Two 1-phenyl-1H-imidazoles, 4-(1H-imidazol-1-yl)benzaldehyde and 1-(4-methoxyphenyl)-1H-imidazole, differ in the substituent para to the imidazole group on the arene ring. Both molecules pack with different motifs via similar weak C—H⋯N/O interactions and differ with respect to the angles between the mean planes of the imidazole and arene rings.
Keywords: crystal structure, 1-phenyl-1H-imidazole derivatives, weak intermolecular interactions, non-centrosymmetric space group
Abstract
The title compounds, C10H8N2O, (I), and C10H10N2O, (II), are two 1-phenyl-1H-imidazole derivatives, which differ in the substituent para to the imidazole group on the arene ring, i.e. a benzaldehyde, (I), and an anisole, (II). Both molecules pack with different motifs via similar weak C—H⋯N/O interactions and differ with respect to the angles between the mean planes of the imidazole and arene rings [24.58 (7)° in (I) and 43.67 (4)° in (II)].
1. Chemical context
N-Arylated imidazoles are commonly found in the structures of an array of biologically active compounds (Ananthu et al., 2021 ▸). They have a variety of applications in the medicinal chemistry field, such as use in anticancer and anti-inflammatory medications and as antiviral agents (Shalini et al., 2010 ▸). They are also used in agriculture as fungicides, herbicides, and plant-growth regulators (Emel’yanenko et al., 2017 ▸). 4-(1H-Imidazol-1-yl)benzaldehyde, (I), may be synthesized in high yield by treating 4-bromobenzaldehyde with imidazole in an aprotic solvent with the addition of potassium carbonate and a copper(I) catalyst (Xi et al., 2008 ▸). The yellow solid is a common reagent in the synthesis of various targets with antifungal and antibacterial activity. It has been shown that (I) could be used to synthesize a series of 3-[4-(1H-imidazol-1-yl)phenyl]prop-2-en-1-ones with antifungal, antioxidant, and antileishmanial activities (Hussain et al., 2009 ▸). Cream-colored 1-(4-methoxyphenyl)-1H-imidazole, (II), and other similar compounds have been found to work as catalysts in the catalytic epoxidation of olefins with moderate to good yields using mild reaction conditions (Schröder et al., 2009 ▸). Compound (II) can be synthesized in a 99% isolated yield by allowing imidazole and 4-iodoanisole to react in acetonitrile in the presence of cesium carbonate and a copper(II) catalyst (Milenković et al., 2019 ▸).
2. Structural commentary
The molecular structures of the benzaldehyde derivative (I) (Fig. 1 ▸) and the anisole derivative (II) (Fig. 2 ▸) show the para nature of the substituent with respect to the imidazole group. The angle between the mean planes of the imidazole and arene rings is 24.58 (7)° in (I) and 43.67 (4)° in (II).
Figure 1.
A view of 4-(1H-imidazol-1-yl)benzaldehyde, (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2.
A view of 1-(4-methoxyphenyl)-1H-imidazole, (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
3. Supramolecular features
The molecules of benzaldehyde derivative (I) are held together in the solid state via weak C—H⋯O/N interactions (Fig. 3 ▸ and Table 1 ▸). Specifically, imidazole C—H groups interact with neighboring benzaldehyde O atoms (C8—H8A⋯O1i) and imidazole N atoms (C10—H10A⋯N2ii). The molecules also stack with an offset face-to-face geometrical arrangement of the arene rings, with an intermolecular centroid-to-centroid distance of 3.7749 (2) Å, a plane-to-centroid distance of 3.5002 (10) Å, and a ring shift of 1.414 (3) Å. Fig. 3 ▸ displays a di-periodic sheet with a thickness roughly equivalent to the length of the c axis, where the imidazoles interact in the interior and the aldehyde substituents extend to the faces. The sheets then stack in the [001] direction. Notably, (I) crystallizes in the space group P21 and is therefore a polar material in the solid state. Polar organic materials formed by achiral molecules are of interest in crystal engineering, in particular for nonlinear optical materials (Merritt & Tanski, 2018 ▸).
Figure 3.
A view of the molecular packing in 4-(1H-imidazol-1-yl)benzaldehyde, (I). [Symmetry codes: (i) x − 1, y − 1, z; (ii) −x + 1, y +
, −z + 1.]
