Crystallographic and spectroscopic characterization of two 1-phenyl-1H-imidazoles: 4-(1H-imidazol-1-yl)benzaldehyde and 1-(4-meth­oxy­phen­yl)-1H-imidazole

McClements, I.F.; Wiesler, C.R.; Tanski, J.M.

doi:10.1107/S2056989023005480

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 7| July 2023| Pages 678-681

https://doi.org/10.1107/S2056989023005480

Open

access

Crystallographic and spectroscopic characterization of two 1-phenyl-1H-imidazoles: 4-(1H-imidazol-1-yl)benzaldehyde and 1-(4-methoxyphenyl)-1H-imidazole

Isobelle F. McClements,^a Clara R. Wiesler ^a and Joseph M. Tanski ^a ^*

^aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
^*Correspondence e-mail: jotanski@vassar.edu

Edited by J. Reibenspies, Texas A & M University, USA (Received 8 June 2023; accepted 21 June 2023; online 30 June 2023)

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)].

Keywords: crystal structure; 1-phenyl-1H-imidazole derivatives; weak intermolecular interactions; non-centrosymmetric space group.

CCDC references: 2267421; 2267419

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 ).

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) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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 + $[{1\over 2}]$ , −z + 1.]

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).

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) .

Figure 4
A view of the intermolecular interactions in 1-(4-methoxyphenyl)-1H-imidazole, (II)

. [Symmetry codes: (i) x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ; (ii) x − 1, −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ ; (iii) −x + 1, −y + 1, −z.]

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[F² > 2σ(F²)], wR(F²), S	0.027, 0.079, 1.14	0.040, 0.119, 1.04
No. of reflections	1482	2678
No. of restraints	1	0
Δρ_max, Δρ_min (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)	–
Computer programs: APEX3 and SAINT (Bruker, 2013 ), SHELXT2018 (Sheldrick, 2015a ), SHELXL2017 (Sheldrick, 2015b ), SHELXTL2014 (Sheldrick, 2008 ), OLEX2 (Dolomanov et al., 2009), and Mercury (Macrae et al., 2020 ).

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, C_imidH), 7.39 (m, 1H, C_imidH), 7.60 (d, 2H, C_arylH, J = 8.6 Hz), 7.99 (s, 1H, C_imidH), 8.03 (d, 2H, C_arylH, 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, C_aryl—H str), 3109 (m, C_aryl—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, OCH₃), 6.98 (d, 2H, C_arylH, J = 8.9 Hz), 7.20 (m, 2H, C_imidH), 7.30 (d, 2H, C_arylH, J = 8.9 Hz), 7.78 (m, 1H, C_imidH). 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, C_aryl—H str), 3107 (m, C_aryl—H str), 2961 (w, C_alkyl—H str), 2918 (w, C_alkyl—H str), 2838 (m, C_alkyl—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.

Supporting information

CCDC references: 2267421; 2267419

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989023005480/jy2032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023005480/jy2032Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023005480/jy2032IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023005480/jy2032Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989023005480/jy2032IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX3 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: SHELXTL2014 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), and Mercury (Macrae et al., 2020).

4-(1H-Imidazol-1-yl)benzaldehyde (I) top

Crystal data top

C₁₀H₈N₂O	F(000) = 180
M_r = 172.18	D_x = 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

Data collection top

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	R_int = 0.029
φ and ω scans	θ_max = 71.6°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −4→4
T_min = 0.80, T_max = 0.96	k = −8→7
5673 measured reflections	l = −17→16

Refinement top

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(F_o²) + (0.0495P)² + 0.0471P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.079	(Δ/σ)_max < 0.001
S = 1.14	Δρ_max = 0.19 e Å⁻³
1482 reflections	Δρ_min = −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)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) top

Crystal data top

C₁₀H₁₀N₂O	F(000) = 368
M_r = 174.20	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2678 independent reflections
Radiation source: sealed X-ray tube, Bruker APEXII CCD	2332 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.3333 pixels mm^-1	θ_max = 30.6°, θ_min = 2.4°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −16→15
T_min = 0.92, T_max = 0.99	l = −13→13
21397 measured reflections

Refinement top

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(F_o²) + (0.0687P)² + 0.1966P] where P = (F_o² + 2F_c²)/3
2678 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the U.S. National Science Foundation.

