117.7	C16—C15—N	118.07 (10)
C5—C6—H6A	117.7	C14—C15—N	118.84 (10)
C1—C6—H6B	117.7	C15—C16—C17	118.32 (10)
C5—C6—H6B	117.7	C15—C16—H16	120.8
H6A—C6—H6B	114.8	C17—C16—H16	120.8
O2—C7—C1	108.39 (8)	C16—C17—C12	120.11 (10)
O2—C7—C8	106.47 (8)	C16—C17—H17	119.9
C1—C7—C8	113.09 (8)	C12—C17—H17	119.9
C6—C1—C2—C3	−52.63 (13)	C9—O3—C8—C7	178.58 (9)
C7—C1—C2—C3	154.16 (10)	O2—C7—C8—O3	−62.70 (10)
C5—C1—C2—C3	13.23 (12)	C1—C7—C8—O3	178.37 (8)
C1—C2—C3—C4	−20.30 (13)	C10—O4—C9—O3	−63.98 (14)
C2—C3—C4—O1	−156.31 (13)	C8—O3—C9—O4	−60.59 (13)
C2—C3—C4—C5	20.54 (14)	C7—O2—C11—O5	6.45 (18)
O1—C4—C5—C1	164.54 (12)	C7—O2—C11—C12	−173.72 (8)
C3—C4—C5—C1	−12.34 (13)	O5—C11—C12—C17	179.13 (13)
O1—C4—C5—C6	−132.77 (13)	O2—C11—C12—C17	−0.71 (15)
C3—C4—C5—C6	50.36 (13)	O5—C11—C12—C13	−1.43 (19)
C6—C1—C5—C4	109.58 (11)	O2—C11—C12—C13	178.73 (9)
C7—C1—C5—C4	−142.96 (10)	C17—C12—C13—C14	0.32 (17)
C2—C1—C5—C4	−0.81 (12)	C11—C12—C13—C14	−179.12 (10)
C7—C1—C5—C6	107.46 (10)	C12—C13—C14—C15	−0.23 (16)
C2—C1—C5—C6	−110.39 (10)	C13—C14—C15—C16	−0.01 (17)
C7—C1—C6—C5	−108.79 (10)	C13—C14—C15—N	179.31 (10)
C2—C1—C6—C5	97.02 (11)	O6—N—C15—C16	−173.37 (11)
C4—C5—C6—C1	−95.56 (11)	O7—N—C15—C16	6.64 (16)
C11—O2—C7—C1	−120.22 (10)	O6—N—C15—C14	7.28 (16)
C11—O2—C7—C8	117.82 (10)	O7—N—C15—C14	−172.71 (11)
C6—C1—C7—O2	155.15 (9)	C14—C15—C16—C17	0.16 (18)
C5—C1—C7—O2	85.13 (11)	N—C15—C16—C17	−179.17 (10)
C2—C1—C7—O2	−51.99 (12)	C15—C16—C17—C12	−0.07 (18)
C6—C1—C7—C8	−87.05 (11)	C13—C12—C17—C16	−0.17 (18)
C5—C1—C7—C8	−157.06 (9)	C11—C12—C17—C16	179.26 (11)
C2—C1—C7—C8	65.82 (12)