2,5-Dioxopyrrolidin-1-yl methane­sulfonate

The title compound, C₅H₇NO₅S, is an ester of methane­sulfonic acid and N-hydroxy­succinimide in which the N atom has a flattened pyramidal geometry. The mol­ecular arrangement is stabilized by C—H...O hydrogen bonds, forming double-layer sheets that are linked via short C=O...C=O carbon­yl–carbonyl inter­actions to generate a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.094
• Data-to-parameter ratio = 36.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O6     ..  C4      ..       2.77 Ang.

Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C3      ..       2.96 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C2      ..       3.01 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP (Bruker, 1999); software used to prepare material for publication: SHELXL97.

2,5-Dioxopyrrolidin-1-yl methanesulfonate

Crystal data

C5H7NO5S	F(000) = 400
Mr = 193.18	Dx = 1.661 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9833 reflections
a = 8.084 (2) Å	θ = 4–37.5°
b = 5.484 (1) Å	µ = 0.40 mm^−1
c = 17.481 (5) Å	T = 100 K
β = 94.52 (3)°	Elongated plate cut from larger crystal, colorless
V = 772.6 (3) Å^3	0.37 × 0.13 × 0.05 mm
Z = 4

Data collection

Kuma KM-4-CCD diffractometer	4063 independent reflections
Radiation source: fine-focus sealed tube	2804 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 37.5°, θmin = 5.0°
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2003)	h = −13→13
Tmin = 0.887, Tmax = 0.981	k = −9→9
17367 measured reflections	l = −29→29

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.048P)^2] where P = (Fo^2 + 2Fc^2)/3
4063 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S	0.22366 (3)	0.60725 (5)	0.442547 (14)	0.01303 (7)
O1	0.33402 (9)	0.69795 (14)	0.37274 (4)	0.01328 (14)
O2	0.05283 (9)	0.65467 (16)	0.42119 (5)	0.01863 (17)
O3	0.30756 (10)	0.72952 (15)	0.50605 (4)	0.01998 (17)
O5	0.13058 (9)	0.99241 (14)	0.27536 (5)	0.01780 (16)
O6	0.45084 (9)	0.31163 (15)	0.29086 (5)	0.01796 (16)
N1	0.26848 (10)	0.62967 (15)	0.29969 (5)	0.01153 (16)
C1	0.18508 (12)	0.80410 (19)	0.25218 (6)	0.01231 (18)
C2	0.18618 (12)	0.7078 (2)	0.17213 (6)	0.01461 (19)
H2B	0.2463	0.8208	0.1399	0.018*
H2A	0.0714	0.6880	0.1488	0.018*
C3	0.27468 (13)	0.4600 (2)	0.17878 (6)	0.01490 (19)
H3B	0.1949	0.3252	0.1677	0.018*
H3A	0.3625	0.4500	0.1425	0.018*
C4	0.34866 (12)	0.44699 (18)	0.26048 (6)	0.01247 (18)
C11	0.26079 (14)	0.2937 (2)	0.44771 (6)	0.0174 (2)
H111	0.1983	0.2225	0.4880	0.026*
H112	0.3796	0.2645	0.4597	0.026*
H113	0.2253	0.2182	0.3983	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01437 (11)	0.01482 (12)	0.01002 (11)	0.00059 (9)	0.00176 (8)	0.00034 (9)
O1	0.0139 (3)	0.0165 (4)	0.0093 (3)	−0.0027 (3)	0.0004 (3)	−0.0011 (3)
O2	0.0142 (3)	0.0245 (4)	0.0176 (4)	0.0034 (3)	0.0041 (3)	0.0039 (3)
O3	0.0266 (4)	0.0215 (4)	0.0116 (4)	−0.0022 (3)	−0.0001 (3)	−0.0036 (3)
O5	0.0191 (4)	0.0143 (4)	0.0204 (4)	0.0037 (3)	0.0042 (3)	0.0020 (3)
O6	0.0153 (3)	0.0187 (4)	0.0199 (4)	0.0053 (3)	0.0017 (3)	0.0015 (3)
N1	0.0120 (3)	0.0144 (4)	0.0081 (3)	0.0014 (3)	0.0000 (3)	−0.0008 (3)
C1	0.0100 (4)	0.0138 (4)	0.0133 (4)	−0.0014 (3)	0.0017 (3)	0.0037 (4)
C2	0.0136 (4)	0.0194 (5)	0.0108 (4)	0.0009 (4)	0.0013 (3)	0.0030 (4)
C3	0.0149 (4)	0.0184 (5)	0.0116 (4)	−0.0009 (4)	0.0020 (3)	−0.0012 (4)
C4	0.0107 (4)	0.0138 (4)	0.0133 (4)	−0.0007 (3)	0.0038 (3)	−0.0007 (4)
C11	0.0195 (5)	0.0154 (5)	0.0171 (5)	0.0008 (4)	0.0014 (4)	0.0026 (4)