Table 1. Hydrogen-bond geometry (Å, °) for (I) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C8—H8A⋯O1i | 0.95 | 2.51 | 3.458 (2) | 176 |
| C10—H10A⋯N2ii | 0.95 | 2.51 | 3.449 (2) | 173 |
Symmetry codes: (i)
; (ii)
.
Similarly, the molecules of anisole derivative (II) are held together in the solid state via weak C—H⋯O/N interactions (Fig. 4 ▸ and Table 2 ▸), with the same imidazole C—H groups as (I) interacting with a neighboring anisole O atom (C9—H9A⋯O1ii) and an imidazole N atom (C10—H10A⋯N2iii). A third weak interaction links the remaining imidazole H atom with the imidazole N atom (C8—H8A⋯N2i). Unlike benzaldehyde derivative (I), anisole derivative (II) does not exhibit any π-stacking geometrical arrangement of the arene rings and the molecules pack centrosymmetrically (Fig. 5 ▸).
Figure 4.
A view of the intermolecular interactions in 1-(4-methoxyphenyl)-1H-imidazole, (II). [Symmetry codes: (i) x, −y +
, z +
; (ii) x − 1, −y +
, z −
; (iii) −x + 1, −y + 1, −z.]
Table 2. Hydrogen-bond geometry (Å, °) for (II) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C8—H8A⋯N2i | 0.95 | 2.55 | 3.4391 (11) | 157 |
| C9—H9A⋯O1ii | 0.95 | 2.56 | 3.3048 (11) | 136 |
| C10—H10A⋯N2iii | 0.95 | 2.52 | 3.3004 (11) | 140 |
Symmetry codes: (i)
; (ii)
; (iii)
.
Figure 5.
A view of the molecular packing in 1-(4-methoxyphenyl)-1H-imidazole, (II).
4. Database survey
The Cambridge Structural Database (CSD; Groom et al., 2016 ▸) contains six simple para-X-substituted 1-phenyl-1H-imidazole derivatives: X = –NH2 (CSD refcode MUFCAS; Liang et al., 2009 ▸), –Br (PAJDUD; Ding et al., 2021 ▸), –I (FIQFUJ; Bejan et al., 2018 ▸), –CO2H (IKAWAT; Zheng et al., 2011 ▸), –CO2CH3 (BEMVUN; Khattri et al., 2016 ▸) and –COCH3 (XECDUG; Ibrahim et al., 2012 ▸). The amino and carboxylic acid derivatives engage in intermolecular hydrogen bonding with the imidazole N atom and exhibit angles between the mean planes of the imidazole and arene rings of 31.17 (MUFCAS) and 14.51° (IKAWAT). The halide derivatives both contain halide to imidazole nitrogen intermolecular contacts and angles between the mean planes of the imidazole and arene rings of 35.22 (PAJDUD) and 27.10° (FIQFUJ). Similar to the title compounds (I) and (II), the methyl ester and methyl ketone derivatives pack via weak C—H⋯N/O interactions and with angles between the mean planes of the imidazole and arene rings of 24.83 (BEMVUN) and 1.04° (XECDUG). In XECDUG, a molecule of water hydrogen bonds to the 1H-imidazole H and ortho-phenyl H of a neighboring molecule, holding the planes of the imidazole and arene rings nearly coplanar. Inspection of the bond lengths of the imidazole ring for all eight derivatives reveals that they are remarkably similar.
5. Synthesis and crystallization
4-(1H-Imidazol-1-yl)benzaldehyde (98%), (I), and 1-(4-methoxyphenyl)-1H-imidazole (98%), (II), were purchased from Aldrich Chemical Company, USA, and were used as received.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. H atoms on C atoms were included in calculated positions and refined using a riding model, with C—H = 0.95 Å and U iso(H) = 1.2U eq(C) for aryl H atoms, and C—H = 0.98 Å and U iso(H) = 1.5U eq(C) for methyl H atoms.
Table 3. Experimental details.
