organic compounds
2-(4-Fluorophenyl)-1-(3-methoxyphenyl)-4,5-dimethyl-1H-imidazole
aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India, bDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, and cDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India
*Correspondence e-mail: raghema2000@yahoo.co.in
In the title compound, C18H17FN2O, the imidazole ring makes dihedral angles of 68.81 (6) and 25.20 (8)° with the methoxyphenyl and fluorophenyl rings, respectively. The dihedral angle between the methoxyphenyl and fluorophenyl ring is 71.89 (6)°. In the crystal, molecules are linked into inversion dimers with an R22(8) graph-set motif by pairs of weak C—H⋯F interactions.
CCDC reference: 974443
Related literature
For related structures, see: Rizwana Begum et al. (2013); Srinivasan et al. (2013); Gayathri et al. (2010); Rosepriya et al. (2011). For graph-set motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 974443
https://doi.org/10.1107/S1600536813032492/hg5365sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032492/hg5365Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813032492/hg5365Isup3.cml
To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), m-methoxy aniline (1.5 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 4-fluorobenzaldehyde (1.7 g, 15 mmol) was added about 1 h by maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by
using hexane: ethyl acetate as the Yield: 1.94 g (48%).All H atoms were placed in geometrically idealized positions (C—H = 0.93 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) but the methyl H atoms were located in SHELX with an ideal geometry (C—H = 0.96 Å) , Uiso(H) = 1.5Ueq(C).
In a continuation of structural studies of 4,5-dimethyl-1H-imidazole derivatives (Rizwana et al., 2013; Srinivasan et al., 2013; Gayathri et al., 2010; Rosepriya et al., 2011), we have taken up the title compound, (I), for crystallographic investigation.
In (I) (Fig. 1), C18H17FN2O, the imidazole ring is essentially planar and makes dihedral angles of 68.81 (6)° and 25.20 (8)° with the methoxyphenyl (C5-C10) and fluorophenyl rings (C13-C18) respectively. The dihedral angle between the methoxyphenyl and fluorophenyl ring is 71.89 (6)°. The C15—H15···F2 (-x,-y,-1 - z) interaction link pairs of molecules across centres of inversion to form dimers with ring motif R22(8) (Bernstein et al., (1995)) (Fig. 2).
For related structures, see: Rizwana Begum et al. (2013); Srinivasan et al. (2013); Gayathri et al. (2010); Rosepriya et al. (2011). For graph-set motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C18H17FN2O | Z = 2 |
Mr = 296.34 | F(000) = 312 |
