Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047800/zl2069sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047800/zl2069Isup2.hkl |
CCDC reference: 667291
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.131
- Data-to-parameter ratio = 19.8
checkCIF/PLATON results
No syntax errors found
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
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).
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.
All H-atoms were positioned geometrically and refined using a riding model with C—H=0.95 Å, Uiso(H)=1.2Ueq(C) for aromatic and C—H=0.96 Å, Uiso(H)=1.5Ueq(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.
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).
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).
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).
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) Å3 | Plate, colourless |
Z = 4 | 0.29 × 0.22 × 0.10 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.009P] where P = (Fo2 + 2Fc2)/3 |
2945 reflections | (Δ/σ)max < 0.001 |
149 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C14H15NO | V = 1184.8 (2) Å3 |
Mr = 213.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9476 (13) Å | µ = 0.08 mm−1 |
b = 7.4005 (6) Å | T = 293 K |
c = 14.8518 (14) Å | 0.29 × 0.22 × 0.10 mm |
β = 100.043 (6)° |
Bruker APEX CCD area-detector diffractometer | 2945 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 1461 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.993 | Rint = 0.035 |
8847 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.12 e Å−3 |
2945 reflections | Δρmin = −0.14 e Å−3 |
149 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.93 | 2.47 | 3.338 (2) | 155 |
C14—H14B···O1ii | 0.96 | 2.51 | 3.465 (2) | 172 |
Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H15NO |
Mr | 213.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.9476 (13), 7.4005 (6), 14.8518 (14) |
β (°) | 100.043 (6) |
V (Å3) | 1184.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.29 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2000) |
Tmin, Tmax | 0.984, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8847, 2945, 1461 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.131, 1.00 |
No. of reflections | 2945 |
No. of parameters | 149 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.93 | 2.47 | 3.338 (2) | 155 |
C14—H14B···O1ii | 0.96 | 2.51 | 3.465 (2) | 172 |
Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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).