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

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)].

Full text

678 https://doi.org/10.1107/S2056989023005480 Acta Cryst. (2023). E79, 678–681
research communications
Received 8 June 2023
Accepted 21 June 2023
Edited by J. Reibenspies, Texas A & M Univer-
sity, USA
Keywords: crystal structure; 1-phenyl-1H-
imidazole derivatives; weak intermolecular
interactions; non-centrosymmetric space group.
CCDC references:2267421; 2267419
Supporting information:this article has
supporting information at journals.iucr.org/e
Crystallographic and spectroscopic characteriza-
tion of two 1-phenyl-1H-imidazoles: 4-(1H-
imidazol-1-yl)benzaldehyde and 1-(4-methoxy-
phenyl)-1H-imidazole
Isobelle F. McClements, Clara R. Wiesler and Joseph M. Tanski*
Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA. *Correspondence e-mail: jotanski@vassar.edu
The title compounds, C
10
H
8
N
2
O, (I), and C
10
H
10
N
2
O, (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-inflamma-
tory 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 (Schro
¨der 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
(Milenkovic
´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
ISSN 2056-9890
Published under a CC BY 4.0 licence

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).
3. Supramolecular features
The molecules of benzaldehyde derivative (I) are held toge-
ther 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O1
i
) and
imidazole N atoms (C10—H10AN2
ii
). 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) A
˚, a plane-to-centroid distance of
3.5002 (10) A
˚, and a ring shift of 1.414 (3) A
˚. Fig. 3 displays a
di-periodic sheet with a thickness roughly equivalent to the
length of the caxis, 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 P2
1
and is therefore a polar material in the
solid state. Polar organic materials formed by achiral mol-
ecules are of interest in crystal engineering, in particular for
nonlinear optical materials (Merritt & Tanski, 2018).
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O1
ii
) and an imidazole N atom (C10—H10AN2
iii
).
A third weak interaction links the remaining imidazole H
atom with the imidazole N atom (C8—H8AN2
i
). Unlike
benzaldehyde derivative (I), anisole derivative (II) does not
exhibit any -stacking geometrical arrangement of the arene
rings and the molecules pack centrosymmetrically (Fig. 5).
4. Database survey
The Cambridge Structural Database (CSD; Groom et al.,
2016) contains six simple para-X-substituted 1-phenyl-1H-
research communications
Acta Cryst. (2023). E79, 678–681 McClements et al. C
10
H
8
N
2
O and C
10
H
10
N
2
O679
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.
Table 1
Hydrogen-bond geometry (A
˚,) for (I).
D—HAD—H HADAD—HA
C8—H8AO1
i
0.95 2.51 3.458 (2) 176
C10—H10AN2
ii
0.95 2.51 3.449 (2) 173
Symmetry codes: (i) x1;y1;z; (ii) xþ1;yþ1
2;zþ1.
Table 2
Hydrogen-bond geometry (A
˚,) for (II).
D—HAD—H HADAD—HA
C8—H8AN2
i
0.95 2.55 3.4391 (11) 157
C9—H9AO1
ii
0.95 2.56 3.3048 (11) 136
C10—H10AN2
iii
0.95 2.52 3.3004 (11) 140
Symmetry codes: (i) x;yþ3
2;zþ1
2; (ii) x1;yþ3
2;z1
2; (iii) xþ1;yþ1;z.
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 4
A view of the intermolecular interactions in 1-(4-methoxyphenyl)-1H-
imidazole, (II). [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.]
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
2,z+1.]

imidazole derivatives: X= –NH
2
(CSD refcode MUFCAS;
Liang et al., 2009), –Br (PAJDUD; Ding et al., 2021), –I
(FIQFUJ; Bejan et al., 2018), –CO
2
H (IKAWAT; Zheng et al.,
2011), –CO
2
CH
3
(BEMVUN; Khattri et al., 2016) and
–COCH
3
(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 deriva-
tives 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.
680 McClements et al. C
10
H
8
N
2
O and C
10
H
10
N
2
OActa Cryst. (2023). E79, 678–681
research communications
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 C
10
H
8
N
2
OC
10
H
10
N
2
O
M
r
172.18 174.20
Crystal system, space group Monoclinic, P2
1
Monoclinic, P2
1
/c
a,b,c(A
˚) 3.7749 (2), 7.3711 (5), 14.4524 (9) 8.5663 (12), 11.2143 (16), 9.1635 (13)
() 91.096 (2) 94.448 (2)
V(A
˚
3
) 402.07 (4) 877.6 (2)
Z24
Radiation type Cu KMo K
(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>2(I)] reflections
5673, 1482, 1466 21397, 2678, 2332
R
int
0.029 0.031
(sin /)
max
(A
˚
1
) 0.615 0.715
Refinement
R[F
2
>2(F
2
)], wR(F
2
), S0.027, 0.079, 1.14 0.040, 0.119, 1.04
No. of reflections 1482 2678
No. of restraints 1 0