Triclinic, P1 | Dx = 1.253 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1196 (5) Å | Cell parameters from 3597 reflections |
b = 9.6014 (6) Å | θ = 2.5–30.3° |
c = 10.6116 (6) Å | µ = 0.09 mm−1 |
α = 106.818 (3)° | T = 293 K |
β = 92.059 (3)° | Block, colourless |
γ = 96.114 (3)° | 0.30 × 0.30 × 0.25 mm |
V = 785.45 (8) Å3 |
Bruker Kappa APEXII CCD diffractometer | 3597 independent reflections |
Radiation source: fine-focus sealed tube | 2477 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω and φ scan | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→10 |
Tmin = 0.974, Tmax = 0.979 | k = −12→12 |
15949 measured reflections | l = −13→13 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.1414P] where P = (Fo2 + 2Fc2)/3 |
3597 reflections | (Δ/σ)max = 0.001 |
202 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C18H17FN2O | γ = 96.114 (3)° |
Mr = 296.34 | V = 785.45 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1196 (5) Å | Mo Kα radiation |
b = 9.6014 (6) Å | µ = 0.09 mm−1 |
c = 10.6116 (6) Å | T = 293 K |
α = 106.818 (3)° | 0.30 × 0.30 × 0.25 mm |
β = 92.059 (3)° |
Bruker Kappa APEXII CCD diffractometer | 3597 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2477 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.979 | Rint = 0.031 |
15949 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.20 e Å−3 |
3597 reflections | Δρmin = −0.22 e Å−3 |
202 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 | ||
C1 | 0.2524 (2) | 0.71718 (19) | 0.06251 (16) | 0.0606 (4) | |
C2 | 0.2395 (3) | 0.8699 (2) | 0.0606 (2) | 0.0941 (7) | |
H2A | 0.2741 | 0.9366 | 0.1462 | 0.141* | |
H2B | 0.1265 | 0.8791 | 0.0378 | 0.141* | |
H2C | 0.3096 | 0.8927 | −0.0035 | 0.141* | |
C3 | 0.2938 (2) | 0.66931 (18) | 0.16587 (15) | 0.0574 (4) | |
C4 | 0.3379 (3) | 0.7478 (2) | 0.30717 (17) | 0.0771 (5) | |
H4A | 0.3221 | 0.8491 | 0.3241 | 0.116* | |
H4B | 0.4521 | 0.7407 | 0.3284 | 0.116* | |
H4C | 0.2683 | 0.7046 | 0.3605 | 0.116* | |
C5 | 0.29393 (19) | 0.41950 (17) | 0.19342 (14) | 0.0504 (4) | |
C6 | 0.1516 (2) | 0.33657 (19) | 0.20825 (17) | 0.0597 (4) | |
H6 | 0.0503 | 0.3431 | 0.1679 | 0.072* | |
C7 | 0.1631 (2) | 0.2430 (2) | 0.2848 (2) | 0.0709 (5) | |
H7 | 0.0683 | 0.1851 | 0.2952 | 0.085* | |
C8 | 0.3106 (3) | 0.2339 (2) | 0.34526 (19) | 0.0705 (5) | |
H8 | 0.3157 | 0.1707 | 0.3968 | 0.085* | |
C9 | 0.4529 (2) | 0.3186 (2) | 0.33012 (15) | 0.0609 (4) | |
C10 | 0.4455 (2) | 0.41192 (18) | 0.25281 (14) | 0.0551 (4) | |
H10 | 0.5408 | 0.4684 | 0.2410 | 0.066* | |
C11 | 0.7407 (3) | 0.3921 (3) | 0.3874 (2) | 0.0872 (6) | |
H11A | 0.7659 | 0.3754 | 0.2969 | 0.131* | |
H11B | 0.8308 | 0.3691 | 0.4358 | 0.131* | |
H11C | 0.7252 | 0.4931 | 0.4250 | 0.131* | |