Funding information

Funding for this research was provided by: National Science Foundation (grant Nos. 0521237 and 0911324 to J. M. Tanski).

References

Ananthu, S., Aneeja, T. & Anilkumar, G. (2021). ChemistrySelect, 6, 9794–9805. CrossRef CAS Google Scholar
Bejan, D., Bahrin, L. G., Shova, S., Sardaru, M., Clima, L., Nicolescu, A., Marangoci, N., Lozan, V. & Janiak, C. (2018). Inorg. Chim. Acta, 482, 275–283. CrossRef CAS Google Scholar
Bruker (2013). SAINT and APEX3. Bruxer AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2016). SADABS. Bruxer AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, B., Ma, L., Huang, Z., Ma, X. & Tian, H. (2021). Sci. Adv. 7, eabf9668. CrossRef PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Emel'yanenko, V. N., Kaliner, M., Strassner, T. & Verevkin, S. P. (2017). Fluid Phase Equilib. 433, 40–49. CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hussain, T., Siddiqui, H. L., Zia-ur-Rehman, M., Masoom Yasinzai, M. & Parvez, M. (2009). Eur. J. Med. Chem. 44, 4654–4660. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ibrahim, H., Bala, M. D. & Omondi, B. (2012). Acta Cryst. E68, o2305. CSD CrossRef IUCr Journals Google Scholar
Khattri, R. B., Morris, D. L., Davis, C. M., Bilinovich, S. M., Caras, A. J., Panzner, M. J., Debord, M. A. & Leeper, T. C. (2016). Molecules, pp. 21. Google Scholar
Liang, L., Li, Z. & Zhou, X. (2009). Org. Lett. 11, 3294–3297. CrossRef PubMed CAS Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Merritt, H. & Tanski, J. M. (2018). J. Chem. Crystallogr. 48, 109–116. CrossRef CAS Google Scholar
Milenković, M. R., Papastavrou, A. T., Radanović, D., Pevec, A., Jagličić, Z., Zlatar, M., Gruden, M., Vougioukalakis, G. C., Turel, I., Anđelković, K. & Čobeljić, B. (2019). Polyhedron, 165, 22–30. Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Schröder, K., Enthaler, S., Bitterlich, B., Schulz, T., Spannenberg, A., Tse, M. K., Junge, K. & Beller, M. (2009). Chem. Eur. J. 15, 5471–5481. Web of Science PubMed Google Scholar
Shalini, K., Sharma, P. K. & Kumar, N. (2010). Der Chem. Sinica, 1, 6–47. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Xi, Z., Liu, F., Zhou, Y. & Chen, W. (2008). Tetrahedron, 64, 4254–4259. CrossRef CAS Google Scholar
Zheng, Z., Geng, W.-Q., Wu, Z.-C. & Zhou, H.-P. (2011). Acta Cryst. E67, o524. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 7| July 2023| Pages 678-681

https://doi.org/10.1107/S2056989023005480

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystallographic and spectroscopic characterization of two 1-phenyl-1H-imidazoles: 4-(1H-imidazol-1-yl)benzaldehyde and 1-(4-meth­­oxy­phen­yl)-1H-imidazole

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

7. Analytical data

7.1. 4-(1H-Imidazol-1-yl)benzaldehyde, (I)

7.2. 1-(4-Meth­oxy­phen­yl)-1H-imidazole, (II)

Supporting information

Acknowledgements

Funding information

References

research communications

Crystallographic and spectroscopic characterization of two 1-phenyl-1H-imidazoles: 4-(1H-imidazol-1-yl)benzaldehyde and 1-(4-methoxyphenyl)-1H-imidazole

3. Supramolecular features

7.2. 1-(4-Methoxyphenyl)-1H-imidazole, (II)