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The title compound, C15H19NO2S, is a bicyclic pyrrole derivative synthesized by an intra­molecular C—C coupling reaction. The mol­ecules are connected via weak C—H...O inter­actions, forming dimers in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041444/ob2074sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041444/ob2074Isup2.hkl
Contains datablock I

CCDC reference: 628024

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C)= 0.005 Å
  • R factor = 0.046
  • wR factor = 0.143
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

5-Methyl-1-(p-tolylsulfonyl)-2,3,4,5- tetrahydrocyclopentene[b]pyrrole top
Crystal data top
C15H19NO2SF(000) = 592
Mr = 277.37Dx = 1.326 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 723 reflections
a = 10.724 (2) Åθ = 2.1–25.5°
b = 7.7050 (15) ŵ = 0.23 mm1
c = 16.914 (3) ÅT = 291 K
β = 96.15 (3)°Prism, colourless
V = 1389.5 (5) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2712 independent reflections
Radiation source: sealed tube2132 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 812
Tmin = 0.95, Tmax = 0.96k = 99
5264 measured reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.06P)2 + 1.55P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2712 reflectionsΔρmax = 0.69 e Å3
174 parametersΔρmin = 0.52 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.027 (3)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.4690 (3)0.2694 (5)0.4508 (2)0.0620 (9)
H1B0.49350.31470.40190.093*
H1C0.42480.35720.47690.093*
H1D0.41530.17070.43970.093*
C20.5846 (3)0.2150 (4)0.50431 (18)0.0443 (7)
C30.6906 (3)0.1536 (4)0.47324 (18)0.0471 (7)
H3A0.68980.14390.41840.057*
C40.7968 (3)0.1065 (4)0.52112 (17)0.0422 (7)
H4A0.86690.06650.49880.051*
C50.7987 (2)0.1192 (3)0.60308 (17)0.0368 (6)
C60.6929 (3)0.1773 (4)0.63599 (18)0.0433 (7)
H6A0.69320.18440.69090.052*
C70.5876 (3)0.2245 (4)0.58670 (19)0.0484 (7)
H7A0.51700.26350.60890.058*
C81.0790 (2)0.3338 (4)0.61288 (16)0.0378 (6)
H8A1.03670.30500.56030.045*
C91.2172 (3)0.2807 (4)0.62164 (19)0.0509 (8)
H9A1.22960.17060.64920.061*
H9B1.24900.27200.57020.061*
C101.2792 (3)0.4257 (5)0.6698 (2)0.0550 (8)
H101.36100.42120.69440.066*
C111.2049 (3)0.5597 (4)0.67333 (19)0.0528 (8)
H111.22880.66180.70010.063*
C121.0773 (3)0.5314 (4)0.62971 (17)0.0424 (7)
H12A1.06810.59710.57980.051*
