Crystal structure of 1-[(4-methylbenzene)sulfonyl]pyrrolidine

The crystal structure of a pyrrolidine-substituted p-toluene­sulfonamide is described. The crystal structure features both intra- and inter­molecular C—H...O hydrogen bonds, as well as inter­molecular C—H...π and π–π inter­actions, leading to the formation of sheets parallel to the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.120
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.974 Why?
PLAT241_ALERT_2_C High   MainMol Ueq as Compared to Neighbors of         C3 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         52 Report
PLAT977_ALERT_2_C Check Negative Difference Density on H11C             -0.31 eA-3

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

1-[(4-Methylbenzene)sulfonyl]pyrrolidine

Crystal data

C11H15NO2S	Z = 2
Mr = 225.30	F(000) = 240
Triclinic, P1	Dx = 1.364 Mg m^−3
a = 7.5347 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.2581 (1) Å	Cell parameters from 3988 reflections
c = 9.6157 (1) Å	θ = 4.7–68.2°
α = 77.876 (1)°	µ = 2.46 mm^−1
β = 86.132 (1)°	T = 173 K
γ = 69.682 (1)°	Plate, colourless
V = 548.56 (1) Å^3	0.22 × 0.16 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	1715 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.033
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 68.3°, θmin = 4.7°
Tmin = 0.631, Tmax = 0.753	h = −9→9
7120 measured reflections	k = −9→9
1944 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.2666P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1944 reflections	Δρmax = 0.53 e Å^−3
137 parameters	Δρmin = −0.33 e Å^−3
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
S1	0.56522 (7)	0.19952 (7)	0.20258 (5)	0.0225 (2)
O1	0.6545 (2)	0.2957 (2)	0.09657 (16)	0.0302 (4)
O2	0.6789 (2)	0.0403 (2)	0.29321 (17)	0.0313 (4)
N1	0.4193 (3)	0.1465 (2)	0.11936 (19)	0.0239 (4)
C1	0.3110 (3)	0.0415 (3)	0.2046 (2)	0.0283 (5)
H1A	0.263738	0.084458	0.293341	0.034*
H1B	0.389620	−0.084784	0.228939	0.034*
C2	0.1485 (3)	0.0702 (3)	0.1065 (3)	0.0353 (6)
H2A	0.184331	−0.016766	0.043620	0.042*
H2B	0.035011	0.061924	0.161429	0.042*
C3	0.1137 (4)	0.2554 (4)	0.0214 (4)	0.0511 (8)
H3A	0.051601	0.272209	−0.070616	0.061*
H3B	0.032278	0.344031	0.074899	0.061*
C4	0.3053 (4)	0.2719 (3)	−0.0018 (3)	0.0357 (6)
H4A	0.359019	0.240275	−0.093216	0.043*
H4B	0.299424	0.393584	−0.001822	0.043*
C5	0.4298 (3)	0.3438 (3)	0.3132 (2)	0.0225 (5)
C6	0.3318 (3)	0.5190 (3)	0.2538 (2)	0.0287 (5)
H6	0.342164	0.563001	0.155156	0.034*
C7	0.2192 (3)	0.6284 (3)	0.3400 (3)	0.0331 (6)
H7	0.149316	0.747265	0.299159	0.040*
C8	0.2063 (3)	0.5674 (4)	0.4859 (3)	0.0334 (6)
C9	0.3052 (4)	0.3933 (4)	0.5423 (3)	0.0359 (6)
H9	0.296907	0.349698	0.641258	0.043*
C10	0.4167 (3)	0.2805 (3)	0.4575 (2)	0.0296 (5)
H10	0.483503	0.160696	0.497955	0.035*
C11	0.0852 (4)	0.6900 (4)	0.5788 (3)	0.0516 (8)
H11A	0.096515	0.806829	0.547317	0.077*
H11B	0.127699	0.643344	0.677852	0.077*
H11C	−0.047268	0.699432	0.571301	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0196 (3)	0.0255 (3)	0.0225 (3)	−0.0078 (2)	−0.00028 (19)	−0.0042 (2)
O1	0.0262 (8)	0.0370 (10)	0.0289 (9)	−0.0143 (7)	0.0064 (6)	−0.0056 (7)
O2	0.0243 (8)	0.0313 (9)	0.0345 (9)	−0.0062 (7)	−0.0048 (7)	−0.0023 (7)
N1	0.0240 (9)	0.0269 (10)	0.0223 (9)	−0.0101 (8)	−0.0003 (7)	−0.0057 (7)
C1	0.0278 (11)	0.0262 (12)	0.0327 (12)	−0.0117 (9)	−0.0001 (9)	−0.0051 (9)
C2	0.0280 (12)	0.0392 (15)	0.0423 (15)	−0.0142 (10)	−0.0049 (10)	−0.0095 (11)
C3	0.0361 (15)	0.0509 (18)	0.0596 (19)	−0.0150 (13)	−0.0176 (13)	0.0090 (14)
C4	0.0395 (14)	0.0379 (14)	0.0281 (13)	−0.0140 (11)	−0.0081 (10)	0.0005 (10)
C5	0.0217 (10)	0.0269 (12)	0.0224 (11)	−0.0113 (9)	−0.0004 (8)	−0.0069 (8)
C6	0.0318 (12)	0.0295 (13)	0.0267 (12)	−0.0141 (10)	0.0011 (9)	−0.0039 (9)
C7	0.0316 (12)	0.0262 (13)	0.0443 (15)	−0.0114 (10)	0.0041 (10)	−0.0118 (10)
C8	0.0288 (12)	0.0453 (15)	0.0383 (14)	−0.0212 (11)	0.0072 (10)	−0.0215 (11)
C9	0.0370 (13)	0.0553 (17)	0.0224 (12)	−0.0224 (12)	0.0024 (10)	−0.0119 (11)
C10	0.0302 (12)	0.0361 (14)	0.0225 (11)	−0.0122 (10)	−0.0032 (9)	−0.0035 (9)
C11	0.0418 (15)	0.070 (2)	0.0624 (19)	−0.0267 (15)	0.0161 (14)	−0.0471 (17)