Experiments were carried out at 125 K using a Bruker APEXII CCD diffractometer. Absorption was corrected for by multi-scan methods (SADABS; Bruker, 2016 ▸). Refinement was on 119 parameters. H-atom parameters were constrained.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C10H8N2O | C10H10N2O |
| M r | 172.18 | 174.20 |
| Crystal system, space group | Monoclinic, P21 | Monoclinic, P21/c |
| a, b, c (Å) | 3.7749 (2), 7.3711 (5), 14.4524 (9) | 8.5663 (12), 11.2143 (16), 9.1635 (13) |
| β (°) | 91.096 (2) | 94.448 (2) |
| V (Å3) | 402.07 (4) | 877.6 (2) |
| Z | 2 | 4 |
| Radiation type | Cu Kα | Mo Kα |
| μ (mm−1) | 0.77 | 0.09 |
| Crystal size (mm) | 0.37 × 0.20 × 0.05 | 0.40 × 0.25 × 0.15 |
| Data collection | ||
| T min, T max | 0.80, 0.96 | 0.92, 0.99 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 5673, 1482, 1466 | 21397, 2678, 2332 |
| R int | 0.029 | 0.031 |
| (sin θ/λ)max (Å−1) | 0.615 | 0.715 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.027, 0.079, 1.14 | 0.040, 0.119, 1.04 |
| No. of reflections | 1482 | 2678 |
| No. of restraints | 1 | 0 |
| Δρmax, Δρmin (e Å−3) | 0.19, −0.15 | 0.35, −0.29 |
| Absolute structure | Flack x determined using 652 quotients [(I +) − (I −)]/[(I +) + (I −)] (Parsons et al., 2013 ▸); Hooft y = 0.11(6) calculated with OLEX2 (Dolomanov et al., 2009 ▸) | – |
| Absolute structure parameter | 0.09 (7) | – |
7. Analytical data
7.1. 4-(1H-Imidazol-1-yl)benzaldehyde, (I)
1H NMR (Bruker Avance III HD 400 MHz, CDCl3): δ 7.26 (m, 1H, Cimid H), 7.39 (m, 1H, Cimid H), 7.60 (d, 2H, Caryl H, J = 8.6 Hz), 7.99 (s, 1H, Cimid H), 8.03 (d, 2H, Caryl H, J = 8.6 Hz), 10.05 [s, 1H, C(O)H]. 13C NMR (13C{1H}, 100.6 MHz, CDCl3): δ 117.54 (C imidH), 120.97 (C arylH), 131.23 (C imidH), 131.48 (C arylH), 134.84 (C aryl), 135.28 (C imidH), 141.60 (C aryl), 190.48 [C(O)H]. IR (Thermo Nicolet iS50, ATR, cm−1): 3138 (w, Caryl—H str), 3109 (m, Caryl—H str), 2818 and 2746 (m, =C—H aldehyde Fermi doublet str), 1676 (s, C=O str), 1604 (s, arom. C=C str), 1519 (s, arom. C=C str), 1481 (s, arom. C=C str), 1439 (m), 1400 (s), 1375 (s), 1310 (s), 1268 (s), 1220 (s), 1171 (s), 1120 (m), 1105 (m), 1059 (s), 971 (m), 959 (s), 902 (w), 830 (s), 752 (s), 692 (m), 752 (s), 692 (m), 648 (s), 617 (m), 530 (m), 513 (s), 447 (m), 413 (m). GC–MS (Agilent Technologies 7890A GC/5975C MS): M + = 172 amu.
7.2. 1-(4-Methoxyphenyl)-1H-imidazole, (II)
1H NMR (Bruker Avance III HD 400 MHz, CDCl3): δ 3.85 (s, 3H, OCH 3), 6.98 (d, 2H, Caryl H, J = 8.9 Hz), 7.20 (m, 2H, Cimid H), 7.30 (d, 2H, Caryl H, J = 8.9 Hz), 7.78 (m, 1H, Cimid H). 13C NMR (13C{1H}, 100.6 MHz, CDCl3): δ 55.56 (OCH3), 114.87 (C arylH), 118.83 (C imidH), 123.19 (C arylH), 129.97 (C aryl), 130.68 (C imidH), 135.89 (C imidH), 158.92 (C aryl). IR (Thermo Nicolet iS50, ATR, cm−1): 3128 (m, Caryl—H str), 3107 (m, Caryl—H str), 2961 (w, Calkyl—H str), 2918 (w, Calkyl—H str), 2838 (m, Calkyl—H str), 2052 (w), 1877 (w), 1634 (w), 1610 (m), 1591 (w), 1517 (s, arom. C=C str), 1471 (s, arom. C=C str), 1459 (m), 1447 (w), 1332 (m), 1321 (s), 1302 (m), 1267 (s), 1256 (s), 1241 (s), 1192 (s), 1173 (m), 1109 (s), 1100 (s), 1061 (s), 1029 (s), 961 (m), 910 (m), 873 (w), 840 (s), 823 (s), 798 (s), 780 (s), 762 (s), 664 (s), 649 (s), 614 (m), 539 (s), 490 (m), 434 (w). GC–MS (Agilent Technologies 7890A GC/5975C MS): M + = 174 amu.