C12 | 0.23901 (18) | 0.48287 (17) | −0.01663 (14) | 0.0504 (4) | |
C13 | 0.22060 (19) | 0.33656 (18) | −0.11246 (14) | 0.0526 (4) | |
C14 | 0.1224 (2) | 0.3145 (2) | −0.22791 (17) | 0.0648 (5) | |
H14 | 0.0651 | 0.3896 | −0.2386 | 0.078* | |
C15 | 0.1082 (3) | 0.1840 (2) | −0.32662 (19) | 0.0757 (5) | |
H15 | 0.0429 | 0.1705 | −0.4041 | 0.091* | |
C16 | 0.1914 (3) | 0.0748 (2) | −0.30879 (19) | 0.0712 (5) | |
C17 | 0.2885 (3) | 0.0901 (2) | −0.1976 (2) | 0.0758 (5) | |
H17 | 0.3439 | 0.0135 | −0.1880 | 0.091* | |
C18 | 0.3031 (2) | 0.2221 (2) | −0.09918 (17) | 0.0662 (5) | |
H18 | 0.3696 | 0.2344 | −0.0226 | 0.079* | |
N1 | 0.21906 (17) | 0.60175 (15) | −0.05036 (12) | 0.0574 (4) | |
N2 | 0.28515 (16) | 0.51797 (14) | 0.11500 (12) | 0.0509 (3) | |
O1 | 0.59387 (18) | 0.30194 (18) | 0.39395 (14) | 0.0866 (4) | |
F2 | 0.17789 (18) | −0.05430 (14) | −0.40697 (13) | 0.1043 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0682 (11) | 0.0603 (10) | 0.0551 (9) | 0.0035 (8) | 0.0008 (7) | 0.0217 (8) |
C2 | 0.138 (2) | 0.0661 (12) | 0.0821 (14) | 0.0073 (12) | −0.0133 (13) | 0.0318 (11) |
C3 | 0.0622 (10) | 0.0604 (10) | 0.0495 (8) | 0.0004 (7) | 0.0018 (7) | 0.0189 (7) |
C4 | 0.1045 (15) | 0.0707 (12) | 0.0521 (10) | 0.0007 (10) | −0.0037 (9) | 0.0166 (9) |
C5 | 0.0560 (9) | 0.0580 (9) | 0.0406 (7) | 0.0081 (7) | 0.0066 (6) | 0.0193 (7) |
C6 | 0.0564 (9) | 0.0641 (10) | 0.0604 (9) | 0.0043 (7) | 0.0071 (7) | 0.0220 (8) |
C7 | 0.0715 (12) | 0.0672 (11) | 0.0807 (12) | −0.0006 (9) | 0.0158 (9) | 0.0342 (10) |
C8 | 0.0898 (14) | 0.0664 (11) | 0.0691 (11) | 0.0158 (10) | 0.0175 (10) | 0.0377 (9) |
C9 | 0.0691 (11) | 0.0733 (11) | 0.0482 (8) | 0.0194 (9) | 0.0073 (7) | 0.0260 (8) |
C10 | 0.0549 (9) | 0.0699 (10) | 0.0460 (8) | 0.0071 (7) | 0.0062 (6) | 0.0255 (7) |
C11 | 0.0686 (13) | 0.1295 (19) | 0.0757 (13) | 0.0226 (12) | −0.0032 (10) | 0.0468 (13) |
C12 | 0.0480 (8) | 0.0630 (9) | 0.0450 (8) | 0.0069 (7) | 0.0037 (6) | 0.0230 (7) |
C13 | 0.0505 (8) | 0.0642 (10) | 0.0463 (8) | 0.0052 (7) | 0.0073 (6) | 0.0215 (7) |
C14 | 0.0676 (11) | 0.0681 (11) | 0.0582 (10) | 0.0073 (8) | −0.0056 (8) | 0.0196 (8) |
C15 | 0.0791 (13) | 0.0805 (13) | 0.0592 (11) | 0.0014 (10) | −0.0100 (9) | 0.0122 (10) |
C16 | 0.0795 (13) | 0.0648 (11) | 0.0614 (11) | 0.0019 (9) | 0.0099 (9) | 0.0081 (9) |
C17 | 0.0929 (14) | 0.0700 (12) | 0.0691 (12) | 0.0250 (10) | 0.0141 (10) | 0.0212 (10) |
C18 | 0.0733 (11) | 0.0773 (12) | 0.0516 (9) | 0.0212 (9) | 0.0039 (8) | 0.0205 (9) |
N1 | 0.0623 (8) | 0.0642 (8) | 0.0497 (7) | 0.0067 (6) | 0.0007 (6) | 0.0241 (7) |
N2 | 0.0523 (7) | 0.0595 (8) | 0.0446 (6) | 0.0049 (6) | 0.0026 (5) | 0.0222 (6) |
