1-(4-Acetyl­phen­yl)-2,5-dimethyl-1H-pyrrole

In the title compound, C₁₄H₁₅NO, the mol­ecules are joined via C—H...O inter­actions into chains along the b axis. The planes of the pyrrole and benzene rings are at an angle of 62.17 (10)° with respect to each other.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.131
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

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Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   0 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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S1. Comment

Pyrroles are important compounds in the fields of macromolecular, environmental and medical chemistry, optics and nano-technologies (Kaianak, 1998; Dutta & De, 2006; Stejskal et al., 2004; Bonfiglio et al., 1998; Biagiotti et al., 2007; Zanganeh & Amini, 2007; Anzenbacher et al., 2006). For many applications pyrroles have to be able to be polymerized electrochemically and therefore a better understanding of the kinetic and thermodynamic polymerization parameters is needed (Wang et al., 2001). Such parameters are affected by the acid/base characteristics of the nitrogen atom and the α and β positions, characteristics that have been determined with the help of many N-phenyl substituted pyrroles. (Wang et al., 2001). The title compound (Fig. 1), obtained by the Paal-Knorr method (Gerrius, 1990), is such a N-phenyl substituted pyrrole. In each molecule the non H-atoms are distributed over two planes: the pyrrolic and the benzene phenyl ring plane. The atoms O1 and C14 are located basically within the mean plane of the six-membered aromatic ring with deviations of only 0.158 (1) and 0.113 (2) Å. The dihedral angle between the two planes is 62.2 (1)°. Due to the lack of conventional donors there are no conventional hydrogen bonds between the molecules. However, intermolecular interactions of the type C—H···O join the molecules in chains that run along the b axis (Fig. 2).

Related literature

For the use of polypyrroles as sensors, see: Anzenbacher et al. (2006); Zanganeh & Amini (2007). For investigations of other polypyrrole properties, see: Biagiotti et al. (2007); Bonfiglio et al. (1998); Dutta & De (2006); Kaianak (1998); Stejskal et al. (2004); Wang et al. (2001). For the synthesis of the title compound, see: Gerrius (1990); Banik et al. (2004).

S2. Experimental

2,5-Dimethyl-1-(4-acetophenyl)-1H-pyrrole was synthesized by the method of Paal-Knorr (Gerrius, 1990) in an way analogous to that described by Banik (Banik et al., 2004) using iodine as catalyst.

S3. Refinement

All H-atoms were positioned geometrically and refined using a riding model with C—H=0.95 Å, U_iso(H)=1.2U_eq(C) for aromatic and C—H=0.96 Å, U_iso(H)=1.5U_eq(C) for the methyl groups. The methyl groups were idealized based on difference electron density synthesis, then refined as a rigid group allowed to rotate but not tip.

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. Packing diagram of the title compound. C—H···O interactions are shown as dashed lines.
	Fig. 3. One of the chains in which the molecules aggregate via C—H···O intermolecular interactions.

1-(4-Acetylphenyl)-2,5-dimethyl-1H-pyrrole

Crystal data

C14H15NO	F(000) = 456
Mr = 213.27	Dx = 1.196 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.9476 (13) Å	Cell parameters from 1357 reflections
b = 7.4005 (6) Å	θ = 2.8–22.2°
c = 14.8518 (14) Å	µ = 0.08 mm^−1
β = 100.043 (6)°	T = 293 K
V = 1184.8 (2) Å^3	Plate, colourless
Z = 4	0.29 × 0.22 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2945 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→14
Tmin = 0.984, Tmax = 0.993	k = −8→9
8847 measured reflections	l = −19→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 0.009P] where P = (Fo^2 + 2Fc^2)/3
2945 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.14 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.