Geometric parameters (Å, º)

S1—O1	1.4357 (16)	C4—H4B	0.9900
S1—O2	1.4349 (16)	C5—C6	1.390 (3)
S1—N1	1.6248 (18)	C5—C10	1.386 (3)
S1—C5	1.770 (2)	C6—H6	0.9500
N1—C1	1.481 (3)	C6—C7	1.382 (3)
N1—C4	1.476 (3)	C7—H7	0.9500
C1—H1A	0.9900	C7—C8	1.397 (4)
C1—H1B	0.9900	C8—C9	1.379 (4)
C1—C2	1.518 (3)	C8—C11	1.511 (3)
C2—H2A	0.9900	C9—H9	0.9500
C2—H2B	0.9900	C9—C10	1.386 (3)
C2—C3	1.517 (4)	C10—H10	0.9500
C3—H3A	0.9900	C11—H11A	0.9800
C3—H3B	0.9900	C11—H11B	0.9800
C3—C4	1.495 (4)	C11—H11C	0.9800
C4—H4A	0.9900
O1—S1—N1	106.88 (9)	N1—C4—H4B	110.9
O1—S1—C5	108.04 (10)	C3—C4—H4A	110.9
O2—S1—O1	119.67 (10)	C3—C4—H4B	110.9
O2—S1—N1	106.48 (10)	H4A—C4—H4B	108.9
O2—S1—C5	107.59 (10)	C6—C5—S1	119.68 (17)
N1—S1—C5	107.66 (9)	C10—C5—S1	120.00 (18)
C1—N1—S1	118.02 (14)	C10—C5—C6	120.3 (2)
C4—N1—S1	120.69 (16)	C5—C6—H6	120.4
C4—N1—C1	110.89 (17)	C7—C6—C5	119.2 (2)
N1—C1—H1A	111.1	C7—C6—H6	120.4
N1—C1—H1B	111.1	C6—C7—H7	119.4
N1—C1—C2	103.35 (18)	C6—C7—C8	121.3 (2)
H1A—C1—H1B	109.1	C8—C7—H7	119.4
C2—C1—H1A	111.1	C7—C8—C11	120.4 (3)
C2—C1—H1B	111.1	C9—C8—C7	118.4 (2)
C1—C2—H2A	111.1	C9—C8—C11	121.2 (3)
C1—C2—H2B	111.1	C8—C9—H9	119.3
H2A—C2—H2B	109.1	C8—C9—C10	121.3 (2)
C3—C2—C1	103.2 (2)	C10—C9—H9	119.3
C3—C2—H2A	111.1	C5—C10—C9	119.5 (2)
C3—C2—H2B	111.1	C5—C10—H10	120.2
C2—C3—H3A	110.7	C9—C10—H10	120.2
C2—C3—H3B	110.7	C8—C11—H11A	109.5
H3A—C3—H3B	108.8	C8—C11—H11B	109.5
C4—C3—C2	105.2 (2)	C8—C11—H11C	109.5
C4—C3—H3A	110.7	H11A—C11—H11B	109.5
C4—C3—H3B	110.7	H11A—C11—H11C	109.5
N1—C4—C3	104.3 (2)	H11B—C11—H11C	109.5
N1—C4—H4A	110.9
S1—N1—C1—C2	161.32 (16)	C1—N1—C4—C3	6.5 (3)
S1—N1—C4—C3	−137.8 (2)	C1—C2—C3—C4	36.6 (3)
S1—C5—C6—C7	176.88 (17)	C2—C3—C4—N1	−26.6 (3)
S1—C5—C10—C9	−177.89 (17)	C4—N1—C1—C2	16.0 (2)
O1—S1—N1—C1	178.52 (15)	C5—S1—N1—C1	−65.62 (18)
O1—S1—N1—C4	−39.71 (19)	C5—S1—N1—C4	76.16 (19)
O1—S1—C5—C6	38.27 (19)	C5—C6—C7—C8	1.8 (3)
O1—S1—C5—C10	−143.93 (18)	C6—C5—C10—C9	−0.1 (3)
O2—S1—N1—C1	49.53 (18)	C6—C7—C8—C9	−1.6 (3)
O2—S1—N1—C4	−168.70 (17)	C6—C7—C8—C11	178.9 (2)
O2—S1—C5—C6	168.76 (16)	C7—C8—C9—C10	0.5 (3)
O2—S1—C5—C10	−13.4 (2)	C8—C9—C10—C5	0.3 (3)
N1—S1—C5—C6	−76.84 (19)	C10—C5—C6—C7	−0.9 (3)
N1—S1—C5—C10	100.97 (19)	C11—C8—C9—C10	−179.9 (2)
N1—C1—C2—C3	−31.6 (3)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	0.95	2.46	3.406 (3)	174
C10—H10···O2	0.95	2.54	2.917 (3)	104
C11—H11C···Cg2^ii	0.98	2.73	3.614 (3)	150

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