Crystal structure of (2R*,3aR*)-2-phenyl­sulfonyl-2,3,3a,4,5,6-hexa­hydro­pyrrolo­[1,2-b]isoxazole

A new isoxazolidine has been obtained by 1,3-dipolar cyclo­addition of a nitrone and phenyl vinyl sulfone

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.109
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.944 Note
PLAT241_ALERT_2_B High   'MainMol' Ueq as Compared to Neighbors of         C1 Check

Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.5 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00418 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           6 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.596        116 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle from 120 Deg for  O1          110.7 Degre
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C6      (Centro SPGR)          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          89 % Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker 2006); cell refinement: SAINT (Bruker 2006); data reduction: SAINT (Bruker 2006); 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: SHELXTL/PC (Sheldrick, 2008).

(2R*,3aR*)-2-Phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole

Crystal data

C12H15NO3S	F(000) = 536
Mr = 253.31	Dx = 1.361 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1548 reflections
a = 12.5730 (4) Å	θ = 8.7–66.1°
b = 5.4443 (2) Å	µ = 2.31 mm^−1
c = 18.2266 (6) Å	T = 298 K
β = 97.754 (2)°	Prismatic, colorless
V = 1236.22 (7) Å^3	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker APEXII CCD area detector diffractometer	2074 independent reflections
Radiation source: fine-focus sealed tube	1949 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
phi and ω scans	θmax = 66.8°, θmin = 8.5°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −14→13
Tmin = 0.603, Tmax = 0.794	k = −6→6
9571 measured reflections	l = −17→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.5869P] where P = (Fo^2 + 2Fc^2)/3
2074 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.18509 (4)	0.20282 (9)	0.19580 (3)	0.0506 (2)
O1	0.27595 (12)	0.0779 (4)	0.33002 (8)	0.0780 (5)
O2	0.10289 (12)	0.0979 (4)	0.14263 (9)	0.0745 (5)
O3	0.17911 (13)	0.4582 (3)	0.21257 (10)	0.0722 (5)
N1	0.24857 (16)	0.2358 (4)	0.38806 (12)	0.0767 (6)
C1	0.2723 (3)	0.0922 (13)	0.45671 (19)	0.173 (3)
H1A	0.3095	−0.0579	0.4469	0.207*
H1B	0.3185	0.1863	0.4933	0.207*
C2	0.1731 (3)	0.0332 (7)	0.48481 (17)	0.1044 (11)
H2A	0.1821	0.0422	0.5384	0.125*
H2B	0.1487	−0.1303	0.4696	0.125*
C3	0.0964 (3)	0.2227 (6)	0.45154 (17)	0.0932 (9)
H3A	0.1018	0.3717	0.4810	0.112*
H3B	0.0231	0.1629	0.4466	0.112*
C4	0.13178 (19)	0.2665 (5)	0.37671 (14)	0.0653 (6)
H4	0.1134	0.4343	0.3602	0.078*
C5	0.08854 (17)	0.0856 (5)	0.31715 (13)	0.0669 (6)
H5A	0.0605	−0.0600	0.3385	0.080*
H5B	0.0322	0.1592	0.2824	0.080*
C6	0.18549 (16)	0.0244 (4)	0.27984 (11)	0.0548 (5)
H6	0.1848	−0.1510	0.2677	0.066*
C7	0.31162 (15)	0.1448 (4)	0.16793 (11)	0.0489 (5)
C8	0.3261 (2)	−0.0590 (5)	0.12636 (15)	0.0748 (7)
H8	0.2699	−0.1680	0.1129	0.090*
C9	0.4260 (3)	−0.0996 (6)	0.10473 (19)	0.0949 (9)
H9	0.4371	−0.2375	0.0766	0.114*
C10	0.5086 (2)	0.0610 (7)	0.12436 (18)	0.0902 (9)
H10	0.5754	0.0320	0.1095	0.108*
C11	0.4932 (2)	0.2622 (6)	0.16530 (18)	0.0843 (8)
H11	0.5495	0.3712	0.1783	0.101*
C12	0.39431 (18)	0.3066 (4)	0.18785 (14)	0.0650 (6)
H12	0.3839	0.4444	0.2162	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0409 (3)	0.0501 (3)	0.0601 (3)	−0.00016 (19)	0.0047 (2)	0.0026 (2)
O1	0.0465 (8)	0.1268 (15)	0.0598 (9)	0.0238 (9)	0.0034 (7)	−0.0082 (10)
O2	0.0485 (8)	0.1031 (13)	0.0677 (9)	−0.0149 (8)	−0.0079 (7)	0.0020 (9)
O3	0.0706 (10)	0.0466 (8)	0.1034 (12)	0.0115 (7)	0.0265 (9)	0.0072 (8)
N1	0.0565 (12)	0.0980 (16)	0.0779 (13)	−0.0213 (11)	0.0169 (10)	−0.0249 (12)
C1	0.102 (3)	0.350 (8)	0.0652 (18)	0.079 (4)	0.0086 (18)	0.015 (3)
C2	0.146 (3)	0.098 (2)	0.0722 (17)	0.015 (2)	0.0272 (19)	0.0106 (16)
C3	0.094 (2)	0.111 (2)	0.0831 (18)	0.0098 (18)	0.0415 (17)	0.0043 (17)
C4	0.0646 (14)	0.0611 (13)	0.0743 (14)	0.0105 (11)	0.0250 (11)	0.0033 (11)
C5	0.0437 (11)	0.0849 (16)	0.0728 (14)	−0.0104 (11)	0.0101 (10)	0.0128 (12)
C6	0.0541 (11)	0.0495 (11)	0.0603 (12)	−0.0008 (9)	0.0062 (9)	−0.0008 (9)
C7	0.0446 (10)	0.0478 (11)	0.0539 (10)	−0.0008 (8)	0.0054 (8)	0.0021 (9)
C8	0.0772 (16)	0.0601 (14)	0.0901 (17)	−0.0040 (12)	0.0223 (13)	−0.0145 (13)
C9	0.104 (2)	0.0832 (19)	0.105 (2)	0.0252 (18)	0.0439 (18)	−0.0077 (17)
C10	0.0640 (16)	0.108 (2)	0.105 (2)	0.0248 (16)	0.0352 (15)	0.0315 (19)
C11	0.0447 (13)	0.100 (2)	0.108 (2)	−0.0088 (13)	0.0087 (13)	0.0152 (17)
C12	0.0512 (12)	0.0650 (14)	0.0782 (15)	−0.0091 (10)	0.0064 (11)	−0.0057 (11)

