(3R,4S)-3,4-Isopropyl-idenedioxy-3,4-dihydro-2H-pyrrole 1-oxide.

The title compound C(7)H(11)NO(3) was prepared by intra-molecular nucleophilic displacement of 2,3-O-iso-propyl-idene-d-erythronolactol. There are two mol-ecules in the asymmetric unit, which are related by a pseudo-inversion centre. The crystal structure determination confirms unequivocally the configuration of the chiral centres as 3S,4R. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules (into infinite zigzag chains along the a axis.

Related literature

Nitro­nes play a useful role in the synthesis of complex mol­ec­ular frameworks, undergoing several synthetically useful reactions such as 1,3-dipolar cyclo­additions (Tufariello, 1984 ▶) and nucleophilic addition (Merino et al., 2000 ▶; Lombardo & Trombini, 2002 ▶). They also allow direct access to nitro­nes by simple reactions, see: Döpp & Döpp (1990 ▶); Hamer & Macaluso (1964 ▶). For the use of the title compound as a starting material in the sythesis of potential therapeutic (anti­biotic, anti­viral, anti­tumoral) agents, see: Hall et al. (1997 ▶); Closa & Wightman (1998 ▶); McCaig et al. (1998 ▶); Cicchi et al. (2002 ▶); Revuelta et al. (2007 ▶). For a related structure, see: Keleşoğlu et al. (2010 ▶). For the preparation of the title compound, see: Flores et al. (2010 ▶); Cicchi et al. (2006 ▶).

Experimental

Crystal data

C7H11NO3

M = 157.17

Monoclinic,

a = 11.335 (2) Å

b = 5.4467 (11) Å

c = 26.508 (5) Å

β = 101.40 (3)°

V = 1604.2 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.86 mm−1

T = 298 K

0.15 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.902, T max = 0.934

4369 measured reflections

2365 independent reflections

2261 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.05

2365 reflections

204 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack (1983 ▶), 761 Friedel pairs

Flack parameter: 0.0 (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: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013055/bt5507sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013055/bt5507Isup2.hkl

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

C7H11NO3	F(000) = 672
Mr = 157.17	Dx = 1.302 Mg m−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: C 2y	Cell parameters from 2365 reflections
a = 11.335 (2) Å	θ = 1.7–66.9°
b = 5.4467 (11) Å	µ = 0.86 mm−1
c = 26.508 (5) Å	T = 298 K
β = 101.40 (3)°	Prismatic, colourless
V = 1604.2 (6) Å3	0.15 × 0.10 × 0.08 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	2365 independent reflections
Radiation source: fine-focus sealed tube	2261 reflections with I > 2σ(I)
graphite	Rint = 0.022
phi and ω scans	θmax = 66.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→11
Tmin = 0.902, Tmax = 0.934	k = −6→5
4369 measured reflections	l = −28→31

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.4187P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.16 e Å−3
2365 reflections	Δρmin = −0.11 e Å−3
204 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.00105 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 761 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.0 (2)