max
,
min
(e A
˚
3
) 0.19, 0.15 0.35, 0.29
Absolute structure Flack xdetermined 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).
Figure 5
A view of the molecular packing in 1-(4-methoxyphenyl)-1H-imidazole,
(II).

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 A
˚and U
iso
(H) = 1.2U
eq
(C) for aryl H atoms, and
C—H = 0.98 A
˚and U
iso
(H) = 1.5U
eq
(C) for methyl H atoms.
7. Analytical data
7.1. 4-(1H-Imidazol-1-yl)benzaldehyde, (I)
1
H NMR (Bruker Avance III HD 400 MHz, CDCl
3
): 7.26
(m, 1H, C
imid
H), 7.39 (m, 1H, C
imid
H), 7.60 (d,2H,C
aryl
H,J=
8.6 Hz), 7.99 (s, 1H, C
imid
H), 8.03 (d, 2H, C
aryl
H,J= 8.6 Hz),
10.05 [s, 1H, C(O)H].
13
CNMR(
13
C{
1
H}, 100.6 MHz, CDCl
3
):
117.54 (C
imid
H), 120.97 (C
aryl
H), 131.23 (C
imid
H), 131.48
(C
aryl
H), 134.84 (C
aryl
), 135.28 (C
imid
H), 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.
CC 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 Tech-
nologies 7890A GC/5975C MS): M
+
= 172 amu.
7.2. 1-(4-Methoxyphenyl)-1H-imidazole, (II)
1
H NMR (Bruker Avance III HD 400 MHz, CDCl
3
): 3.85
(s, 3H, OCH
3
), 6.98 (d, 2H, C
aryl
H,J= 8.9 Hz), 7.20 (m, 2H,
C
imid
H), 7.30 (d,2H,C
aryl
H,J= 8.9 Hz), 7.78 (m,1H,C
imid
H).
13
CNMR(
13
C{
1
H}, 100.6 MHz, CDCl
3
): 55.56 (OCH
3
),
114.87 (C
aryl
H), 118.83 (C
imid
H), 123.19 (C
aryl
H), 129.97
(C
aryl
), 130.68 (C
imid
H), 135.89 (C
imid
H), 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.
CC 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.
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.
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.
Bruker (2013). SAINT and APEX3. Bruxer AXS Inc., Madison,
Wisconsin, USA.
Bruker (2016). SADABS. Bruxer AXS Inc., Madison, Wisconsin,
USA.
Ding, B., Ma, L., Huang, Z., Ma, X. & Tian, H. (2021). Sci. Adv. 7,
eabf9668.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. &
Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
Emel’yanenko, V. N., Kaliner, M., Strassner, T. & Verevkin, S. P.
(2017). Fluid Phase Equilib. 433, 40–49.
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta
Cryst. B72, 171–179.
Hussain, T., Siddiqui, H. L., Zia-ur-Rehman, M., Masoom Yasinzai,
M. & Parvez, M. (2009). Eur. J. Med. Chem. 44, 4654–4660.
Ibrahim, H., Bala, M. D. & Omondi, B. (2012). Acta Cryst. E68, o2305.
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.
Liang, L., Li, Z. & Zhou, X. (2009). Org. Lett. 11, 3294–3297.
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.
Merritt, H. & Tanski, J. M. (2018). J. Chem. Crystallogr. 48, 109–116.
Milenkovic
´, M. R., Papastavrou, A. T., Radanovic
´, D., Pevec, A.,
Jaglic
ˇic
´, Z., Zlatar, M., Gruden, M., Vougioukalakis, G. C., Turel, I.,
And
-elkovic
´,K.&C
ˇobeljic
´, B. (2019). Polyhedron,165, 22–30.
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–
259.
Schro
¨der, K., Enthaler, S., Bitterlich, B., Schulz, T., Spannenberg, A.,
Tse, M. K., Junge, K. & Beller, M. (2009). Chem. Eur. J. 15, 5471–
5481.
Shalini, K., Sharma, P. K. & Kumar, N. (2010). Der Chem. Sinica,1,6–
47.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Xi, Z., Liu, F., Zhou, Y. & Chen, W. (2008). Tetrahedron,64, 4254–
4259.
Zheng, Z., Geng, W.-Q., Wu, Z.-C. & Zhou, H.-P. (2011). Acta Cryst.
E67, o524.
research communications
Acta Cryst. (2023). E79, 678–681 McClements et al. C
10
H
8
N
2
O and C
10
H
10
N
2
O681