Geometric parameters (Å, º)

S1—O3	1.4277 (16)	C4—C5	1.511 (4)
S1—O2	1.4364 (16)	C4—H4	0.9800
S1—C7	1.763 (2)	C5—C6	1.511 (3)
S1—C6	1.813 (2)	C5—H5A	0.9700
O1—C6	1.391 (3)	C5—H5B	0.9700
O1—N1	1.440 (3)	C6—H6	0.9800
N1—C4	1.465 (3)	C7—C8	1.370 (3)
N1—C1	1.472 (5)	C7—C12	1.374 (3)
C1—C2	1.446 (5)	C8—C9	1.384 (4)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—C10	1.367 (5)
C2—C3	1.485 (4)	C9—H9	0.9300
C2—H2A	0.9700	C10—C11	1.354 (5)
C2—H2B	0.9700	C10—H10	0.9300
C3—C4	1.510 (4)	C11—C12	1.382 (4)
C3—H3A	0.9700	C11—H11	0.9300
C3—H3B	0.9700	C12—H12	0.9300
O3—S1—O2	118.54 (11)	C3—C4—H4	109.8
O3—S1—C7	108.17 (9)	C5—C4—H4	109.8
O2—S1—C7	109.24 (10)	C6—C5—C4	103.48 (17)
O3—S1—C6	109.58 (10)	C6—C5—H5A	111.1
O2—S1—C6	106.06 (10)	C4—C5—H5A	111.1
C7—S1—C6	104.34 (9)	C6—C5—H5B	111.1
C6—O1—N1	110.65 (15)	C4—C5—H5B	111.1
O1—N1—C4	107.39 (17)	H5A—C5—H5B	109.0
O1—N1—C1	105.4 (3)	O1—C6—C5	107.19 (17)
C4—N1—C1	105.4 (2)	O1—C6—S1	110.63 (15)
C2—C1—N1	109.5 (3)	C5—C6—S1	110.59 (15)
C2—C1—H1A	109.8	O1—C6—H6	109.5
N1—C1—H1A	109.8	C5—C6—H6	109.5
C2—C1—H1B	109.8	S1—C6—H6	109.5
N1—C1—H1B	109.8	C8—C7—C12	120.9 (2)
H1A—C1—H1B	108.2	C8—C7—S1	119.84 (17)
C1—C2—C3	104.2 (3)	C12—C7—S1	119.31 (16)
C1—C2—H2A	110.9	C7—C8—C9	118.8 (3)
C3—C2—H2A	110.9	C7—C8—H8	120.6
C1—C2—H2B	110.9	C9—C8—H8	120.6
C3—C2—H2B	110.9	C10—C9—C8	120.6 (3)
H2A—C2—H2B	108.9	C10—C9—H9	119.7
C2—C3—C4	103.0 (2)	C8—C9—H9	119.7
C2—C3—H3A	111.2	C11—C10—C9	120.1 (2)
C4—C3—H3A	111.2	C11—C10—H10	119.9
C2—C3—H3B	111.2	C9—C10—H10	119.9
C4—C3—H3B	111.2	C10—C11—C12	120.4 (3)
H3A—C3—H3B	109.1	C10—C11—H11	119.8
N1—C4—C3	105.5 (2)	C12—C11—H11	119.8
N1—C4—C5	106.48 (18)	C7—C12—C11	119.2 (2)
C3—C4—C5	115.1 (2)	C7—C12—H12	120.4
N1—C4—H4	109.8	C11—C12—H12	120.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3^i	0.98	2.35	3.314 (3)	168
C11—H11···O1^ii	0.93	2.49	3.364 (3)	157

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