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
O1	0.02792 (13)	−0.15368 (19)	0.36051 (9)	0.0795 (4)
N1	0.31347 (12)	0.52600 (19)	0.56347 (9)	0.0533 (4)
C1	0.37686 (15)	0.6603 (2)	0.52528 (12)	0.0557 (5)
C2	0.43942 (17)	0.7583 (3)	0.59568 (13)	0.0686 (5)
H2	0.4906	0.8567	0.5905	0.082*
C3	0.41374 (17)	0.6856 (3)	0.67830 (13)	0.0709 (6)
H3	0.4447	0.7284	0.7367	0.085*
C4	0.33637 (16)	0.5430 (3)	0.65807 (12)	0.0598 (5)
C5	0.37593 (17)	0.6748 (3)	0.42511 (12)	0.0690 (5)
H5A	0.4332	0.7669	0.4139	0.103*
H5B	0.2940	0.7057	0.3945	0.103*
H5C	0.4000	0.5612	0.4024	0.103*
C6	0.27643 (18)	0.4236 (3)	0.71888 (13)	0.0768 (6)
H6A	0.3174	0.3084	0.7248	0.115*
H6B	0.1906	0.4071	0.6928	0.115*
H6C	0.2828	0.4785	0.7781	0.115*
C7	0.23376 (15)	0.3954 (2)	0.51268 (11)	0.0498 (4)
C8	0.25979 (16)	0.2123 (3)	0.52272 (12)	0.0571 (5)
H8	0.3294	0.1734	0.5632	0.069*
C9	0.18239 (15)	0.0885 (2)	0.47270 (12)	0.0563 (5)
H9	0.2006	−0.0339	0.4797	0.068*
C10	0.07785 (15)	0.1421 (2)	0.41203 (10)	0.0484 (4)
C11	0.05271 (15)	0.3253 (2)	0.40330 (11)	0.0566 (5)
H11	−0.0173	0.3642	0.3632	0.068*
C12	0.12968 (15)	0.4513 (2)	0.45298 (11)	0.0560 (5)
H12	0.1114	0.5738	0.4462	0.067*
C13	−0.00238 (17)	0.0043 (3)	0.35785 (11)	0.0563 (5)
C14	−0.12147 (16)	0.0631 (3)	0.30037 (13)	0.0713 (6)
H14A	−0.1657	−0.0409	0.2731	0.107*
H14B	−0.1042	0.1428	0.2531	0.107*
H14C	−0.1711	0.1252	0.3379	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0932 (10)	0.0530 (9)	0.0885 (10)	0.0083 (8)	0.0056 (8)	−0.0106 (7)
N1	0.0544 (8)	0.0552 (9)	0.0492 (8)	0.0022 (7)	0.0064 (6)	0.0009 (7)
C1	0.0548 (10)	0.0524 (11)	0.0596 (11)	0.0059 (9)	0.0092 (9)	0.0057 (9)
C2	0.0651 (12)	0.0636 (13)	0.0757 (14)	−0.0036 (10)	0.0079 (10)	−0.0033 (11)
C3	0.0683 (12)	0.0824 (15)	0.0596 (12)	−0.0050 (12)	0.0050 (10)	−0.0136 (11)
C4	0.0558 (10)	0.0724 (14)	0.0503 (10)	0.0060 (10)	0.0070 (8)	−0.0021 (9)
C5	0.0699 (12)	0.0733 (14)	0.0652 (12)	0.0011 (11)	0.0156 (10)	0.0100 (10)
C6	0.0792 (13)	0.0970 (16)	0.0543 (11)	−0.0027 (12)	0.0122 (10)	0.0058 (11)
C7	0.0528 (10)	0.0504 (11)	0.0472 (9)	0.0053 (9)	0.0116 (8)	0.0006 (8)
C8	0.0543 (10)	0.0583 (13)	0.0564 (10)	0.0128 (9)	0.0033 (8)	0.0064 (9)
C9	0.0626 (10)	0.0493 (11)	0.0572 (10)	0.0122 (9)	0.0110 (9)	0.0025 (9)
C10	0.0547 (10)	0.0493 (11)	0.0423 (9)	0.0079 (8)	0.0117 (8)	0.0027 (8)
C11	0.0557 (10)	0.0553 (12)	0.0555 (10)	0.0092 (9)	0.0001 (8)	0.0054 (9)
C12	0.0600 (10)	0.0465 (11)	0.0592 (11)	0.0108 (9)	0.0037 (9)	0.0043 (9)
C13	0.0681 (11)	0.0545 (12)	0.0487 (10)	0.0028 (10)	0.0173 (9)	0.0023 (9)
C14	0.0754 (13)	0.0674 (15)	0.0659 (12)	−0.0088 (11)	−0.0025 (10)	0.0052 (10)

Geometric parameters (Å, º)

