3-Ethyl-1-(4-methyl­phenyl­sulfonyl)-4-phenethyl-4,5-di­hydro­pyrrole

The title compound, C₂₁H₂₅NO₂S, crystallizes in a centrosymmetric triclinic unit cell. In the mol­ecule, the bond lengths and angles are normal, and the di­hydro­pyrrole five-membered ring is almost planar.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.160
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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

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

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Computing details

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

3-Ethyl-1-(4-methylphenylsulfonyl)-4-phenethyl-4,5-dihydropyrrole

Crystal data

C21H25NO2S	Z = 2
Mr = 355.48	F(000) = 380
Triclinic, P1	Dx = 1.248 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.250 (2) Å	Cell parameters from 25 reflections
b = 10.740 (2) Å	θ = 2.1–26.7°
c = 12.020 (2) Å	µ = 0.19 mm^−1
α = 66.05 (3)°	T = 293 K
β = 76.82 (3)°	Needle, colourless
γ = 81.95 (3)°	0.3 × 0.25 × 0.2 mm
V = 946.3 (4) Å^3

Data collection

Bruker P4 diffractometer	1852 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.041
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = 0→9
Absorption correction: ψ scan (SHELXTL; Bruker, 2000)	k = −12→12
Tmin = 0.95, Tmax = 0.96	l = −13→14
3583 measured reflections	3 standard reflections every 97 reflections
3330 independent reflections	intensity decay: 0.001%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0753P)^2 + 0.1421P] where P = (Fo^2 + 2Fc^2)/3
3330 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.19 e Å^−3
6 restraints	Δρmin = −0.31 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.3639 (0.0105) x + 8.1775 (0.0118) y + 1.1362 (0.0189) z = 2.2885 (0.0084)