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'	0.30975 (12)	0.5460 (3)	0.84350 (5)	0.0571 (4)
O2'	0.44334 (11)	0.8279 (3)	0.88116 (5)	0.0566 (4)
O3'	0.14788 (12)	0.7976 (4)	0.96810 (6)	0.0693 (5)
N1'	0.23631 (12)	0.7223 (3)	0.94785 (5)	0.0481 (4)
C1'	0.33483 (16)	0.4762 (4)	0.89604 (7)	0.0476 (4)
H1'	0.3729	0.3142	0.9013	0.057*
C3'	0.34095 (15)	0.8196 (4)	0.95186 (6)	0.0464 (4)
H3'	0.3657	0.9601	0.9709	0.056*
C4'	0.41764 (14)	0.6811 (4)	0.92243 (6)	0.0463 (4)
H4'	0.4907	0.6168	0.9445	0.056*
C5'	0.40764 (17)	0.6940 (4)	0.83486 (7)	0.0525 (5)
C6'	0.3627 (3)	0.8714 (6)	0.79227 (9)	0.0866 (8)
H6'1	0.2985	0.9674	0.8009	0.130*
H6'2	0.3337	0.7826	0.7610	0.130*
H6'3	0.4271	0.9780	0.7876	0.130*
C7'	0.5109 (3)	0.5377 (6)	0.82529 (12)	0.0928 (9)
H7'1	0.4860	0.4458	0.7941	0.139*
H7'2	0.5349	0.4266	0.8536	0.139*
H7'3	0.5776	0.6413	0.8221	0.139*
C2'	0.22244 (16)	0.4919 (4)	0.91839 (8)	0.0553 (5)
H2'1	0.1510	0.4965	0.8913	0.066*
H2'2	0.2168	0.3528	0.9406	0.066*
O1	0.09613 (11)	0.3663 (3)	0.62016 (5)	0.0557 (4)
O2	0.21761 (13)	0.6589 (3)	0.66182 (5)	0.0666 (5)
O3	0.36792 (14)	0.3733 (4)	0.52993 (7)	0.0861 (6)
N1	0.29356 (13)	0.4731 (4)	0.55436 (6)	0.0544 (4)
C1	0.10961 (15)	0.5348 (4)	0.58059 (7)	0.0514 (5)
H1	0.0341	0.6186	0.5659	0.062*
C2	0.16439 (16)	0.4088 (4)	0.54033 (7)	0.0556 (5)
H2A	0.1530	0.2325	0.5413	0.067*
H2B	0.1293	0.4687	0.5062	0.067*
C3	0.31507 (17)	0.6385 (4)	0.58935 (8)	0.0586 (5)
H3	0.3910	0.7049	0.6014	0.070*
C4	0.20620 (17)	0.7127 (4)	0.60855 (7)	0.0522 (5)
H4	0.1847	0.8848	0.6007	0.063*
C5	0.12362 (18)	0.4967 (4)	0.66756 (7)	0.0558 (5)
C6	0.0151 (3)	0.6365 (7)	0.67681 (11)	0.0971 (10)
H6A	−0.0464	0.5228	0.6816	0.146*
H6B	−0.0148	0.7394	0.6477	0.146*
H6C	0.0374	0.7365	0.7070	0.146*
C7	0.1714 (3)	0.3142 (6)	0.70956 (9)	0.0882 (8)
H7A	0.2404	0.2320	0.7016	0.132*
H7B	0.1101	0.1958	0.7120	0.132*
H7C	0.1942	0.3990	0.7418	0.132*