Supplementary Material
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989023005480/jy2032sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989023005480/jy2032Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989023005480/jy2032IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989023005480/jy2032Isup4.cml
Supporting information file. DOI: 10.1107/S2056989023005480/jy2032IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported by Vassar College. X-ray facilities were provided by the U.S. National Science Foundation.
supplementary crystallographic information
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Crystal data
| C10H8N2O | F(000) = 180 |
| Mr = 172.18 | Dx = 1.422 Mg m−3 |
| Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
| a = 3.7749 (2) Å | Cell parameters from 5426 reflections |
| b = 7.3711 (5) Å | θ = 3.1–71.6° |
| c = 14.4524 (9) Å | µ = 0.77 mm−1 |
| β = 91.096 (2)° | T = 125 K |
| V = 402.07 (4) Å3 | Plate, clear colourless |
| Z = 2 | 0.37 × 0.20 × 0.05 mm |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Data collection
| Bruker APEXII CCD diffractometer | 1482 independent reflections |
| Radiation source: Cu IuS micro-focus source | 1466 reflections with I > 2σ(I) |
| Detector resolution: 8.3333 pixels mm-1 | Rint = 0.029 |
| φ and ω scans | θmax = 71.6°, θmin = 3.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −4→4 |
| Tmin = 0.80, Tmax = 0.96 | k = −8→7 |
| 5673 measured reflections | l = −17→16 |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0471P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
| S = 1.14 | Δρmax = 0.19 e Å−3 |
| 1482 reflections | Δρmin = −0.15 e Å−3 |
| 119 parameters | Extinction correction: SHELXL2017 (Sheldrick, 2015b) |
| 1 restraint | Extinction coefficient: 0.021 (6) |
| Primary atom site location: dual | Absolute structure: Flack x determined using 652 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013); Hooft y = 0.11(6) calculated with OLEX2 (Dolomanov et al., 2009). |
| Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.09 (7) |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.8970 (4) | 0.9617 (2) | 0.09534 (10) | 0.0289 (4) | |
| N1 | 0.3041 (4) | 0.2861 (2) | 0.33233 (10) | 0.0166 (4) | |
| N2 | 0.2148 (4) | 0.1490 (2) | 0.46723 (11) | 0.0222 (4) | |
| C1 | 0.8366 (5) | 0.8021 (3) | 0.07934 (13) | 0.0230 (4) | |
| H1A | 0.889378 | 0.758391 | 0.019326 | 0.028* | |
| C2 | 0.6890 (5) | 0.6719 (3) | 0.14516 (12) | 0.0185 (4) | |
| C3 | 0.6418 (5) | 0.4920 (3) | 0.11753 (13) | 0.0203 (4) | |
| H3A | 0.698927 | 0.4571 | 0.056322 | 0.024* | |
| C4 | 0.5120 (5) | 0.3631 (3) | 0.17851 (12) | 0.0192 (4) | |
| H4A | 0.480518 | 0.240754 | 0.159434 | 0.023* | |
