1-(1-Tosyl-1H-pyrrol-2-yl)ethanone

In the mol­ecule of the title compound, C₁₃H₁₃NO₃S, the dihedral angle between the planar benzene and pyrrole rings is 101.7 (2)°. In the crystal structure, inter­molecular C—H...O hydrogen bonds link the mol­ecules into chains.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.053
• wR factor = 0.190
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C13

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, (I), is an intermediate of pyrrole derivatives, which widely exists in alkaloids and proteins in nature (Zhu et al., 1999), and of which, acetylpyrroles have potential use for electronic transport compounds containing anthrazoline unit by a reaction with diamine compounds, according to the literature reported recently (Tonzola et al., 2003). We here report its crystal structure, which is of interest to us in the field of electronic transport materials.

In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The rings A (C2—C7) and B (N/C8—C11) are, of course, and the dihedral angle between them is A/B = 101.7 (2)°.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains, in which they may be effective in the stabilization of the structure.

Related literature

For general backgroud, see: Tonzola et al. (2003); Allen et al. (1987). For related literature, see: Zhu et al. (1999); Hou et al. (1968).

S2. Experimental

The title compound, (I) was prepared by the literature method with a minor change (Hou et al., 1968). The crystals were obtained by dissolving (I) (1.5 g, 5.7 mmole) in a mixed solvent (48 ml) (chloroform/hexane, 1:5, v/v) and evaporating the solvent slowly at room temperature for about 7 d (m.p. 383 K).

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C), where x = 1.2 for aromatic H and x = 1.5 for methy H atoms.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines

1-(1-Tosyl-1H-pyrrol-2-yl)ethanone

Crystal data

C13H13NO3S	F(000) = 552
Mr = 263.30	Dx = 1.352 Mg m^−3
Monoclinic, P21/n	Melting point: 383 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.0123 (7) Å	Cell parameters from 25 reflections
b = 13.3199 (15) Å	θ = 10–13°
c = 12.5594 (12) Å	µ = 0.25 mm^−1
β = 105.15 (3)°	T = 298 K
V = 1293.8 (3) Å^3	Plate, colorless
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1845 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
Graphite monochromator	θmax = 26.0°, θmin = 2.3°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.907, Tmax = 0.952	l = −15→14
2700 measured reflections	3 standard reflections every 120 min
2518 independent reflections	intensity decay: none

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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.190	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.8P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2518 reflections	Δρmax = 0.30 e Å^−3
164 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.041 (6)

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
S	0.77713 (10)	0.18073 (7)	0.47420 (7)	0.0514 (3)
O1	0.9324 (3)	0.1618 (2)	0.5581 (2)	0.0711 (8)
O2	0.7475 (4)	0.13029 (19)	0.3715 (2)	0.0671 (8)
O3	0.4118 (4)	0.2119 (2)	0.3186 (2)	0.0798 (9)
N	0.6188 (3)	0.1493 (2)	0.5354 (2)	0.0461 (7)
C1	0.7224 (7)	0.6309 (3)	0.4173 (4)	0.0895 (15)
H1B	0.6951	0.6480	0.3404	0.134*
H1C	0.8315	0.6601	0.4546	0.134*
H1D	0.6338	0.6563	0.4488	0.134*
C2	0.7328 (5)	0.5177 (3)	0.4299 (3)	0.0617 (9)
C3	0.7721 (6)	0.4739 (3)	0.5338 (3)	0.0764 (12)
H3A	0.7889	0.5148	0.5957	0.092*
C4	0.7867 (5)	0.3715 (3)	0.5478 (3)	0.0651 (10)
H4A	0.8173	0.3435	0.6180	0.078*
C5	0.7548 (4)	0.3109 (2)	0.4547 (3)	0.0474 (8)
C6	0.7114 (5)	0.3523 (3)	0.3507 (3)	0.0542 (8)
H6A	0.6892	0.3110	0.2889	0.065*
C7	0.7010 (5)	0.4558 (3)	0.3384 (3)	0.0602 (9)
H7A	0.6725	0.4837	0.2681	0.072*
C8	0.6564 (5)	0.1250 (3)	0.6460 (3)	0.0594 (9)
H8A	0.7646	0.1291	0.6961	0.071*
C9	0.5095 (5)	0.0943 (3)	0.6688 (3)	0.0669 (10)
H9A	0.4994	0.0726	0.7372	0.080*
C10	0.3754 (5)	0.1005 (3)	0.5734 (3)	0.0559 (9)
H10A	0.2602	0.0847	0.5671	0.067*
C11	0.4420 (4)	0.1338 (2)	0.4903 (3)	0.0439 (7)
C12	0.3477 (4)	0.1621 (3)	0.3791 (3)	0.0535 (8)
C13	0.1630 (5)	0.1285 (4)	0.3391 (4)	0.0811 (13)
H13A	0.1156	0.1519	0.2650	0.122*
H13B	0.0972	0.1556	0.3862	0.122*
H13C	0.1581	0.0565	0.3404	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0462 (5)	0.0525 (5)	0.0606 (6)	0.0007 (4)	0.0232 (4)	0.0017 (4)
O1	0.0451 (14)	0.0790 (18)	0.090 (2)	0.0079 (12)	0.0182 (13)	0.0135 (15)
O2	0.0844 (19)	0.0576 (15)	0.0723 (17)	−0.0025 (13)	0.0434 (15)	−0.0103 (13)
O3	0.0692 (18)	0.106 (2)	0.0597 (16)	−0.0163 (16)	0.0082 (13)	0.0214 (16)
N	0.0429 (15)	0.0503 (15)	0.0468 (15)	−0.0030 (11)	0.0146 (12)	0.0036 (12)
C1	0.094 (3)	0.051 (2)	0.112 (4)	0.000 (2)	0.008 (3)	−0.003 (2)
C2	0.053 (2)	0.057 (2)	0.071 (2)	−0.0067 (16)	0.0079 (17)	−0.0059 (18)
C3	0.093 (3)	0.064 (2)	0.063 (2)	−0.007 (2)	0.004 (2)	−0.016 (2)
C4	0.079 (3)	0.065 (2)	0.0446 (19)	−0.0059 (19)	0.0052 (18)	0.0025 (17)
C5	0.0417 (16)	0.0511 (18)	0.0515 (18)	−0.0057 (14)	0.0161 (14)	0.0011 (15)
C6	0.060 (2)	0.059 (2)	0.0482 (18)	−0.0036 (16)	0.0225 (16)	−0.0015 (15)
C7	0.062 (2)	0.062 (2)	0.057 (2)	−0.0026 (17)	0.0168 (17)	0.0093 (17)
C8	0.057 (2)	0.069 (2)	0.0496 (19)	−0.0028 (17)	0.0098 (16)	0.0070 (17)
C9	0.073 (2)	0.082 (3)	0.050 (2)	−0.004 (2)	0.0243 (18)	0.0155 (19)
C10	0.0510 (19)	0.059 (2)	0.065 (2)	0.0000 (16)	0.0270 (17)	0.0059 (17)
C11	0.0408 (16)	0.0443 (16)	0.0480 (17)	0.0006 (13)	0.0141 (14)	−0.0007 (13)
C12	0.0494 (19)	0.059 (2)	0.0523 (19)	−0.0003 (15)	0.0132 (15)	−0.0039 (16)
C13	0.050 (2)	0.115 (4)	0.071 (3)	−0.002 (2)	0.0007 (19)	0.009 (3)

