1-[(4-Methyl­phen­yl)sulfon­yl]pyrrolidin-2-one

The title mol­ecular structure, C₁₁H₁₃NO₃S, contains a five-membered ring which adopts an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.094
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

1-[(4-Methylphenyl)sulfonyl]pyrrolidin-2-one

Crystal data

C11H13NO3S	F(000) = 504
Mr = 239.28	Dx = 1.408 Mg m^−3
Monoclinic, P21/n	Melting point = 420–422 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.144 (5) Å	Cell parameters from 3329 reflections
b = 13.717 (10) Å	θ = 3.6–26.0°
c = 10.644 (8) Å	µ = 0.28 mm^−1
β = 108.27 (3)°	T = 173 K
V = 1129.1 (14) Å^3	Block, colorless
Z = 4	0.18 × 0.16 × 0.06 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	2190 independent reflections
Radiation source: fine-focus sealed tube	1914 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 3.6°
Absorption correction: multi-scan SORTAV (Blessing, 1997)	h = −10→10
Tmin = 0.952, Tmax = 0.984	k = −12→16
3329 measured reflections	l = −13→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.606P] where P = (Fo^2 + 2Fc^2)/3
2190 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.35091 (5)	0.33271 (3)	0.05541 (4)	0.02759 (15)
O1	0.40634 (16)	0.36917 (10)	0.18795 (12)	0.0377 (3)
O2	0.19813 (15)	0.37126 (9)	−0.03746 (12)	0.0343 (3)
O3	0.38883 (19)	0.30587 (11)	−0.21630 (13)	0.0462 (4)
N1	0.51676 (18)	0.35375 (11)	−0.00009 (15)	0.0311 (3)
C1	0.3356 (2)	0.20536 (13)	0.05888 (15)	0.0274 (4)
C2	0.2003 (2)	0.15799 (14)	−0.03321 (17)	0.0344 (4)
H2	0.1154	0.1940	−0.0984	0.041*
C3	0.1908 (2)	0.05757 (14)	−0.02874 (18)	0.0383 (4)
H3	0.0984	0.0247	−0.0917	0.046*
C4	0.3138 (2)	0.00343 (13)	0.06624 (17)	0.0333 (4)
C5	0.4478 (2)	0.05316 (14)	0.15703 (17)	0.0349 (4)
H5	0.5324	0.0173	0.2226	0.042*
C6	0.4613 (2)	0.15355 (13)	0.15436 (17)	0.0318 (4)
H6	0.5544	0.1865	0.2165	0.038*
C7	0.3010 (3)	−0.10565 (14)	0.0712 (2)	0.0453 (5)
H7A	0.3980	−0.1310	0.1439	0.068*	0.50
H7B	0.3047	−0.1334	−0.0127	0.068*	0.50
H7C	0.1918	−0.1237	0.0856	0.068*	0.50
H7D	0.1984	−0.1277	0.0006	0.068*	0.50
H7E	0.2916	−0.1253	0.1572	0.068*	0.50
H7F	0.4045	−0.1351	0.0589	0.068*	0.50
C8	0.5110 (2)	0.33898 (13)	−0.13078 (19)	0.0358 (4)
C9	0.6838 (3)	0.37194 (17)	−0.1394 (2)	0.0533 (6)
H9A	0.6743	0.4375	−0.1801	0.064*
H9B	0.7273	0.3257	−0.1931	0.064*
C10	0.8037 (3)	0.37437 (16)	0.0022 (3)	0.0534 (6)
H10A	0.8878	0.4285	0.0147	0.064*
H10B	0.8680	0.3122	0.0253	0.064*
C11	0.6861 (2)	0.38967 (14)	0.0869 (2)	0.0404 (5)
H11A	0.7262	0.3514	0.1698	0.048*
H11B	0.6799	0.4594	0.1089	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0243 (2)	0.0333 (2)	0.0260 (2)	0.00092 (16)	0.00913 (16)	0.00000 (16)
O1	0.0410 (7)	0.0430 (7)	0.0294 (7)	−0.0007 (6)	0.0113 (6)	−0.0066 (5)
O2	0.0271 (6)	0.0380 (7)	0.0370 (7)	0.0048 (5)	0.0087 (5)	0.0042 (5)
O3	0.0517 (9)	0.0557 (9)	0.0339 (7)	−0.0009 (7)	0.0171 (7)	−0.0042 (6)
N1	0.0255 (7)	0.0353 (8)	0.0338 (8)	−0.0029 (6)	0.0113 (6)	0.0011 (6)
C1	0.0259 (8)	0.0333 (9)	0.0254 (8)	0.0001 (7)	0.0115 (7)	0.0022 (7)
C2	0.0302 (9)	0.0398 (10)	0.0294 (9)	−0.0026 (7)	0.0039 (7)	0.0056 (7)
C3	0.0372 (10)	0.0416 (10)	0.0336 (9)	−0.0080 (8)	0.0076 (8)	0.0006 (8)
C4	0.0384 (10)	0.0342 (10)	0.0334 (9)	0.0022 (7)	0.0203 (8)	0.0027 (7)
C5	0.0314 (9)	0.0411 (10)	0.0328 (9)	0.0095 (7)	0.0110 (7)	0.0059 (7)
C6	0.0265 (9)	0.0408 (10)	0.0271 (9)	0.0028 (7)	0.0069 (7)	0.0010 (7)
C7	0.0553 (13)	0.0378 (11)	0.0505 (12)	0.0025 (9)	0.0275 (10)	0.0031 (9)
C8	0.0411 (10)	0.0318 (9)	0.0413 (10)	0.0035 (8)	0.0227 (9)	0.0030 (8)
C9	0.0596 (14)	0.0458 (12)	0.0738 (16)	−0.0028 (10)	0.0486 (13)	0.0010 (11)
C10	0.0325 (11)	0.0429 (12)	0.0925 (18)	−0.0042 (9)	0.0305 (11)	−0.0045 (11)
C11	0.0253 (9)	0.0393 (10)	0.0525 (12)	−0.0050 (7)	0.0064 (8)	0.0024 (8)