O1 | 0.0781 (9) | 0.1210 (12) | 0.0843 (9) | 0.0234 (8) | −0.0001 (7) | 0.0640 (9) |
F2 | 0.1274 (11) | 0.0784 (8) | 0.0861 (9) | 0.0117 (7) | 0.0010 (7) | −0.0073 (7) |
C1—C3 | 1.351 (2) | C9—C10 | 1.383 (2) |
C1—N1 | 1.371 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.488 (3) | C11—O1 | 1.413 (3) |
C2—H2A | 0.9600 | C11—H11A | 0.9600 |
C2—H2B | 0.9600 | C11—H11B | 0.9600 |
C2—H2C | 0.9600 | C11—H11C | 0.9600 |
C3—N2 | 1.389 (2) | C12—N1 | 1.3149 (19) |
C3—C4 | 1.481 (2) | C12—N2 | 1.3667 (18) |
C4—H4A | 0.9600 | C12—C13 | 1.465 (2) |
C4—H4B | 0.9600 | C13—C18 | 1.384 (2) |
C4—H4C | 0.9600 | C13—C14 | 1.388 (2) |
C5—C6 | 1.372 (2) | C14—C15 | 1.372 (3) |
C5—C10 | 1.381 (2) | C14—H14 | 0.9300 |
C5—N2 | 1.4342 (18) | C15—C16 | 1.360 (3) |
C6—C7 | 1.382 (2) | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—C17 | 1.357 (3) |
C7—C8 | 1.361 (3) | C16—F2 | 1.360 (2) |
C7—H7 | 0.9300 | C17—C18 | 1.380 (3) |
C8—C9 | 1.382 (3) | C17—H17 | 0.9300 |
C8—H8 | 0.9300 | C18—H18 | 0.9300 |
C9—O1 | 1.357 (2) | ||
C3—C1—N1 | 110.58 (15) | C5—C10—H10 | 120.7 |
C3—C1—C2 | 128.58 (17) | C9—C10—H10 | 120.7 |
N1—C1—C2 | 120.83 (15) | O1—C11—H11A | 109.5 |
C1—C2—H2A | 109.5 | O1—C11—H11B | 109.5 |
C1—C2—H2B | 109.5 | H11A—C11—H11B | 109.5 |
H2A—C2—H2B | 109.5 | O1—C11—H11C | 109.5 |
C1—C2—H2C | 109.5 | H11A—C11—H11C | 109.5 |
H2A—C2—H2C | 109.5 | H11B—C11—H11C | 109.5 |
H2B—C2—H2C | 109.5 | N1—C12—N2 | 110.49 (14) |
C1—C3—N2 | 105.43 (14) | N1—C12—C13 | 122.62 (13) |
C1—C3—C4 | 131.90 (17) | N2—C12—C13 | 126.82 (13) |
N2—C3—C4 | 122.66 (14) | C18—C13—C14 | 117.93 (16) |
C3—C4—H4A | 109.5 | C18—C13—C12 | 124.26 (14) |
C3—C4—H4B | 109.5 | C14—C13—C12 | 117.67 (14) |
H4A—C4—H4B | 109.5 | C15—C14—C13 | 121.29 (17) |
C3—C4—H4C | 109.5 | C15—C14—H14 | 119.4 |
H4A—C4—H4C | 109.5 | C13—C14—H14 | 119.4 |
H4B—C4—H4C | 109.5 | C16—C15—C14 | 118.56 (17) |
C6—C5—C10 | 121.91 (14) | C16—C15—H15 | 120.7 |
C6—C5—N2 | 119.19 (14) | C14—C15—H15 | 120.7 |
C10—C5—N2 | 118.89 (14) | C17—C16—C15 | 122.62 (18) |
C5—C6—C7 | 118.12 (16) | C17—C16—F2 | 118.87 (18) |
C5—C6—H6 | 120.9 | C15—C16—F2 | 118.51 (18) |
C7—C6—H6 | 120.9 | C16—C17—C18 | 118.46 (18) |
C8—C7—C6 | 121.27 (17) | C16—C17—H17 | 120.8 |
C8—C7—H7 | 119.4 | C18—C17—H17 | 120.8 |
C6—C7—H7 | 119.4 | C17—C18—C13 | 121.13 (17) |
C7—C8—C9 | 120.05 (16) | C17—C18—H18 | 119.4 |
C7—C8—H8 | 120.0 | C13—C18—H18 | 119.4 |
C9—C8—H8 | 120.0 | C12—N1—C1 | 106.37 (13) |
O1—C9—C8 | 115.78 (15) | C12—N2—C3 | 107.12 (12) |
O1—C9—C10 | 124.26 (16) | C12—N2—C5 | 127.45 (13) |
C8—C9—C10 | 119.96 (16) | C3—N2—C5 | 124.53 (12) |
C5—C10—C9 | 118.68 (15) | C9—O1—C11 | 117.83 (14) |
N1—C1—C3—N2 | −0.23 (19) | C15—C16—C17—C18 | −0.1 (3) |