supporting information
sup-1
Acta Cryst. (2023). E79, 678-681
supporting information
Acta Cryst. (2023). E79, 678-681 [https://doi.org/10.1107/S2056989023005480]
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, Clara R. Wiesler and Joseph M. Tanski
Computing details
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)
Crystal data
C10H8N2O
Mr = 172.18
Monoclinic, P21
a = 3.7749 (2) Å
b = 7.3711 (5) Å
c = 14.4524 (9) Å
β = 91.096 (2)°
V = 402.07 (4) Å3
Z = 2
F(000) = 180
Dx = 1.422 Mg m−3
Cu Kα radiation, λ = 1.54178 Å
Cell parameters from 5426 reflections
θ = 3.1–71.6°
µ = 0.77 mm−1
T = 125 K
Plate, clear colourless
0.37 × 0.20 × 0.05 mm
Data collection
Bruker APEXII CCD
diffractometer
Radiation source: Cu IuS micro-focus source
Detector resolution: 8.3333 pixels mm-1
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
Tmin = 0.80, Tmax = 0.96
5673 measured reflections
1482 independent reflections
1466 reflections with I > 2σ(I)
Rint = 0.029
θmax = 71.6°, θmin = 3.1°
h = −4→4
k = −8→7
l = −17→16
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.027
wR(F2) = 0.079
S = 1.14
1482 reflections
119 parameters
1 restraint
Primary atom site location: dual
Secondary atom site location: difference Fourier
map

supporting information
sup-2
Acta Cryst. (2023). E79, 678-681
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0471P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.19 e Å−3
Δρmin = −0.15 e Å−3
Extinction correction: SHELXL2017
(Sheldrick, 2015b)
Extinction coefficient: 0.021 (6)
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)
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyz U
iso*/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*
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)

supporting information
sup-3
Acta Cryst. (2023). E79, 678-681
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)
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)

supporting information
sup-4
Acta Cryst. (2023). E79, 678-681
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)
D—H···AD—H H···AD···AD—H···A
C8—H8A···O1i0.95 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
Mr = 174.20
Monoclinic, P21/c
a = 8.5663 (12) Å
b = 11.2143 (16) Å
c = 9.1635 (13) Å
β = 94.448 (2)°
V = 877.6 (2) Å3
Z = 4
F(000) = 368
Dx = 1.318 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 8588 reflections
θ = 2.4–30.4°
µ = 0.09 mm−1
T = 125 K
Plate, colourless
0.40 × 0.25 × 0.15 mm
Data collection
Bruker APEXII CCD
diffractometer
Radiation source: sealed X-ray tube, Bruker
APEXII CCD
Graphite monochromator
Detector resolution: 8.3333 pixels mm-1
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
Tmin = 0.92, Tmax = 0.99
21397 measured reflections
2678 independent reflections
2332 reflections with I > 2σ(I)
Rint = 0.031
θmax = 30.6°, θmin = 2.4°
h = −12→12
k = −16→15
l = −13→13
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.040
wR(F2) = 0.119
S = 1.04
2678 reflections
119 parameters
0 restraints
Primary atom site location: dual
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0687P)2 + 0.1966P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.35 e Å−3
Δρmin = −0.29 e Å−3
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.

supporting information
sup-5
Acta Cryst. (2023). E79, 678-681
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzU
iso*/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*
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)
Geometric parameters (Å, º)
N1—C10 1.3612 (10) C3—C4 1.3854 (12)
N1—C8 1.3827 (10) C3—H3A 0.9500

supporting information
sup-6
Acta Cryst. (2023). E79, 678-681
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)
D—H···AD—H H···AD···AD—H···A
C8—H8A···N2i0.95 2.55 3.4391 (11) 157

supporting information
sup-7
Acta Cryst. (2023). E79, 678-681
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.