Geometric parameters (Å, º)

S1—O2	1.4260 (14)	C6—H6	0.9500
S1—O1	1.4300 (16)	C7—H7A	0.9800
S1—N1	1.6604 (17)	C7—H7B	0.9800
S1—C1	1.752 (2)	C7—H7C	0.9800
O3—C8	1.207 (2)	C7—H7D	0.9800
N1—C8	1.392 (3)	C7—H7E	0.9800
N1—C11	1.484 (2)	C7—H7F	0.9800
C1—C2	1.386 (2)	C8—C9	1.508 (3)
C1—C6	1.390 (2)	C9—C10	1.517 (4)
C2—C3	1.381 (3)	C9—H9A	0.9900
C2—H2	0.9500	C9—H9B	0.9900
C3—C4	1.394 (3)	C10—C11	1.521 (3)
C3—H3	0.9500	C10—H10A	0.9900
C4—C5	1.389 (3)	C10—H10B	0.9900
C4—C7	1.502 (3)	C11—H11A	0.9900
C5—C6	1.382 (3)	C11—H11B	0.9900
C5—H5	0.9500
O2—S1—O1	119.42 (9)	H7B—C7—H7D	56.3
O2—S1—N1	108.62 (9)	H7C—C7—H7D	56.3
O1—S1—N1	104.46 (9)	C4—C7—H7E	109.5
O2—S1—C1	109.39 (8)	H7A—C7—H7E	56.3
O1—S1—C1	109.29 (8)	H7B—C7—H7E	141.1
N1—S1—C1	104.58 (7)	H7C—C7—H7E	56.3
C8—N1—C11	113.92 (15)	H7D—C7—H7E	109.5
C8—N1—S1	123.63 (13)	C4—C7—H7F	109.5
C11—N1—S1	122.45 (13)	H7A—C7—H7F	56.3
C2—C1—C6	121.15 (17)	H7B—C7—H7F	56.3
C2—C1—S1	119.89 (13)	H7C—C7—H7F	141.1
C6—C1—S1	118.96 (13)	H7D—C7—H7F	109.5
C3—C2—C1	118.95 (17)	H7E—C7—H7F	109.5
C3—C2—H2	120.5	O3—C8—N1	124.77 (17)
C1—C2—H2	120.5	O3—C8—C9	129.15 (19)
C2—C3—C4	121.40 (17)	N1—C8—C9	106.08 (17)
C2—C3—H3	119.3	C8—C9—C10	105.59 (17)
C4—C3—H3	119.3	C8—C9—H9A	110.6
C5—C4—C3	118.19 (17)	C10—C9—H9A	110.6
C5—C4—C7	120.87 (17)	C8—C9—H9B	110.6
C3—C4—C7	120.94 (17)	C10—C9—H9B	110.6
C6—C5—C4	121.66 (16)	H9A—C9—H9B	108.8
C6—C5—H5	119.2	C9—C10—C11	105.25 (17)
C4—C5—H5	119.2	C9—C10—H10A	110.7
C5—C6—C1	118.65 (16)	C11—C10—H10A	110.7
C5—C6—H6	120.7	C9—C10—H10B	110.7
C1—C6—H6	120.7	C11—C10—H10B	110.7
C4—C7—H7A	109.5	H10A—C10—H10B	108.8
C4—C7—H7B	109.5	N1—C11—C10	102.66 (17)
H7A—C7—H7B	109.5	N1—C11—H11A	111.2
C4—C7—H7C	109.5	C10—C11—H11A	111.2
H7A—C7—H7C	109.5	N1—C11—H11B	111.2
H7B—C7—H7C	109.5	C10—C11—H11B	111.2
C4—C7—H7D	109.5	H11A—C11—H11B	109.1
H7A—C7—H7D	141.1
O2—S1—N1—C8	−44.33 (17)	C2—C3—C4—C7	179.26 (17)
O1—S1—N1—C8	−172.80 (14)	C3—C4—C5—C6	−0.3 (3)
C1—S1—N1—C8	72.39 (15)	C7—C4—C5—C6	−179.70 (16)
O2—S1—N1—C11	136.12 (14)	C4—C5—C6—C1	0.7 (3)
O1—S1—N1—C11	7.65 (16)	C2—C1—C6—C5	−0.8 (2)
C1—S1—N1—C11	−107.16 (14)	S1—C1—C6—C5	179.61 (13)
O2—S1—C1—C2	8.15 (16)	C11—N1—C8—O3	176.42 (18)
O1—S1—C1—C2	140.60 (14)	S1—N1—C8—O3	−3.2 (3)
N1—S1—C1—C2	−108.03 (15)	C11—N1—C8—C9	−3.4 (2)
O2—S1—C1—C6	−172.22 (12)	S1—N1—C8—C9	177.03 (13)
O1—S1—C1—C6	−39.78 (15)	O3—C8—C9—C10	−161.7 (2)
N1—S1—C1—C6	71.60 (15)	N1—C8—C9—C10	18.1 (2)
C6—C1—C2—C3	0.3 (3)	C8—C9—C10—C11	−25.6 (2)
S1—C1—C2—C3	179.97 (14)	C8—N1—C11—C10	−12.5 (2)
C1—C2—C3—C4	0.1 (3)	S1—N1—C11—C10	167.08 (13)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—N1	22.9 (2)