	U11	U22	U33	U12	U13	U23
O1'	0.0642 (8)	0.0626 (10)	0.0440 (7)	−0.0248 (7)	0.0098 (6)	−0.0060 (6)
O2'	0.0573 (7)	0.0637 (9)	0.0517 (7)	−0.0225 (7)	0.0178 (6)	−0.0098 (7)
O3'	0.0556 (7)	0.0876 (12)	0.0713 (9)	0.0236 (8)	0.0283 (7)	0.0071 (9)
N1'	0.0431 (7)	0.0554 (10)	0.0467 (8)	0.0091 (7)	0.0108 (6)	0.0067 (7)
C1'	0.0541 (9)	0.0433 (10)	0.0471 (9)	0.0010 (9)	0.0142 (8)	0.0032 (8)
C3'	0.0484 (9)	0.0476 (10)	0.0420 (9)	−0.0002 (8)	0.0061 (7)	0.0000 (8)
C4'	0.0374 (8)	0.0565 (12)	0.0434 (9)	0.0022 (8)	0.0042 (7)	0.0000 (9)
C5'	0.0612 (11)	0.0527 (12)	0.0467 (10)	−0.0157 (9)	0.0176 (8)	−0.0056 (9)
C6'	0.115 (2)	0.0827 (19)	0.0616 (13)	−0.0206 (17)	0.0163 (13)	0.0152 (14)
C7'	0.1036 (19)	0.084 (2)	0.108 (2)	0.0040 (17)	0.0634 (17)	−0.0118 (18)
C2'	0.0509 (10)	0.0578 (12)	0.0581 (11)	−0.0114 (10)	0.0127 (8)	−0.0032 (10)
O1	0.0564 (7)	0.0588 (9)	0.0530 (7)	−0.0180 (7)	0.0137 (6)	−0.0052 (7)
O2	0.0758 (9)	0.0742 (12)	0.0499 (8)	−0.0306 (9)	0.0126 (6)	−0.0074 (8)
O3	0.0679 (9)	0.1030 (15)	0.0940 (11)	0.0252 (10)	0.0316 (8)	−0.0034 (12)
N1	0.0472 (8)	0.0598 (10)	0.0560 (9)	0.0068 (8)	0.0098 (7)	0.0045 (9)
C1	0.0395 (8)	0.0617 (14)	0.0502 (10)	0.0022 (9)	0.0022 (7)	0.0044 (9)
C2	0.0511 (10)	0.0646 (14)	0.0488 (10)	−0.0048 (9)	0.0045 (8)	−0.0025 (10)
C3	0.0465 (9)	0.0662 (14)	0.0612 (11)	−0.0129 (9)	0.0061 (8)	0.0058 (11)
C4	0.0600 (11)	0.0397 (10)	0.0572 (11)	−0.0048 (9)	0.0127 (9)	0.0008 (9)
C5	0.0627 (11)	0.0549 (12)	0.0523 (10)	−0.0128 (10)	0.0179 (8)	−0.0059 (10)
C6	0.0920 (19)	0.112 (3)	0.098 (2)	0.0096 (19)	0.0441 (16)	−0.018 (2)
C7	0.127 (2)	0.0758 (18)	0.0603 (13)	−0.0100 (18)	0.0159 (13)	0.0090 (14)