O1—C13	1.214 (2)	C6—H6C	0.9600
N1—C1	1.389 (2)	C7—C12	1.380 (2)
N1—C4	1.389 (2)	C7—C8	1.387 (2)
N1—C7	1.427 (2)	C8—C9	1.375 (2)
C1—C2	1.356 (2)	C8—H8	0.9300
C1—C5	1.490 (2)	C9—C10	1.385 (2)
C2—C3	1.412 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.385 (2)
C3—C4	1.353 (2)	C10—C13	1.487 (2)
C3—H3	0.9300	C11—C12	1.381 (2)
C4—C6	1.495 (3)	C11—H11	0.9300
C5—H5A	0.9600	C12—H12	0.9300
C5—H5B	0.9600	C13—C14	1.493 (2)
C5—H5C	0.9600	C14—H14A	0.9600
C6—H6A	0.9600	C14—H14B	0.9600
C6—H6B	0.9600	C14—H14C	0.9600
C1—N1—C4	109.47 (15)	C12—C7—C8	119.55 (17)
C1—N1—C7	124.90 (14)	C12—C7—N1	119.81 (16)
C4—N1—C7	125.60 (14)	C8—C7—N1	120.64 (15)
C2—C1—N1	106.80 (16)	C9—C8—C7	119.81 (16)
C2—C1—C5	130.24 (17)	C9—C8—H8	120.1
N1—C1—C5	122.86 (16)	C7—C8—H8	120.1
C1—C2—C3	108.41 (18)	C8—C9—C10	121.48 (17)
C1—C2—H2	125.8	C8—C9—H9	119.3
C3—C2—H2	125.8	C10—C9—H9	119.3
C4—C3—C2	108.41 (17)	C11—C10—C9	117.98 (17)
C4—C3—H3	125.8	C11—C10—C13	122.10 (16)
C2—C3—H3	125.8	C9—C10—C13	119.92 (16)
C3—C4—N1	106.91 (16)	C12—C11—C10	121.20 (16)
C3—C4—C6	130.57 (17)	C12—C11—H11	119.4
N1—C4—C6	122.46 (17)	C10—C11—H11	119.4
C1—C5—H5A	109.5	C7—C12—C11	119.97 (16)
C1—C5—H5B	109.5	C7—C12—H12	120.0
H5A—C5—H5B	109.5	C11—C12—H12	120.0
C1—C5—H5C	109.5	O1—C13—C10	120.68 (17)
H5A—C5—H5C	109.5	O1—C13—C14	120.36 (18)
H5B—C5—H5C	109.5	C10—C13—C14	118.96 (17)
C4—C6—H6A	109.5	C13—C14—H14A	109.5
C4—C6—H6B	109.5	C13—C14—H14B	109.5
H6A—C6—H6B	109.5	H14A—C14—H14B	109.5
C4—C6—H6C	109.5	C13—C14—H14C	109.5
H6A—C6—H6C	109.5	H14A—C14—H14C	109.5
H6B—C6—H6C	109.5	H14B—C14—H14C	109.5
C4—N1—C1—C2	0.61 (18)	C4—N1—C7—C8	−63.3 (2)
C7—N1—C1—C2	178.52 (15)	C12—C7—C8—C9	0.5 (2)
C4—N1—C1—C5	177.38 (15)	N1—C7—C8—C9	−179.52 (14)
C7—N1—C1—C5	−4.7 (2)	C7—C8—C9—C10	−0.1 (2)
N1—C1—C2—C3	−0.6 (2)	C8—C9—C10—C11	−0.3 (2)
C5—C1—C2—C3	−177.04 (17)	C8—C9—C10—C13	178.87 (14)
C1—C2—C3—C4	0.4 (2)	C9—C10—C11—C12	0.4 (2)
C2—C3—C4—N1	0.0 (2)	C13—C10—C11—C12	−178.77 (14)
C2—C3—C4—C6	−177.10 (18)	C8—C7—C12—C11	−0.4 (2)
C1—N1—C4—C3	−0.38 (18)	N1—C7—C12—C11	179.61 (14)
C7—N1—C4—C3	−178.27 (15)	C10—C11—C12—C7	−0.1 (2)
C1—N1—C4—C6	177.01 (16)	C11—C10—C13—O1	173.12 (16)
C7—N1—C4—C6	−0.9 (3)	C9—C10—C13—O1	−6.0 (2)
C1—N1—C7—C12	−60.9 (2)	C11—C10—C13—C14	−7.2 (2)
C4—N1—C7—C12	116.66 (18)	C9—C10—C13—C14	173.60 (15)
C1—N1—C7—C8	119.11 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1^i	0.93	2.47	3.338 (2)	155
C14—H14B···O1^ii	0.96	2.51	3.465 (2)	172

Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+1/2.