| C5 | 0.4286 (4) | 0.4165 (3) | 0.26824 (12) | 0.0169 (4) | |
| C6 | 0.4704 (4) | 0.5971 (3) | 0.29652 (12) | 0.0183 (4) | |
| H6A | 0.409116 | 0.632564 | 0.357352 | 0.022* | |
| C7 | 0.6015 (5) | 0.7236 (3) | 0.23531 (13) | 0.0199 (4) | |
| H7A | 0.632366 | 0.846022 | 0.254394 | 0.024* | |
| C8 | 0.1451 (4) | 0.1207 (3) | 0.31214 (12) | 0.0191 (4) | |
| H8A | 0.086412 | 0.073743 | 0.25258 | 0.023* | |
| C9 | 0.0906 (5) | 0.0395 (3) | 0.39529 (13) | 0.0212 (4) | |
| H9A | −0.017271 | −0.075833 | 0.403072 | 0.025* | |
| C10 | 0.3399 (5) | 0.2943 (3) | 0.42704 (13) | 0.0204 (4) | |
| H10A | 0.443164 | 0.393702 | 0.45957 | 0.025* |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0395 (9) | 0.0225 (9) | 0.0249 (7) | −0.0053 (6) | 0.0026 (6) | 0.0022 (6) |
| N1 | 0.0195 (7) | 0.0148 (9) | 0.0154 (7) | 0.0001 (6) | −0.0004 (5) | 0.0002 (6) |
| N2 | 0.0268 (8) | 0.0210 (10) | 0.0188 (7) | −0.0002 (6) | 0.0009 (6) | 0.0014 (6) |
| C1 | 0.0245 (9) | 0.0236 (12) | 0.0209 (9) | −0.0008 (8) | −0.0004 (7) | 0.0000 (8) |
| C2 | 0.0179 (8) | 0.0201 (11) | 0.0175 (8) | 0.0005 (7) | −0.0013 (7) | 0.0002 (7) |
| C3 | 0.0212 (9) | 0.0230 (11) | 0.0166 (9) | 0.0020 (7) | 0.0012 (7) | −0.0018 (7) |
| C4 | 0.0230 (9) | 0.0166 (11) | 0.0180 (8) | −0.0005 (7) | −0.0001 (7) | −0.0021 (7) |
| C5 | 0.0151 (8) | 0.0176 (10) | 0.0180 (8) | 0.0009 (7) | −0.0018 (6) | 0.0007 (7) |
| C6 | 0.0212 (8) | 0.0175 (10) | 0.0164 (8) | 0.0015 (7) | 0.0006 (7) | −0.0021 (7) |
| C7 | 0.0213 (9) | 0.0162 (10) | 0.0221 (10) | 0.0002 (7) | −0.0015 (7) | −0.0017 (7) |
| C8 | 0.0202 (8) | 0.0168 (10) | 0.0203 (8) | −0.0005 (7) | −0.0009 (6) | −0.0027 (7) |
| C9 | 0.0219 (9) | 0.0187 (11) | 0.0229 (9) | 0.0004 (7) | 0.0007 (7) | 0.0016 (7) |
| C10 | 0.0243 (9) | 0.0207 (11) | 0.0163 (9) | 0.0005 (7) | −0.0013 (7) | −0.0012 (7) |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Geometric parameters (Å, º)
| O1—C1 | 1.219 (3) | C3—H3A | 0.9500 |
| N1—C10 | 1.374 (2) | C4—C5 | 1.397 (2) |
| N1—C8 | 1.388 (2) | C4—H4A | 0.9500 |
| N1—C5 | 1.421 (2) | C5—C6 | 1.401 (3) |
| N2—C10 | 1.311 (2) | C6—C7 | 1.383 (3) |
| N2—C9 | 1.391 (2) | C6—H6A | 0.9500 |
| C1—C2 | 1.469 (2) | C7—H7A | 0.9500 |
| C1—H1A | 0.9500 | C8—C9 | 1.362 (3) |
| C2—C3 | 1.395 (3) | C8—H8A | 0.9500 |
| C2—C7 | 1.403 (2) | C9—H9A | 0.9500 |
| C3—C4 | 1.391 (3) | C10—H10A | 0.9500 |
| C10—N1—C8 | 106.39 (15) | C4—C5—N1 | 119.84 (17) |
| C10—N1—C5 | 126.28 (15) | C6—C5—N1 | 119.32 (16) |
| C8—N1—C5 | 127.19 (15) | C7—C6—C5 | 119.59 (17) |
| C10—N2—C9 | 105.21 (15) | C7—C6—H6A | 120.2 |
| O1—C1—C2 | 125.41 (17) | C5—C6—H6A | 120.2 |
| O1—C1—H1A | 117.3 | C6—C7—C2 | 120.28 (18) |
| C2—C1—H1A | 117.3 | C6—C7—H7A | 119.9 |
| C3—C2—C7 | 119.54 (17) | C2—C7—H7A | 119.9 |