Geometric parameters (Å, º)

S—O2	1.418 (3)	C4—H4A	0.9300
S—O1	1.427 (3)	C5—C6	1.376 (5)
S—N	1.699 (3)	C6—C7	1.387 (5)
S—C5	1.754 (3)	C6—H6A	0.9300
O3—C12	1.220 (4)	C7—H7A	0.9300
N—C8	1.381 (4)	C8—C9	1.346 (5)
N—C11	1.396 (4)	C8—H8A	0.9300
C1—C2	1.515 (6)	C9—C10	1.387 (5)
C1—H1B	0.9600	C9—H9A	0.9300
C1—H1C	0.9600	C10—C11	1.363 (5)
C1—H1D	0.9600	C10—H10A	0.9300
C2—C7	1.384 (5)	C11—C12	1.453 (5)
C2—C3	1.389 (6)	C12—C13	1.501 (5)
C3—C4	1.376 (6)	C13—H13A	0.9600
C3—H3A	0.9300	C13—H13B	0.9600
C4—C5	1.387 (5)	C13—H13C	0.9600
O2—S—O1	119.63 (18)	C5—C6—C7	119.8 (3)
O2—S—N	109.10 (15)	C5—C6—H6A	120.1
O1—S—N	103.43 (15)	C7—C6—H6A	120.1
O2—S—C5	110.79 (16)	C2—C7—C6	120.5 (3)
O1—S—C5	108.38 (17)	C2—C7—H7A	119.8
N—S—C5	104.23 (14)	C6—C7—H7A	119.8
C8—N—C11	107.7 (3)	C9—C8—N	108.2 (3)
C8—N—S	121.4 (2)	C9—C8—H8A	125.9
C11—N—S	130.7 (2)	N—C8—H8A	125.9
C2—C1—H1B	109.5	C8—C9—C10	108.7 (3)
C2—C1—H1C	109.5	C8—C9—H9A	125.6
H1B—C1—H1C	109.5	C10—C9—H9A	125.6
C2—C1—H1D	109.5	C11—C10—C9	108.1 (3)
H1B—C1—H1D	109.5	C11—C10—H10A	125.9
H1C—C1—H1D	109.5	C9—C10—H10A	125.9
C7—C2—C3	118.5 (4)	C10—C11—N	107.2 (3)
C7—C2—C1	120.8 (4)	C10—C11—C12	127.6 (3)
C3—C2—C1	120.7 (4)	N—C11—C12	124.6 (3)
C4—C3—C2	121.8 (4)	O3—C12—C11	122.8 (3)
C4—C3—H3A	119.1	O3—C12—C13	119.5 (3)
C2—C3—H3A	119.1	C11—C12—C13	117.6 (3)
C3—C4—C5	118.6 (3)	C12—C13—H13A	109.5
C3—C4—H4A	120.7	C12—C13—H13B	109.5
C5—C4—H4A	120.7	H13A—C13—H13B	109.5
C6—C5—C4	120.8 (3)	C12—C13—H13C	109.5
C6—C5—S	121.3 (3)	H13A—C13—H13C	109.5
C4—C5—S	117.9 (3)	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3^i	0.93	2.54	3.468 (4)	173

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.