Geometric parameters (Å, º)

S—O3	1.4225 (9)	C2—C3	1.5359 (15)
S—O2	1.4258 (9)	C2—H2B	0.9900
S—O1	1.6445 (9)	C2—H2A	0.9900
S—C11	1.7467 (12)	C3—C4	1.5059 (15)
O1—N1	1.3946 (11)	C3—H3B	0.9900
O5—C1	1.2053 (13)	C3—H3A	0.9900
O6—C4	1.2027 (12)	C11—H111	0.9800
N1—C4	1.4013 (13)	C11—H112	0.9800
N1—C1	1.4039 (13)	C11—H113	0.9800
C1—C2	1.4964 (15)
O3—S—O2	120.72 (5)	C3—C2—H2A	110.5
O3—S—O1	100.57 (5)	H2B—C2—H2A	108.7
O2—S—O1	108.75 (5)	C4—C3—C2	105.16 (8)
O3—S—C11	110.75 (5)	C4—C3—H3B	110.7
O2—S—C11	110.61 (5)	C2—C3—H3B	110.7
O1—S—C11	103.60 (5)	C4—C3—H3A	110.7
N1—O1—S	114.15 (6)	C2—C3—H3A	110.7
O1—N1—C4	118.87 (8)	H3B—C3—H3A	108.8
O1—N1—C1	119.26 (8)	O6—C4—N1	123.59 (10)
C4—N1—C1	114.64 (9)	O6—C4—C3	130.98 (10)
O5—C1—N1	123.79 (10)	N1—C4—C3	105.40 (8)
O5—C1—C2	130.24 (10)	S—C11—H111	109.5
N1—C1—C2	105.95 (9)	S—C11—H112	109.5
C1—C2—C3	106.18 (8)	H111—C11—H112	109.5
C1—C2—H2B	110.5	S—C11—H113	109.5
C3—C2—H2B	110.5	H111—C11—H113	109.5
C1—C2—H2A	110.5	H112—C11—H113	109.5
O3—S—O1—N1	−172.59 (6)	O5—C1—C2—C3	179.38 (10)
O2—S—O1—N1	−44.85 (8)	N1—C1—C2—C3	1.17 (10)
C11—S—O1—N1	72.83 (7)	C1—C2—C3—C4	−10.38 (10)
S—O1—N1—C4	−108.09 (8)	O1—N1—C4—O6	15.18 (14)
S—O1—N1—C1	103.20 (9)	C1—N1—C4—O6	165.27 (10)
O1—N1—C1—O5	−18.63 (14)	O1—N1—C4—C3	−166.59 (8)
C4—N1—C1—O5	−168.60 (10)	C1—N1—C4—C3	−16.49 (11)
O1—N1—C1—C2	159.73 (8)	C2—C3—C4—O6	−166.21 (11)
C4—N1—C1—C2	9.76 (11)	C2—C3—C4—N1	15.74 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O5^i	0.99	2.43	3.0274 (15)	118
C2—H2B···O3^ii	0.99	2.45	3.1557 (16)	128

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.