| C3—C2—C1 | 118.92 (15) | C9—C8—N1 | 105.83 (16) |
| C7—C2—C1 | 121.53 (17) | C9—C8—H8A | 127.1 |
| C4—C3—C2 | 120.81 (16) | N1—C8—H8A | 127.1 |
| C4—C3—H3A | 119.6 | C8—C9—N2 | 110.49 (18) |
| C2—C3—H3A | 119.6 | C8—C9—H9A | 124.8 |
| C3—C4—C5 | 118.95 (17) | N2—C9—H9A | 124.8 |
| C3—C4—H4A | 120.5 | N2—C10—N1 | 112.07 (16) |
| C5—C4—H4A | 120.5 | N2—C10—H10A | 124.0 |
| C4—C5—C6 | 120.84 (16) | N1—C10—H10A | 124.0 |
| O1—C1—C2—C3 | −178.55 (18) | N1—C5—C6—C7 | 178.08 (15) |
| O1—C1—C2—C7 | 0.2 (3) | C5—C6—C7—C2 | 0.6 (2) |
| C7—C2—C3—C4 | −0.6 (3) | C3—C2—C7—C6 | 0.2 (3) |
| C1—C2—C3—C4 | 178.21 (16) | C1—C2—C7—C6 | −178.52 (16) |
| C2—C3—C4—C5 | 0.1 (3) | C10—N1—C8—C9 | 0.62 (19) |
| C3—C4—C5—C6 | 0.7 (3) | C5—N1—C8—C9 | 176.67 (16) |
| C3—C4—C5—N1 | −178.42 (15) | N1—C8—C9—N2 | −0.6 (2) |
| C10—N1—C5—C4 | 153.02 (17) | C10—N2—C9—C8 | 0.4 (2) |
| C8—N1—C5—C4 | −22.3 (2) | C9—N2—C10—N1 | 0.0 (2) |
| C10—N1—C5—C6 | −26.2 (3) | C8—N1—C10—N2 | −0.4 (2) |
| C8—N1—C5—C6 | 158.54 (16) | C5—N1—C10—N2 | −176.52 (16) |
| C4—C5—C6—C7 | −1.1 (2) |
4-(1H-Imidazol-1-yl)benzaldehyde (I) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C8—H8A···O1i | 0.95 | 2.51 | 3.458 (2) | 176 |
| C10—H10A···N2ii | 0.95 | 2.51 | 3.449 (2) | 173 |
Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, y+1/2, −z+1.
1-(4-Methoxyphenyl)-1H-imidazole (II) . Crystal data
| C10H10N2O | F(000) = 368 |
| Mr = 174.20 | Dx = 1.318 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.5663 (12) Å | Cell parameters from 8588 reflections |
| b = 11.2143 (16) Å | θ = 2.4–30.4° |
| c = 9.1635 (13) Å | µ = 0.09 mm−1 |
| β = 94.448 (2)° | T = 125 K |
| V = 877.6 (2) Å3 | Plate, colourless |
| Z = 4 | 0.40 × 0.25 × 0.15 mm |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Data collection
| Bruker APEXII CCD diffractometer | 2678 independent reflections |
| Radiation source: sealed X-ray tube, Bruker APEXII CCD | 2332 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.031 |
| Detector resolution: 8.3333 pixels mm-1 | θmax = 30.6°, θmin = 2.4° |
| φ and ω scans | h = −12→12 |
| Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −16→15 |
| Tmin = 0.92, Tmax = 0.99 | l = −13→13 |
| 21397 measured reflections |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.119 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0687P)2 + 0.1966P] where P = (Fo2 + 2Fc2)/3 |
| 2678 reflections | (Δ/σ)max < 0.001 |
| 119 parameters | Δρmax = 0.35 e Å−3 |
| 0 restraints | Δρmin = −0.29 e Å−3 |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.50111 (8) | 0.64826 (6) | 0.27442 (7) | 0.01696 (16) | |
| N2 | 0.35189 (9) | 0.60120 (7) | 0.07295 (8) | 0.02110 (17) | |
| O1 | 0.98420 (8) | 0.63969 (6) | 0.71768 (7) | 0.02769 (18) | |