C130.9654 (3)0.5630 (4)0.67649 (18)0.0435 (7)
H13A0.98130.66510.71060.052*
C140.8448 (3)0.5877 (4)0.6224 (2)0.0558 (8)
H14A0.85010.69210.59200.084*
H14B0.77580.59620.65390.084*
H14C0.83220.49040.58700.084*
C150.9649 (3)0.4002 (4)0.72759 (16)0.0424 (7)
H15A1.01910.41440.77680.051*
H15B0.88070.37390.74010.051*
N1.0123 (2)0.2611 (3)0.67821 (13)0.0357 (5)
O10.90427 (19)0.0247 (3)0.74083 (12)0.0513 (6)
O21.01533 (19)0.0314 (2)0.62214 (13)0.0499 (6)
S0.93833 (6)0.07856 (8)0.66505 (4)0.0380 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.057 (2)0.056 (2)0.070 (2)0.0031 (16)0.0048 (17)0.0032 (17)
C20.0437 (16)0.0343 (14)0.0544 (17)0.0042 (12)0.0033 (13)0.0018 (13)
C30.0543 (18)0.0446 (16)0.0429 (15)0.0049 (14)0.0067 (13)0.0018 (13)
C40.0442 (15)0.0373 (15)0.0471 (16)0.0025 (12)0.0147 (12)0.0074 (12)
C50.0381 (14)0.0257 (12)0.0477 (15)0.0036 (10)0.0107 (11)0.0001 (11)
C60.0431 (15)0.0451 (16)0.0438 (15)0.0026 (13)0.0137 (12)0.0007 (13)
C70.0390 (15)0.0482 (17)0.0596 (19)0.0021 (13)0.0133 (14)0.0027 (14)
C80.0395 (14)0.0385 (14)0.0362 (14)0.0046 (11)0.0081 (11)0.0000 (11)
C90.0437 (16)0.0533 (18)0.0582 (18)0.0013 (14)0.0166 (14)0.0042 (15)
C100.0397 (16)0.067 (2)0.0585 (19)0.0094 (15)0.0049 (14)0.0034 (17)
C110.0564 (19)0.0456 (17)0.0567 (18)0.0188 (15)0.0078 (15)0.0050 (14)
C120.0513 (17)0.0336 (14)0.0424 (15)0.0048 (12)0.0058 (13)0.0069 (12)
C130.0533 (17)0.0268 (13)0.0511 (17)0.0009 (12)0.0082 (13)0.0017 (12)
C140.0534 (18)0.0424 (17)0.071 (2)0.0050 (14)0.0040 (16)0.0074 (16)
C150.0535 (17)0.0357 (14)0.0397 (14)0.0003 (12)0.0133 (12)0.0039 (12)
N0.0402 (12)0.0286 (11)0.0397 (12)0.0012 (9)0.0103 (10)0.0003 (9)
O10.0559 (12)0.0450 (12)0.0546 (12)0.0009 (10)0.0128 (10)0.0184 (10)
O20.0490 (12)0.0298 (10)0.0731 (14)0.0064 (9)0.0167 (10)0.0047 (9)
S0.0398 (4)0.0268 (3)0.0486 (4)0.0013 (3)0.0099 (3)0.0050 (3)
Geometric parameters (Å, º) top
C1—C21.514 (4)C9—H9A0.9700
C1—H1B0.9600C9—H9B0.9700
C1—H1C0.9600C10—C111.310 (5)
C1—H1D0.9600C10—H100.9300
C2—C31.386 (4)C11—C121.499 (4)
C2—C71.393 (4)C11—H110.9300
C3—C41.373 (4)C12—C131.526 (4)
C3—H3A0.9300C12—H12A0.9800
C4—C51.388 (4)C13—C141.514 (4)
C4—H4A0.9300C13—C151.524 (4)
C5—C61.390 (4)C13—H13A0.9800
C5—S1.761 (3)C14—H14A0.9600
C6—C71.379 (4)C14—H14B0.9600
C6—H6A0.9300C14—H14C0.9600
C7—H7A0.9300C15—N1.482 (3)
C8—N1.489 (3)C15—H15A0.9700
C8—C91.530 (4)C15—H15B0.9700
C8—C121.549 (4)N—S1.618 (2)