* -0.0196 (0.0019) N * 0.0216 (0.0020) C5 * -0.0133 (0.0021) C4 * 0.0113 (0.0020) C6 * 0.0000 (0.0020) C7

Rms deviation of fitted atoms = 0.0152

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
S1	0.22026 (12)	0.15212 (10)	0.57309 (8)	0.0649 (3)
O1	0.0880 (3)	0.1860 (3)	0.6575 (2)	0.0912 (9)
O2	0.3332 (3)	0.0372 (2)	0.6176 (2)	0.0758 (7)
N	0.1331 (3)	0.1237 (3)	0.4785 (2)	0.0556 (7)
C1	0.5920 (5)	0.6519 (4)	0.2235 (4)	0.0956 (14)
H1B	0.6947	0.6248	0.1806	0.143*
H1C	0.6151	0.7060	0.2645	0.143*
H1D	0.5216	0.7047	0.1652	0.143*
C2	0.3523 (6)	−0.0275 (5)	0.1897 (4)	0.1006 (15)
H2B	0.3830	−0.0432	0.1143	0.151*
H2C	0.3034	−0.1070	0.2555	0.151*
H2D	0.4497	−0.0087	0.2101	0.151*
C3	0.2315 (6)	0.0892 (4)	0.1730 (4)	0.0871 (13)
H3A	0.1355	0.0698	0.1500	0.105*
H3B	0.2814	0.1679	0.1045	0.105*
C4	0.1723 (4)	0.1258 (3)	0.2831 (3)	0.0565 (9)
C5	0.2296 (4)	0.0781 (3)	0.3869 (3)	0.0557 (9)
H5A	0.3244	0.0200	0.3993	0.067*
C6	0.0018 (4)	0.2217 (3)	0.4193 (3)	0.0632 (10)
H6A	0.0143	0.3119	0.4154	0.076*
H6B	−0.1081	0.1924	0.4661	0.076*
C7	0.0249 (4)	0.2234 (3)	0.2889 (3)	0.0608 (9)
H7A	−0.0729	0.1854	0.2834	0.073*
C8	0.0468 (4)	0.3654 (3)	0.1850 (3)	0.0613 (10)
H8A	0.0442	0.3592	0.1072	0.074*
H8B	−0.0467	0.4256	0.2008	0.074*
C9	0.2082 (4)	0.4287 (3)	0.1716 (3)	0.0551 (9)
H9A	0.2238	0.4160	0.2532	0.066*
H9B	0.3010	0.3810	0.1369	0.066*
C10	0.2108 (4)	0.5776 (3)	0.0911 (3)	0.0477 (8)
C11	0.1152 (4)	0.6721 (4)	0.1314 (3)	0.0616 (9)
H11A	0.0497	0.6423	0.2105	0.074*
C12	0.1135 (5)	0.8101 (4)	0.0582 (4)	0.0712 (10)
H12A	0.0470	0.8720	0.0874	0.085*
C13	0.2118 (5)	0.8549 (4)	−0.0589 (4)	0.0696 (10)
H13A	0.2123	0.9475	−0.1091	0.084*
C14	0.3078 (4)	0.7632 (3)	−0.1005 (3)	0.0611 (9)
H14A	0.3738	0.7934	−0.1793	0.073*
C15	0.3083 (4)	0.6262 (3)	−0.0270 (3)	0.0533 (8)
H15A	0.3751	0.5650	−0.0569	0.064*
C21	0.3535 (5)	0.5391 (4)	0.3931 (4)	0.0709 (11)
H21A	0.3084	0.6253	0.3877	0.085*
C22	0.2686 (5)	0.4253 (4)	0.4756 (3)	0.0650 (10)
H22A	0.1667	0.4349	0.5247	0.078*
C23	0.3355 (4)	0.2972 (3)	0.4848 (3)	0.0521 (8)
C24	0.4884 (4)	0.2830 (3)	0.4126 (3)	0.0558 (9)
H24A	0.5351	0.1969	0.4191	0.067*
C25	0.5701 (4)	0.3983 (4)	0.3312 (3)	0.0635 (9)
H25A	0.6731	0.3884	0.2835	0.076*
C26	0.5053 (5)	0.5270 (4)	0.3180 (3)	0.0634 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0702 (6)	0.0663 (6)	0.0410 (5)	−0.0074 (5)	0.0026 (4)	−0.0092 (4)
O1	0.095 (2)	0.104 (2)	0.0568 (15)	−0.0167 (16)	0.0293 (15)	−0.0318 (15)
O2	0.0808 (14)	0.0693 (13)	0.0512 (12)	−0.0007 (11)	−0.0126 (11)	0.0020 (10)
N	0.0523 (16)	0.0514 (16)	0.0475 (16)	−0.0073 (13)	0.0034 (14)	−0.0088 (14)
C1	0.096 (3)	0.075 (3)	0.102 (3)	−0.028 (2)	−0.009 (3)	−0.018 (2)
C2	0.097 (3)	0.104 (4)	0.109 (4)	−0.006 (3)	−0.007 (3)	−0.056 (3)
C3	0.110 (3)	0.075 (3)	0.085 (3)	0.003 (3)	−0.029 (3)	−0.037 (2)
C4	0.062 (2)	0.0447 (19)	0.056 (2)	−0.0111 (17)	−0.0094 (18)	−0.0114 (17)
C5	0.055 (2)	0.0406 (18)	0.061 (2)	−0.0085 (15)	−0.0041 (18)	−0.0103 (17)
C6	0.0437 (19)	0.053 (2)	0.071 (2)	−0.0082 (16)	0.0020 (17)	−0.0073 (18)
C7	0.053 (2)	0.054 (2)	0.068 (2)	−0.0153 (17)	−0.0142 (18)	−0.0109 (18)
C8	0.050 (2)	0.055 (2)	0.067 (2)	−0.0098 (16)	−0.0161 (18)	−0.0072 (18)
C9	0.0414 (18)	0.0505 (19)	0.057 (2)	−0.0058 (15)	−0.0067 (15)	−0.0049 (16)
C10	0.0392 (17)	0.0516 (19)	0.0459 (18)	−0.0049 (15)	−0.0081 (15)	−0.0115 (16)
C11	0.057 (2)	0.066 (2)	0.048 (2)	−0.0051 (18)	0.0041 (17)	−0.0139 (18)
C12	0.074 (3)	0.062 (2)	0.072 (3)	0.0069 (19)	−0.004 (2)	−0.028 (2)
C13	0.082 (3)	0.047 (2)	0.067 (2)	−0.007 (2)	−0.016 (2)	−0.0080 (19)
C14	0.063 (2)	0.058 (2)	0.0458 (19)	−0.0118 (18)	0.0017 (17)	−0.0073 (18)
C15	0.0508 (19)	0.057 (2)	0.0463 (19)	−0.0037 (16)	−0.0038 (16)	−0.0168 (17)
C21	0.083 (3)	0.060 (2)	0.078 (3)	−0.001 (2)	−0.019 (2)	−0.034 (2)
C22	0.065 (2)	0.072 (3)	0.061 (2)	−0.003 (2)	−0.0008 (19)	−0.034 (2)
C23	0.054 (2)	0.058 (2)	0.0415 (17)	−0.0032 (16)	−0.0064 (16)	−0.0179 (16)
C24	0.051 (2)	0.057 (2)	0.054 (2)	0.0002 (17)	−0.0117 (17)	−0.0169 (17)
C25	0.050 (2)	0.072 (3)	0.064 (2)	−0.0038 (19)	−0.0080 (18)	−0.023 (2)
C26	0.066 (2)	0.064 (2)	0.060 (2)	−0.016 (2)	−0.011 (2)	−0.0205 (19)

Geometric parameters (Å, º)