| C1 | 1.02429 (11) | 0.53203 (10) | 0.79493 (10) | 0.0289 (2) | |
| H1A | 1.108753 | 0.547969 | 0.87077 | 0.043* | |
| H1B | 1.059244 | 0.472373 | 0.726426 | 0.043* | |
| H1C | 0.932403 | 0.501862 | 0.840608 | 0.043* | |
| C2 | 0.86571 (10) | 0.63397 (8) | 0.60922 (9) | 0.02084 (18) | |
| C3 | 0.81994 (11) | 0.74301 (8) | 0.54587 (10) | 0.02479 (19) | |
| H3A | 0.870761 | 0.814315 | 0.579384 | 0.03* | |
| C4 | 0.70105 (11) | 0.74809 (8) | 0.43457 (9) | 0.02198 (18) | |
| H4A | 0.670793 | 0.822403 | 0.391376 | 0.026* | |
| C5 | 0.62626 (10) | 0.64337 (7) | 0.38651 (9) | 0.01708 (17) | |
| C6 | 0.67205 (10) | 0.53468 (7) | 0.44827 (9) | 0.01901 (17) | |
| H6A | 0.621215 | 0.463503 | 0.414318 | 0.023* | |
| C7 | 0.79220 (10) | 0.52919 (8) | 0.55986 (9) | 0.02071 (18) | |
| H7A | 0.823565 | 0.454653 | 0.601777 | 0.025* | |
| C8 | 0.37965 (10) | 0.72974 (7) | 0.26290 (9) | 0.01978 (18) | |
| H8A | 0.362414 | 0.793692 | 0.327719 | 0.024* | |
| C9 | 0.28976 (10) | 0.69928 (8) | 0.13921 (9) | 0.02107 (18) | |
| H9A | 0.197198 | 0.739844 | 0.10349 | 0.025* | |
| C10 | 0.47846 (10) | 0.57358 (7) | 0.15758 (9) | 0.01911 (18) | |
| H10A | 0.545959 | 0.509019 | 0.139087 | 0.023* |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0198 (3) | 0.0156 (3) | 0.0153 (3) | 0.0015 (2) | 0.0003 (2) | −0.0014 (2) |
| N2 | 0.0226 (4) | 0.0219 (4) | 0.0183 (3) | 0.0020 (3) | −0.0011 (3) | −0.0016 (3) |
| O1 | 0.0249 (3) | 0.0327 (4) | 0.0239 (3) | −0.0069 (3) | −0.0077 (3) | 0.0039 (3) |
| C1 | 0.0249 (4) | 0.0389 (5) | 0.0222 (4) | −0.0024 (4) | −0.0028 (3) | 0.0082 (4) |
| C2 | 0.0194 (4) | 0.0251 (4) | 0.0178 (4) | −0.0035 (3) | 0.0003 (3) | 0.0010 (3) |
| C3 | 0.0271 (4) | 0.0204 (4) | 0.0260 (4) | −0.0055 (3) | −0.0037 (3) | −0.0010 (3) |
| C4 | 0.0264 (4) | 0.0162 (4) | 0.0228 (4) | −0.0015 (3) | −0.0013 (3) | 0.0004 (3) |
| C5 | 0.0188 (4) | 0.0176 (4) | 0.0148 (3) | −0.0004 (3) | 0.0009 (3) | −0.0006 (3) |
| C6 | 0.0205 (4) | 0.0167 (4) | 0.0195 (4) | −0.0014 (3) | −0.0001 (3) | −0.0001 (3) |
| C7 | 0.0214 (4) | 0.0205 (4) | 0.0200 (4) | −0.0013 (3) | −0.0001 (3) | 0.0031 (3) |
| C8 | 0.0231 (4) | 0.0166 (4) | 0.0197 (4) | 0.0034 (3) | 0.0024 (3) | −0.0010 (3) |
| C9 | 0.0211 (4) | 0.0209 (4) | 0.0211 (4) | 0.0037 (3) | 0.0005 (3) | 0.0011 (3) |
| C10 | 0.0221 (4) | 0.0181 (4) | 0.0170 (3) | 0.0018 (3) | 0.0004 (3) | −0.0031 (3) |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Geometric parameters (Å, º)
| N1—C10 | 1.3612 (10) | C3—C4 | 1.3854 (12) |
| N1—C8 | 1.3827 (10) | C3—H3A | 0.9500 |
| N1—C5 | 1.4271 (10) | C4—C5 | 1.3928 (11) |
| N2—C10 | 1.3200 (10) | C4—H4A | 0.9500 |
| N2—C9 | 1.3828 (11) | C5—C6 | 1.3876 (11) |
| O1—C2 | 1.3658 (10) | C6—C7 | 1.3947 (11) |