C2—C1—C3—N2 | 179.2 (2) | F2—C16—C17—C18 | 179.23 (17) |
N1—C1—C3—C4 | −179.06 (18) | C16—C17—C18—C13 | 0.3 (3) |
C2—C1—C3—C4 | 0.4 (4) | C14—C13—C18—C17 | 0.1 (3) |
C10—C5—C6—C7 | −0.3 (2) | C12—C13—C18—C17 | −175.54 (16) |
N2—C5—C6—C7 | −179.69 (15) | N2—C12—N1—C1 | −0.27 (17) |
C5—C6—C7—C8 | 0.7 (3) | C13—C12—N1—C1 | −177.54 (14) |
C6—C7—C8—C9 | −0.4 (3) | C3—C1—N1—C12 | 0.32 (19) |
C7—C8—C9—O1 | −179.92 (17) | C2—C1—N1—C12 | −179.21 (18) |
C7—C8—C9—C10 | −0.4 (3) | N1—C12—N2—C3 | 0.13 (17) |
C6—C5—C10—C9 | −0.5 (2) | C13—C12—N2—C3 | 177.25 (14) |
N2—C5—C10—C9 | 178.94 (14) | N1—C12—N2—C5 | 169.55 (14) |
O1—C9—C10—C5 | −179.70 (15) | C13—C12—N2—C5 | −13.3 (2) |
C8—C9—C10—C5 | 0.8 (2) | C1—C3—N2—C12 | 0.07 (17) |
N1—C12—C13—C18 | 151.38 (16) | C4—C3—N2—C12 | 179.02 (16) |
N2—C12—C13—C18 | −25.4 (2) | C1—C3—N2—C5 | −169.74 (15) |
N1—C12—C13—C14 | −24.2 (2) | C4—C3—N2—C5 | 9.2 (2) |
N2—C12—C13—C14 | 158.97 (15) | C6—C5—N2—C12 | −62.4 (2) |
C18—C13—C14—C15 | −0.5 (3) | C10—C5—N2—C12 | 118.14 (17) |
C12—C13—C14—C15 | 175.38 (16) | C6—C5—N2—C3 | 105.29 (18) |
C13—C14—C15—C16 | 0.7 (3) | C10—C5—N2—C3 | −74.2 (2) |
C14—C15—C16—C17 | −0.3 (3) | C8—C9—O1—C11 | −176.56 (17) |
C14—C15—C16—F2 | −179.68 (17) | C10—C9—O1—C11 | 3.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···F2i | 0.93 | 2.55 | 3.437 (2) | 160 |
Symmetry code: (i) −x, −y, −z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···F2i | 0.93 | 2.55 | 3.437 (2) | 159.6 |
Symmetry code: (i) −x, −y, −z−1. |
Acknowledgements
SR thanks the University Grants Commission for financial support of this work (grant MRP-4335/12). The authors are thankful to the SAIF, IIT Madras, for the data collection.
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Srinivasan, N., Rizwana Begum, S. R. A., Hema, R., Sridhar, B. & Anitha, A. G. (2013). Acta Cryst. E69, o1599–o1600. CSD CrossRef CAS IUCr Journals Google Scholar
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In a continuation of structural studies of 4,5-dimethyl-1H-imidazole derivatives (Rizwana et al., 2013; Srinivasan et al., 2013; Gayathri et al., 2010; Rosepriya et al., 2011), we have taken up the title compound, (I), for crystallographic investigation.
In (I) (Fig. 1), C18H17FN2O, the imidazole ring is essentially planar and makes dihedral angles of 68.81 (6)° and 25.20 (8)° with the methoxyphenyl (C5-C10) and fluorophenyl rings (C13-C18) respectively. The dihedral angle between the methoxyphenyl and fluorophenyl ring is 71.89 (6)°. The C15—H15···F2 (-x,-y,-1 - z) interaction link pairs of molecules across centres of inversion to form dimers with ring motif R22(8) (Bernstein et al., (1995)) (Fig. 2).