S1—O1	1.427 (3)	C8—H8A	0.9700
S1—O2	1.431 (2)	C8—H8B	0.9700
S1—N	1.618 (3)	C9—C10	1.495 (4)
S1—C23	1.752 (3)	C9—H9A	0.9700
N—C5	1.419 (4)	C9—H9B	0.9700
N—C6	1.487 (4)	C10—C11	1.374 (4)
C1—C26	1.504 (5)	C10—C15	1.389 (4)
C1—H1B	0.9600	C11—C12	1.383 (4)
C1—H1C	0.9600	C11—H11A	0.9300
C1—H1D	0.9600	C12—C13	1.382 (5)
C2—C3	1.463 (5)	C12—H12A	0.9300
C2—H2B	0.9600	C13—C14	1.359 (5)
C2—H2C	0.9600	C13—H13A	0.9300
C2—H2D	0.9600	C14—C15	1.375 (4)
C3—C4	1.489 (5)	C14—H14A	0.9300
C3—H3A	0.9700	C15—H15A	0.9300
C3—H3B	0.9700	C21—C22	1.381 (5)
C4—C5	1.313 (4)	C21—C26	1.391 (5)
C4—C7	1.499 (5)	C21—H21A	0.9300
C5—H5A	0.9300	C22—C23	1.379 (4)
C6—C7	1.528 (5)	C22—H22A	0.9300
C6—H6A	0.9700	C23—C24	1.386 (4)
C6—H6B	0.9700	C24—C25	1.376 (5)
C7—C8	1.532 (4)	C24—H24A	0.9300
C7—H7A	0.9800	C25—C26	1.370 (5)
C8—C9	1.525 (4)	C25—H25A	0.9300
O1—S1—O2	120.40 (16)	C7—C8—H8A	108.8
O1—S1—N	106.26 (17)	C9—C8—H8B	108.8
O2—S1—N	106.13 (15)	C7—C8—H8B	108.8
O1—S1—C23	107.92 (17)	H8A—C8—H8B	107.6
O2—S1—C23	108.73 (16)	C10—C9—C8	113.4 (3)
N—S1—C23	106.61 (14)	C10—C9—H9A	108.9
C5—N—C6	106.2 (3)	C8—C9—H9A	108.9
C5—N—S1	120.9 (2)	C10—C9—H9B	108.9
C6—N—S1	120.1 (2)	C8—C9—H9B	108.9
C26—C1—H1B	109.5	H9A—C9—H9B	107.7
C26—C1—H1C	109.5	C11—C10—C15	117.2 (3)
H1B—C1—H1C	109.5	C11—C10—C9	120.9 (3)
C26—C1—H1D	109.5	C15—C10—C9	121.8 (3)
H1B—C1—H1D	109.5	C10—C11—C12	122.1 (3)
H1C—C1—H1D	109.5	C10—C11—H11A	119.0
C3—C2—H2B	109.5	C12—C11—H11A	119.0
C3—C2—H2C	109.5	C13—C12—C11	119.1 (3)
H2B—C2—H2C	109.5	C13—C12—H12A	120.4
C3—C2—H2D	109.5	C11—C12—H12A	120.4
H2B—C2—H2D	109.5	C14—C13—C12	119.7 (3)
H2C—C2—H2D	109.5	C14—C13—H13A	120.1
C2—C3—C4	115.5 (3)	C12—C13—H13A	120.1
C2—C3—H3A	108.4	C13—C14—C15	120.6 (3)
C4—C3—H3A	108.4	C13—C14—H14A	119.7
C2—C3—H3B	108.4	C15—C14—H14A	119.7
C4—C3—H3B	108.4	C14—C15—C10	121.1 (3)
H3A—C3—H3B	107.5	C14—C15—H15A	119.4
C5—C4—C3	128.1 (3)	C10—C15—H15A	119.4
C5—C4—C7	110.5 (3)	C22—C21—C26	121.1 (3)
C3—C4—C7	121.3 (3)	C22—C21—H21A	119.5
C4—C5—N	113.7 (3)	C26—C21—H21A	119.5
C4—C5—H5A	123.2	C23—C22—C21	119.7 (3)
N—C5—H5A	123.2	C23—C22—H22A	120.1
N—C6—C7	106.3 (3)	C21—C22—H22A	120.1
N—C6—H6A	110.5	C22—C23—C24	120.0 (3)
C7—C6—H6A	110.5	C22—C23—S1	121.0 (3)
N—C6—H6B	110.5	C24—C23—S1	118.6 (3)
C7—C6—H6B	110.5	C25—C24—C23	119.0 (3)
H6A—C6—H6B	108.7	C25—C24—H24A	120.5
C4—C7—C6	103.2 (3)	C23—C24—H24A	120.5
C4—C7—C8	113.6 (3)	C26—C25—C24	122.4 (3)
C6—C7—C8	114.3 (3)	C26—C25—H25A	118.8
C4—C7—H7A	108.5	C24—C25—H25A	118.8
C6—C7—H7A	108.5	C25—C26—C21	117.7 (3)
C8—C7—H7A	108.5	C25—C26—C1	121.6 (4)
C9—C8—C7	114.0 (3)	C21—C26—C1	120.6 (4)
C9—C8—H8A	108.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1^i	0.93	2.86	3.472 (4)	125
C12—H12A···O1^i	0.93	2.85	3.457 (5)	124
C2—H2D···O2^ii	0.96	2.94	3.818 (5)	153
C24—H24A···O2^ii	0.93	2.76	3.671 (4)	167
C13—H13A···O2^iii	0.93	2.99	3.542 (5)	120
C14—H14A···O2^iii	0.93	2.80	3.455 (4)	128

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