| O1—C1 | 1.4279 (12) | C6—H6A | 0.9500 |
| C1—H1A | 0.9800 | C7—H7A | 0.9500 |
| C1—H1B | 0.9800 | C8—C9 | 1.3634 (11) |
| C1—H1C | 0.9800 | C8—H8A | 0.9500 |
| C2—C7 | 1.3920 (12) | C9—H9A | 0.9500 |
| C2—C3 | 1.3967 (12) | C10—H10A | 0.9500 |
| C10—N1—C8 | 106.62 (7) | C5—C4—H4A | 120.3 |
| C10—N1—C5 | 126.57 (7) | C6—C5—C4 | 120.21 (8) |
| C8—N1—C5 | 126.81 (7) | C6—C5—N1 | 120.01 (7) |
| C10—N2—C9 | 104.78 (7) | C4—C5—N1 | 119.78 (7) |
| C2—O1—C1 | 117.23 (7) | C5—C6—C7 | 120.46 (7) |
| O1—C1—H1A | 109.5 | C5—C6—H6A | 119.8 |
| O1—C1—H1B | 109.5 | C7—C6—H6A | 119.8 |
| H1A—C1—H1B | 109.5 | C2—C7—C6 | 119.38 (8) |
| O1—C1—H1C | 109.5 | C2—C7—H7A | 120.3 |
| H1A—C1—H1C | 109.5 | C6—C7—H7A | 120.3 |
| H1B—C1—H1C | 109.5 | C9—C8—N1 | 105.73 (7) |
| O1—C2—C7 | 124.61 (8) | C9—C8—H8A | 127.1 |
| O1—C2—C3 | 115.48 (8) | N1—C8—H8A | 127.1 |
| C7—C2—C3 | 119.91 (8) | C8—C9—N2 | 110.64 (7) |
| C4—C3—C2 | 120.57 (8) | C8—C9—H9A | 124.7 |
| C4—C3—H3A | 119.7 | N2—C9—H9A | 124.7 |
| C2—C3—H3A | 119.7 | N2—C10—N1 | 112.23 (7) |
| C3—C4—C5 | 119.47 (8) | N2—C10—H10A | 123.9 |
| C3—C4—H4A | 120.3 | N1—C10—H10A | 123.9 |
| C1—O1—C2—C7 | −6.43 (13) | N1—C5—C6—C7 | −178.75 (7) |
| C1—O1—C2—C3 | 174.10 (8) | O1—C2—C7—C6 | 179.88 (8) |
| O1—C2—C3—C4 | 179.87 (8) | C3—C2—C7—C6 | −0.68 (13) |
| C7—C2—C3—C4 | 0.38 (14) | C5—C6—C7—C2 | 0.19 (13) |
| C2—C3—C4—C5 | 0.41 (14) | C10—N1—C8—C9 | 0.16 (9) |
| C3—C4—C5—C6 | −0.91 (13) | C5—N1—C8—C9 | 179.98 (7) |
| C3—C4—C5—N1 | 178.46 (7) | N1—C8—C9—N2 | −0.15 (10) |
| C10—N1—C5—C6 | −44.15 (12) | C10—N2—C9—C8 | 0.07 (10) |
| C8—N1—C5—C6 | 136.07 (9) | C9—N2—C10—N1 | 0.03 (10) |
| C10—N1—C5—C4 | 136.49 (9) | C8—N1—C10—N2 | −0.12 (10) |
| C8—N1—C5—C4 | −43.30 (12) | C5—N1—C10—N2 | −179.94 (7) |
| C4—C5—C6—C7 | 0.61 (13) |
1-(4-Methoxyphenyl)-1H-imidazole (II) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C8—H8A···N2i | 0.95 | 2.55 | 3.4391 (11) | 157 |
| C9—H9A···O1ii | 0.95 | 2.56 | 3.3048 (11) | 136 |
| C10—H10A···N2iii | 0.95 | 2.52 | 3.3004 (11) | 140 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x−1, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z.
Funding Statement
Funding for this research was provided by: National Science Foundation (grant Nos. 0521237 and 0911324 to J. M. Tanski).
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989023005480/jy2032sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989023005480/jy2032Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989023005480/jy2032IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989023005480/jy2032Isup4.cml
Supporting information file. DOI: 10.1107/S2056989023005480/jy2032IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report