C8—H8A0.9800O1—S1.431 (2)
C9—C101.496 (4)O2—S1.433 (2)
C2—C1—H1B109.5C9—C10—H10123.9
C2—C1—H1C109.5C10—C11—C12113.0 (3)
H1B—C1—H1C109.5C10—C11—H11123.5
C2—C1—H1D109.5C12—C11—H11123.5
H1B—C1—H1D109.5C11—C12—C13116.6 (2)
H1C—C1—H1D109.5C11—C12—C8101.9 (2)
C3—C2—C7117.8 (3)C13—C12—C8106.1 (2)
C3—C2—C1121.4 (3)C11—C12—H12A110.6
C7—C2—C1120.8 (3)C13—C12—H12A110.6
C4—C3—C2121.9 (3)C8—C12—H12A110.6
C4—C3—H3A119.0C14—C13—C15113.0 (3)
C2—C3—H3A119.0C14—C13—C12112.0 (3)
C3—C4—C5119.6 (3)C15—C13—C12102.3 (2)
C3—C4—H4A120.2C14—C13—H13A109.7
C5—C4—H4A120.2C15—C13—H13A109.7
C4—C5—C6119.8 (3)C12—C13—H13A109.7
C4—C5—S120.2 (2)C13—C14—H14A109.5
C6—C5—S119.8 (2)C13—C14—H14B109.5
C7—C6—C5119.6 (3)H14A—C14—H14B109.5
C7—C6—H6A120.2C13—C14—H14C109.5
C5—C6—H6A120.2H14A—C14—H14C109.5
C6—C7—C2121.4 (3)H14B—C14—H14C109.5
C6—C7—H7A119.3N—C15—C13104.7 (2)
C2—C7—H7A119.3N—C15—H15A110.8
N—C8—C9111.4 (2)C13—C15—H15A110.8
N—C8—C12102.6 (2)N—C15—H15B110.8
C9—C8—C12106.0 (2)C13—C15—H15B110.8
N—C8—H8A112.1H15A—C15—H15B108.9
C9—C8—H8A112.1C15—N—C8111.6 (2)
C12—C8—H8A112.1C15—N—S120.90 (18)
C10—C9—C8102.8 (3)C8—N—S119.50 (17)
C10—C9—H9A111.2O1—S—O2119.88 (13)
C8—C9—H9A111.2O1—S—N107.29 (13)
C10—C9—H9B111.2O2—S—N106.43 (12)
C8—C9—H9B111.2O1—S—C5107.59 (13)
H9A—C9—H9B109.1O2—S—C5107.63 (13)
C11—C10—C9112.1 (3)N—S—C5107.47 (12)
C11—C10—H10123.9
C7—C2—C3—C41.4 (4)C11—C12—C13—C1577.0 (3)
C1—C2—C3—C4178.9 (3)C8—C12—C13—C1535.6 (3)
C2—C3—C4—C50.5 (4)C14—C13—C15—N88.3 (3)
C3—C4—C5—C60.7 (4)C12—C13—C15—N32.4 (3)
C3—C4—C5—S174.2 (2)C13—C15—N—C818.1 (3)
C4—C5—C6—C71.0 (4)C13—C15—N—S130.5 (2)
S—C5—C6—C7173.9 (2)C9—C8—N—C15116.9 (3)
C5—C6—C7—C20.1 (4)C12—C8—N—C154.0 (3)
C3—C2—C7—C61.1 (4)C9—C8—N—S94.0 (2)
C1—C2—C7—C6179.2 (3)C12—C8—N—S153.03 (18)
N—C8—C9—C1091.0 (3)C15—N—S—O144.6 (2)
C12—C8—C9—C1019.8 (3)C8—N—S—O1169.27 (19)
C8—C9—C10—C1113.5 (4)C15—N—S—O2174.1 (2)
C9—C10—C11—C121.1 (4)C8—N—S—O239.8 (2)
C10—C11—C12—C13126.6 (3)C15—N—S—C570.9 (2)
C10—C11—C12—C811.6 (3)C8—N—S—C575.3 (2)
N—C8—C12—C1197.9 (2)C4—C5—S—O1154.6 (2)
C9—C8—C12—C1119.1 (3)C6—C5—S—O130.5 (3)
N—C8—C12—C1324.7 (3)C4—C5—S—O224.1 (3)
C9—C8—C12—C13141.6 (2)C6—C5—S—O2161.0 (2)
C11—C12—C13—C14161.6 (3)C4—C5—S—N90.1 (2)
C8—C12—C13—C1485.8 (3)C6—C5—S—N84.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O2i0.932.533.363 (3)149
Symmetry code: (i) x+2, y, z+1.
 

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