5-Methyl-1-(p-tolyl­sulfon­yl)-2,3,4,5-tetra­hydro­cyclo­pentene[b]pyrrole

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.

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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Computing details

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

Crystal data

C15H19NO2S	F(000) = 592
Mr = 277.37	Dx = 1.326 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 723 reflections
a = 10.724 (2) Å	θ = 2.1–25.5°
b = 7.7050 (15) Å	µ = 0.23 mm^−1
c = 16.914 (3) Å	T = 291 K
β = 96.15 (3)°	Prism, colourless
V = 1389.5 (5) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	2712 independent reflections
Radiation source: sealed tube	2132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→12
Tmin = 0.95, Tmax = 0.96	k = −9→9
5264 measured reflections	l = −20→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 1.55P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2712 reflections	Δρmax = 0.69 e Å^−3
174 parameters	Δρmin = −0.52 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (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
C1	0.4690 (3)	0.2694 (5)	0.4508 (2)	0.0620 (9)
H1B	0.4935	0.3147	0.4019	0.093*
H1C	0.4248	0.3572	0.4769	0.093*
H1D	0.4153	0.1707	0.4397	0.093*
C2	0.5846 (3)	0.2150 (4)	0.50431 (18)	0.0443 (7)
C3	0.6906 (3)	0.1536 (4)	0.47324 (18)	0.0471 (7)
H3A	0.6898	0.1439	0.4184	0.057*
C4	0.7968 (3)	0.1065 (4)	0.52112 (17)	0.0422 (7)
H4A	0.8669	0.0665	0.4988	0.051*
C5	0.7987 (2)	0.1192 (3)	0.60308 (17)	0.0368 (6)
C6	0.6929 (3)	0.1773 (4)	0.63599 (18)	0.0433 (7)
H6A	0.6932	0.1844	0.6909	0.052*
C7	0.5876 (3)	0.2245 (4)	0.58670 (19)	0.0484 (7)
H7A	0.5170	0.2635	0.6089	0.058*
C8	1.0790 (2)	0.3338 (4)	0.61288 (16)	0.0378 (6)
H8A	1.0367	0.3050	0.5603	0.045*
C9	1.2172 (3)	0.2807 (4)	0.62164 (19)	0.0509 (8)
H9A	1.2296	0.1706	0.6492	0.061*
H9B	1.2490	0.2720	0.5702	0.061*
C10	1.2792 (3)	0.4257 (5)	0.6698 (2)	0.0550 (8)
H10	1.3610	0.4212	0.6944	0.066*
C11	1.2049 (3)	0.5597 (4)	0.67333 (19)	0.0528 (8)
H11	1.2288	0.6618	0.7001	0.063*
C12	1.0773 (3)	0.5314 (4)	0.62971 (17)	0.0424 (7)
H12A	1.0681	0.5971	0.5798	0.051*
C13	0.9654 (3)	0.5630 (4)	0.67649 (18)	0.0435 (7)
H13A	0.9813	0.6651	0.7106	0.052*
C14	0.8448 (3)	0.5877 (4)	0.6224 (2)	0.0558 (8)
H14A	0.8501	0.6921	0.5920	0.084*
H14B	0.7758	0.5962	0.6539	0.084*
H14C	0.8322	0.4904	0.5870	0.084*
C15	0.9649 (3)	0.4002 (4)	0.72759 (16)	0.0424 (7)
H15A	1.0191	0.4144	0.7768	0.051*
H15B	0.8807	0.3739	0.7401	0.051*
N	1.0123 (2)	0.2611 (3)	0.67821 (13)	0.0357 (5)
O1	0.90427 (19)	0.0247 (3)	0.74083 (12)	0.0513 (6)
O2	1.01533 (19)	−0.0314 (2)	0.62214 (13)	0.0499 (6)
S	0.93833 (6)	0.07856 (8)	0.66505 (4)	0.0380 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.057 (2)	0.056 (2)	0.070 (2)	0.0031 (16)	−0.0048 (17)	0.0032 (17)
C2	0.0437 (16)	0.0343 (14)	0.0544 (17)	−0.0042 (12)	0.0033 (13)	0.0018 (13)
C3	0.0543 (18)	0.0446 (16)	0.0429 (15)	−0.0049 (14)	0.0067 (13)	−0.0018 (13)
C4	0.0442 (15)	0.0373 (15)	0.0471 (16)	−0.0025 (12)	0.0147 (12)	−0.0074 (12)
C5	0.0381 (14)	0.0257 (12)	0.0477 (15)	−0.0036 (10)	0.0107 (11)	0.0001 (11)
C6	0.0431 (15)	0.0451 (16)	0.0438 (15)	−0.0026 (13)	0.0137 (12)	0.0007 (13)
C7	0.0390 (15)	0.0482 (17)	0.0596 (19)	0.0021 (13)	0.0133 (14)	−0.0027 (14)
C8	0.0395 (14)	0.0385 (14)	0.0362 (14)	−0.0046 (11)	0.0081 (11)	0.0000 (11)
C9	0.0437 (16)	0.0533 (18)	0.0582 (18)	−0.0013 (14)	0.0166 (14)	−0.0042 (15)
C10	0.0397 (16)	0.067 (2)	0.0585 (19)	−0.0094 (15)	0.0049 (14)	−0.0034 (17)
C11	0.0564 (19)	0.0456 (17)	0.0567 (18)	−0.0188 (15)	0.0078 (15)	−0.0050 (14)
C12	0.0513 (17)	0.0336 (14)	0.0424 (15)	−0.0048 (12)	0.0058 (13)	0.0069 (12)
C13	0.0533 (17)	0.0268 (13)	0.0511 (17)	0.0009 (12)	0.0082 (13)	−0.0017 (12)
C14	0.0534 (18)	0.0424 (17)	0.071 (2)	0.0050 (14)	0.0040 (16)	0.0074 (16)
C15	0.0535 (17)	0.0357 (14)	0.0397 (14)	−0.0003 (12)	0.0133 (12)	−0.0039 (12)
N	0.0402 (12)	0.0286 (11)	0.0397 (12)	−0.0012 (9)	0.0103 (10)	−0.0003 (9)
O1	0.0559 (12)	0.0450 (12)	0.0546 (12)	−0.0009 (10)	0.0128 (10)	0.0184 (10)
O2	0.0490 (12)	0.0298 (10)	0.0731 (14)	0.0064 (9)	0.0167 (10)	−0.0047 (9)
S	0.0398 (4)	0.0268 (3)	0.0486 (4)	0.0013 (3)	0.0099 (3)	0.0050 (3)

Geometric parameters (Å, º)

C1—C2	1.514 (4)	C9—H9A	0.9700
C1—H1B	0.9600	C9—H9B	0.9700
C1—H1C	0.9600	C10—C11	1.310 (5)
C1—H1D	0.9600	C10—H10	0.9300
C2—C3	1.386 (4)	C11—C12	1.499 (4)
C2—C7	1.393 (4)	C11—H11	0.9300
C3—C4	1.373 (4)	C12—C13	1.526 (4)
C3—H3A	0.9300	C12—H12A	0.9800
C4—C5	1.388 (4)	C13—C14	1.514 (4)
C4—H4A	0.9300	C13—C15	1.524 (4)
C5—C6	1.390 (4)	C13—H13A	0.9800
C5—S	1.761 (3)	C14—H14A	0.9600
C6—C7	1.379 (4)	C14—H14B	0.9600
C6—H6A	0.9300	C14—H14C	0.9600
C7—H7A	0.9300	C15—N	1.482 (3)
C8—N	1.489 (3)	C15—H15A	0.9700
C8—C9	1.530 (4)	C15—H15B	0.9700
C8—C12	1.549 (4)	N—S	1.618 (2)
C8—H8A	0.9800	O1—S	1.431 (2)
C9—C10	1.496 (4)	O2—S	1.433 (2)
C2—C1—H1B	109.5	C9—C10—H10	123.9
C2—C1—H1C	109.5	C10—C11—C12	113.0 (3)
H1B—C1—H1C	109.5	C10—C11—H11	123.5
C2—C1—H1D	109.5	C12—C11—H11	123.5
H1B—C1—H1D	109.5	C11—C12—C13	116.6 (2)
H1C—C1—H1D	109.5	C11—C12—C8	101.9 (2)
C3—C2—C7	117.8 (3)	C13—C12—C8	106.1 (2)
C3—C2—C1	121.4 (3)	C11—C12—H12A	110.6
C7—C2—C1	120.8 (3)	C13—C12—H12A	110.6
C4—C3—C2	121.9 (3)	C8—C12—H12A	110.6
C4—C3—H3A	119.0	C14—C13—C15	113.0 (3)
C2—C3—H3A	119.0	C14—C13—C12	112.0 (3)
C3—C4—C5	119.6 (3)	C15—C13—C12	102.3 (2)
C3—C4—H4A	120.2	C14—C13—H13A	109.7
C5—C4—H4A	120.2	C15—C13—H13A	109.7
C4—C5—C6	119.8 (3)	C12—C13—H13A	109.7
C4—C5—S	120.2 (2)	C13—C14—H14A	109.5
C6—C5—S	119.8 (2)	C13—C14—H14B	109.5
C7—C6—C5	119.6 (3)	H14A—C14—H14B	109.5
C7—C6—H6A	120.2	C13—C14—H14C	109.5
C5—C6—H6A	120.2	H14A—C14—H14C	109.5
C6—C7—C2	121.4 (3)	H14B—C14—H14C	109.5
C6—C7—H7A	119.3	N—C15—C13	104.7 (2)
C2—C7—H7A	119.3	N—C15—H15A	110.8
N—C8—C9	111.4 (2)	C13—C15—H15A	110.8
N—C8—C12	102.6 (2)	N—C15—H15B	110.8
C9—C8—C12	106.0 (2)	C13—C15—H15B	110.8
N—C8—H8A	112.1	H15A—C15—H15B	108.9
C9—C8—H8A	112.1	C15—N—C8	111.6 (2)
C12—C8—H8A	112.1	C15—N—S	120.90 (18)
C10—C9—C8	102.8 (3)	C8—N—S	119.50 (17)
C10—C9—H9A	111.2	O1—S—O2	119.88 (13)
C8—C9—H9A	111.2	O1—S—N	107.29 (13)
C10—C9—H9B	111.2	O2—S—N	106.43 (12)
C8—C9—H9B	111.2	O1—S—C5	107.59 (13)
H9A—C9—H9B	109.1	O2—S—C5	107.63 (13)
C11—C10—C9	112.1 (3)	N—S—C5	107.47 (12)
C11—C10—H10	123.9
C7—C2—C3—C4	−1.4 (4)	C11—C12—C13—C15	−77.0 (3)
C1—C2—C3—C4	178.9 (3)	C8—C12—C13—C15	35.6 (3)
C2—C3—C4—C5	0.5 (4)	C14—C13—C15—N	88.3 (3)
C3—C4—C5—C6	0.7 (4)	C12—C13—C15—N	−32.4 (3)
C3—C4—C5—S	−174.2 (2)	C13—C15—N—C8	18.1 (3)
C4—C5—C6—C7	−1.0 (4)	C13—C15—N—S	−130.5 (2)
S—C5—C6—C7	173.9 (2)	C9—C8—N—C15	116.9 (3)
C5—C6—C7—C2	0.1 (4)	C12—C8—N—C15	4.0 (3)
C3—C2—C7—C6	1.1 (4)	C9—C8—N—S	−94.0 (2)
C1—C2—C7—C6	−179.2 (3)	C12—C8—N—S	153.03 (18)
N—C8—C9—C10	−91.0 (3)	C15—N—S—O1	−44.6 (2)
C12—C8—C9—C10	19.8 (3)	C8—N—S—O1	169.27 (19)
C8—C9—C10—C11	−13.5 (4)	C15—N—S—O2	−174.1 (2)
C9—C10—C11—C12	1.1 (4)	C8—N—S—O2	39.8 (2)
C10—C11—C12—C13	126.6 (3)	C15—N—S—C5	70.9 (2)
C10—C11—C12—C8	11.6 (3)	C8—N—S—C5	−75.3 (2)
N—C8—C12—C11	97.9 (2)	C4—C5—S—O1	−154.6 (2)
C9—C8—C12—C11	−19.1 (3)	C6—C5—S—O1	30.5 (3)
N—C8—C12—C13	−24.7 (3)	C4—C5—S—O2	−24.1 (3)
C9—C8—C12—C13	−141.6 (2)	C6—C5—S—O2	161.0 (2)
C11—C12—C13—C14	161.6 (3)	C4—C5—S—N	90.1 (2)
C8—C12—C13—C14	−85.8 (3)	C6—C5—S—N	−84.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2^i	0.93	2.53	3.363 (3)	149

Symmetry code: (i) −x+2, −y, −z+1.