O1'—C1'	1.417 (2)	O1—C5	1.423 (2)
O1'—C5'	1.426 (2)	O1—C1	1.425 (2)
O2'—C5'	1.416 (2)	O2—C5	1.415 (2)
O2'—C4'	1.431 (2)	O2—C4	1.423 (2)
O3'—N1'	1.2937 (19)	O3—N1	1.281 (2)
N1'—C3'	1.284 (2)	N1—C3	1.282 (3)
N1'—C2'	1.470 (3)	N1—C2	1.480 (2)
C1'—C2'	1.510 (2)	C1—C2	1.502 (3)
C1'—C4'	1.535 (3)	C1—C4	1.538 (3)
C1'—H1'	0.9800	C1—H1	0.9800
C3'—C4'	1.484 (3)	C2—H2A	0.9700
C3'—H3'	0.9300	C2—H2B	0.9700
C4'—H4'	0.9800	C3—C4	1.481 (3)
C5'—C6'	1.497 (3)	C3—H3	0.9300
C5'—C7'	1.509 (4)	C4—H4	0.9800
C6'—H6'1	0.9600	C5—C6	1.507 (3)
C6'—H6'2	0.9600	C5—C7	1.511 (4)
C6'—H6'3	0.9600	C6—H6A	0.9600
C7'—H7'1	0.9600	C6—H6B	0.9600
C7'—H7'2	0.9600	C6—H6C	0.9600
C7'—H7'3	0.9600	C7—H7A	0.9600
C2'—H2'1	0.9700	C7—H7B	0.9600
C2'—H2'2	0.9700	C7—H7C	0.9600
C1'—O1'—C5'	107.35 (14)	C5—O1—C1	106.97 (16)
C5'—O2'—C4'	107.96 (15)	C5—O2—C4	108.22 (15)
C3'—N1'—O3'	127.85 (19)	O3—N1—C3	127.89 (18)
C3'—N1'—C2'	113.34 (15)	O3—N1—C2	119.33 (19)
O3'—N1'—C2'	118.74 (16)	C3—N1—C2	112.67 (16)
O1'—C1'—C2'	110.46 (15)	O1—C1—C2	110.37 (18)
O1'—C1'—C4'	103.80 (15)	O1—C1—C4	102.75 (14)
C2'—C1'—C4'	105.50 (15)	C2—C1—C4	105.98 (15)
O1'—C1'—H1'	112.2	O1—C1—H1	112.4
C2'—C1'—H1'	112.2	C2—C1—H1	112.4
C4'—C1'—H1'	112.2	C4—C1—H1	112.4
N1'—C3'—C4'	111.98 (18)	N1—C2—C1	103.94 (16)
N1'—C3'—H3'	124.0	N1—C2—H2A	111.0
C4'—C3'—H3'	124.0	C1—C2—H2A	111.0
O2'—C4'—C3'	110.31 (17)	N1—C2—H2B	111.0
O2'—C4'—C1'	104.86 (13)	C1—C2—H2B	111.0
C3'—C4'—C1'	103.90 (14)	H2A—C2—H2B	109.0
O2'—C4'—H4'	112.4	N1—C3—C4	112.86 (17)
C3'—C4'—H4'	112.4	N1—C3—H3	123.6
C1'—C4'—H4'	112.4	C4—C3—H3	123.6
O2'—C5'—O1'	104.48 (13)	O2—C4—C3	111.49 (17)
O2'—C5'—C6'	108.5 (2)	O2—C4—C1	105.37 (15)
O1'—C5'—C6'	109.05 (19)	C3—C4—C1	102.97 (17)
O2'—C5'—C7'	109.8 (2)	O2—C4—H4	112.2
O1'—C5'—C7'	111.2 (2)	C3—C4—H4	112.2
C6'—C5'—C7'	113.4 (2)	C1—C4—H4	112.2
C5'—C6'—H6'1	109.5	O2—C5—O1	104.75 (13)
C5'—C6'—H6'2	109.5	O2—C5—C6	111.0 (2)
H6'1—C6'—H6'2	109.5	O1—C5—C6	110.64 (19)
C5'—C6'—H6'3	109.5	O2—C5—C7	108.8 (2)
H6'1—C6'—H6'3	109.5	O1—C5—C7	107.8 (2)
H6'2—C6'—H6'3	109.5	C6—C5—C7	113.4 (2)
C5'—C7'—H7'1	109.5	C5—C6—H6A	109.5
C5'—C7'—H7'2	109.5	C5—C6—H6B	109.5
H7'1—C7'—H7'2	109.5	H6A—C6—H6B	109.5
C5'—C7'—H7'3	109.5	C5—C6—H6C	109.5
H7'1—C7'—H7'3	109.5	H6A—C6—H6C	109.5
H7'2—C7'—H7'3	109.5	H6B—C6—H6C	109.5
N1'—C2'—C1'	104.30 (16)	C5—C7—H7A	109.5
N1'—C2'—H2'1	110.9	C5—C7—H7B	109.5
C1'—C2'—H2'1	110.9	H7A—C7—H7B	109.5
N1'—C2'—H2'2	110.9	C5—C7—H7C	109.5
C1'—C2'—H2'2	110.9	H7A—C7—H7C	109.5
H2'1—C2'—H2'2	108.9	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.44	3.366 (3)	171
C1—H1···O3ii	0.98	2.38	3.355 (3)	171
C2—H2A···O3iii	0.97	2.70	3.441 (3)	134
C2—H2B···O3iv	0.97	2.41	3.120 (3)	130
C2'—H2'1···O2'v	0.97	2.49	3.247 (2)	135
C4'—H4'···O3'vi	0.98	2.48	3.375 (3)	152
C2'—H2'2···O3'vii	0.97	2.61	3.254 (2)	124
C3'—H3'···O3'viii	0.93	2.48	3.345 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.44	3.366 (3)	171
C1—H1⋯O3ii	0.98	2.38	3.355 (3)	171
C2—H2A⋯O3iii	0.97	2.70	3.441 (3)	134
C2—H2B⋯O3iv	0.97	2.41	3.120 (3)	130
C2′—H2′1⋯O2′v	0.97	2.49	3.247 (2)	135
C4′—H4′⋯O3′vi	0.98	2.48	3.375 (3)	152
C2′—H2′2⋯O3′vii	0.97	2.61	3.254 (2)	124
C3′—H3′⋯O3′viii	0.93	2.48	3.345 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .