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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 7| Part 9| September 2022| x220924
https://doi.org/10.1107/S2414314622009245

3-Methyl-5-(4-methyl­phen­­oxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

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Sreeramapura D. Archana,a Holalagudu A. Nagma Banu,b Balakrishna Kalluraya,b Hemmige S. Yathirajan,a* Rishik Baleraoc and Ray J. Butcherd

aDepartment of Studies in Chemistry University of Mysore, Manasagangotri, Mysore-570 006, India, bDepartment of Studies in Chemistry Mangalore University Mangalagangotri, Mangalore-574 199, India, cThomas Jefferson High School for Science and Technology, 6560 Braddock Rd Alexandria VA 22312, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
*Correspondence e-mail: yathirajan@hotmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 12 September 2022; accepted 18 September 2022; online 27 September 2022)

In the title compound, C18H16N2O2, the phenyl and pyrazole rings subtend a dihedral angle of 22.68 (8)°. The packing of the title compound features aromatic π–π stacking and weak C—H⋯π inter­actions.

CCDC reference: 2207948

Similar articles
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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Pyrazoles possess many pharmacological activities such as the inhibition of protein glycation, anti­bacterial, anti­fungal, anti­cancer, anti­depressant, anti-inflammatory, anti-tuberculosis and anti­oxidant activity as well as being used as anti­viral agents (Fustero et al., 2011[Fustero, S., Sánchez-Roselló, M., Barrio, P. & Simón-Fuentes, A. (2011). Chem. Rev. 111, 6984-7034.]; Steinbach et al., 2000[Steinbach, G., Lynch, P. M., Phillips, R. K. S., Wallace, M. H., Hawk, E., Gordon, G. B., Wakabayashi, N., Saunders, B., Shen, Y., Fujimura, T., Su, L.-K., Levin, B., Godio, L., Patterson, S., Rodriguez-Bigas, M. A., Jester, S. L., King, K. L., Schumacher, M., Abbruzzese, J., DuBois, R. N., Hittelman, W. N., Zimmerman, S., Sherman, J. W. & Kelloff, G. (2000). N. Engl. J. Med. 342, 1946-1952.]; García-Lozano et al., 1997[García-Lozano, J., Server-Carrió, J., Escrivà, E., Folgado, J.-V., Molla, C. & Lezama, L. (1997). Polyhedron, 16, 939-944.]). The crystal structures of (E)-1,3-dimethyl-5-p-tol­yloxy-1H-pyrazole-4-carbaldehyde o-(6-chloro­pyridazin-3-yl)oxime (Hu et al., 2006[Hu, F.-Z., Chang, Y.-Q., Zhu, Y.-Q., Zou, X.-M. & Yang, H.-Z. (2006). Acta Cryst. E62, o3676-o3677.]), 1-(5-bromo­pyrimidin-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde (Thiruvalluvar et al., 2007[Thiruvalluvar, A., Subramanyam, M., Kalluraya, B. & Lingappa, B. (2007). Acta Cryst. E63, o3362.]), 5-(2,4-di­chloro­phen­oxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (Kumar et al., 2016[Kumar, S. M., Manju, N., Asma, Kalluraya, B., Byrappa, K. & Warad, I. (2016). IUCrData, 1, x161111.]), four 1-aryl-1H-pyrazole-3,4-di­carbox­ylate derivatives (Asma et al., 2018[Asma, Kalluraya, B., Yathirajan, H. S., Rathore, R. S. & Glidewell, C. (2018). Acta Cryst. E74, 1783-1789.]), functionalized 3-(5-ar­yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen­yl)prop-2-en-1-ones (Kiran Kumar et al., 2020[Kiran Kumar, H., Yathirajan, H. S., Harish Chinthal, C., Foro, S. & Glidewell, C. (2020). Acta Cryst. E76, 488-495.]) and two isostructural 3-(5-ar­yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thio­phen-2-yl)prop-2-en-1-ones (Shaibah et al., 2020[Shaibah, M. A. E., Yathirajan, H. S., Manju, N., Kalluraya, B., Rathore, R. S. & Glidewell, C. (2020). Acta Cryst. E76, 48-52.]) have been reported.

As part our studies in this area, we now report the synthesis and crystal structure of the title compound, C18H16N2O2, (1, Fig. 1[link]) . Compound 1 crystallizes in the monoclinic space group P21/c with one mol­ecule in the asymmetric unit. It consists of a C1/C3/C5/N1/N2 pyrazole ring linked to a C13–C18 phenyl ring by a carbon–nitro­gen single bond [C13—N1 = 1.4285 (17) Å]. As a result of the single bond, the pyrazol and phenyl rings are twisted with a dihedral angle of 22.68 (8)°, perhaps due to the steric inter­action between H18 and O2 and between H14 and N2. In the pyrazole ring, the aldehyde group (C3/C4/O1) is slightly twisted with a dihedral angle of 6.43 (10)° as a result of the steric inter­action of this group with the C2 methyl substituent. The C6–C12 toluyl substituent makes dihedral angles of 79.44 (5) and 82.40 (5)° with the pyrazol and phenyl rings, respectively. A short intra­molecular C18—H18⋯O2 contact closes an S(6) ring.

[Figure 1]
Figure 1
Diagram of 1 showing displacement ellipsoids at the 30% probability level. The C18—H18⋯O2 intra­molecular contact is shown by a dashed line.

In the packing, a very weak C11—H11⋯O1 hydrogen bond generates [010] chains (Fig. 2[link], Table 1[link]). In addition, aromatic π–π stacking involving the pyrazole rings in adjacent mol­ecules [centroid-to-centroid distance = 3.8908 (9) Å, slippage = 1.233 Å, symmetry operation 1 − x, 1 − y, 1 − z] is observed. There is also a weak C—H⋯π inter­action involving the toluene rings in adjacent mol­ecules [distance between ring centroid and carbon atom = 3.8075 (17) Å, C—H⋯Cg = 148°, symmetry operation 1 − x, [{1\over 2}] + y, [{1\over 2}] − z].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C18—H18⋯O2 0.95 2.42 2.9593 (19) 116
C11—H11⋯O1i 0.95 2.75 3.626 (2) 153
Symmetry code: (i) [x, y-1, z].
[Figure 2]
Figure 2
Packing diagram for 1 (viewed along the c-axis direction) showing C—H⋯O and C—H⋯N contacts as dashed lines.

Synthesis and crystallization

To a solution of p-cresol (0.1 mol) dissolved in 10 ml of di­methyl­sulfoxide,1-phenyl-5-chloro-3-methyl-1H-pyrazol-4-carbaldehyde (3.22 g, 0.1 mol) and potassium hydroxide (0.8 g, 0.1 mol) were added and the resulting solution was heated on a water bath for 5 h. The reaction mixture was cooled to room temperature and poured onto crushed ice. The solid that separated was filtered off and washed with water and the dried product was recrystallized from ethanol solution. The reaction scheme is shown in Fig. 3[link].

[Figure 3]
Figure 3
Reaction scheme.

Yield: 82%; m.p. 320–322 K; MS (m/z) 293.1 (M+ + 1). 1H NMR (400 MHz, CDCl3, δ p.p.m.), 2.22 (s, 3H, pyrazole meth­yl), 2.34 (s, 3H, o-tol­yloxy meth­yl), 6.93 (d, 2H, J = 8.3 Hz, Ar—H), 7.04 (d, 2H, J = 8.3 Hz, Ar—H), 7.23 (d, 1H, J = 7.3 Hz), 7.46 (d, 2H, J = 8.1 Hz, Ar—H), 7.81 (d, 2H, J = 8.1 Hz, Ar—H), 8.61 (s, 1H, aldehyde-H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C18H16N2O2
Mr 292.33
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 8.2745 (5), 7.9167 (6), 23.0663 (17)
β (°) 93.225 (4)
V (Å3) 1508.60 (18)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.33 × 0.29 × 0.21
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.560, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 22729, 4612, 3061
Rint 0.075
(sin θ/λ)max (Å−1) 0.717
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.150, 1.08
No. of reflections 4612
No. of parameters 201
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.24, −0.22
Computer programs: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2002[Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data

CCDC reference: 2207948

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622009245/hb4413sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622009245/hb4413Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622009245/hb4413Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXT (Sheldrick 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-Methyl-5-(4-methylphenoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde top
Crystal data top
C18H16N2O2F(000) = 616
Mr = 292.33Dx = 1.287 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.2745 (5) ÅCell parameters from 6530 reflections
b = 7.9167 (6) Åθ = 3.1–29.6°
c = 23.0663 (17) ŵ = 0.09 mm−1
β = 93.225 (4)°T = 100 K
V = 1508.60 (18) Å3Block, pale yellow
Z = 40.33 × 0.29 × 0.21 mm
Data collection top
Bruker APEXII CCD
diffractometer		3061 reflections with I > 2σ(I)
φ and ω scansRint = 0.075
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		θmax = 30.6°, θmin = 2.5°
Tmin = 0.560, Tmax = 0.746h = −11→11
22729 measured reflectionsk = −11→9
4612 independent reflectionsl = −32→32
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2283P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4612 reflectionsΔρmax = 0.24 e Å−3
201 parametersΔρmin = −0.21 e Å−3
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.

Refinement. All hydrogen atoms were placed geometrically and refined as riding atoms with their Uiso values 1.2 × (1.5 × for CH3) that of their attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.14639 (15)0.70581 (16)0.38374 (6)0.0644 (3)
O20.41488 (13)0.23801 (12)0.37711 (4)0.0434 (3)
N10.61932 (13)0.41501 (13)0.41767 (5)0.0370 (3)
N20.63851 (14)0.57702 (14)0.43941 (5)0.0395 (3)
C10.49777 (17)0.65200 (17)0.42911 (6)0.0388 (3)
C20.4761 (2)0.83049 (19)0.44777 (7)0.0502 (4)
H2A0.5764010.8709100.4677800.075*
H2B0.3876210.8367230.4741850.075*
H2C0.4502140.9011540.4136270.075*
C30.38270 (17)0.54160 (18)0.40121 (6)0.0398 (3)
C40.21536 (19)0.5708 (2)0.38257 (7)0.0492 (4)
H40.1543970.4764670.3682300.059*
C50.46660 (16)0.39239 (16)0.39555 (6)0.0373 (3)
C60.36301 (16)0.21805 (16)0.31822 (6)0.0358 (3)
C70.41496 (19)0.32023 (19)0.27473 (7)0.0453 (3)
H70.4868710.4116510.2831420.054*
C80.3587 (2)0.2851 (2)0.21804 (7)0.0510 (4)
H80.3934720.3532030.1871990.061*
C90.25337 (19)0.1535 (2)0.20582 (6)0.0473 (4)
H90.2145810.1334160.1668900.057*
C100.20347 (17)0.05002 (18)0.25005 (6)0.0424 (3)
C110.26116 (15)0.08271 (17)0.30678 (6)0.0372 (3)
H110.2304710.0119630.3375540.045*
C120.0879 (2)−0.0940 (3)0.23791 (8)0.0687 (5)
H12A0.086719−0.1236270.1966390.103*
H12B−0.021126−0.0601870.2478240.103*
H12C0.122673−0.1920350.2613680.103*
C130.75428 (16)0.30235 (16)0.42240 (6)0.0371 (3)
C140.87596 (18)0.3355 (2)0.46428 (7)0.0470 (3)
H140.8677800.4298490.4893870.056*
C151.0098 (2)0.2308 (2)0.46956 (8)0.0554 (4)
H151.0939060.2540840.4981860.067*
C161.0220 (2)0.0931 (2)0.43365 (8)0.0540 (4)
H161.1139770.0213730.4374200.065*
C170.8997 (2)0.0602 (2)0.39220 (8)0.0566 (4)
H170.907241−0.0356660.3677300.068*
C180.7662 (2)0.1650 (2)0.38573 (7)0.0505 (4)
H180.6835090.1430190.3564470.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0580 (7)0.0630 (8)0.0711 (8)0.0205 (6)−0.0064 (6)−0.0004 (6)
O20.0538 (6)0.0350 (5)0.0400 (5)−0.0067 (4)−0.0104 (4)−0.0001 (4)
N10.0410 (6)0.0327 (5)0.0367 (6)0.0002 (4)−0.0036 (4)−0.0047 (4)
N20.0464 (6)0.0325 (5)0.0391 (6)−0.0002 (5)−0.0018 (5)−0.0069 (5)
C10.0459 (7)0.0362 (7)0.0343 (7)0.0031 (6)0.0017 (5)−0.0008 (5)
C20.0614 (9)0.0379 (7)0.0512 (9)0.0061 (7)0.0014 (7)−0.0067 (6)
C30.0430 (7)0.0388 (7)0.0371 (7)0.0020 (6)−0.0023 (5)−0.0002 (5)
C40.0478 (8)0.0526 (9)0.0463 (8)0.0051 (7)−0.0060 (6)0.0003 (7)
C50.0431 (7)0.0343 (6)0.0337 (6)−0.0028 (5)−0.0051 (5)−0.0013 (5)
C60.0355 (6)0.0352 (6)0.0361 (6)0.0020 (5)−0.0026 (5)−0.0026 (5)
C70.0492 (8)0.0409 (7)0.0458 (8)−0.0069 (6)0.0023 (6)0.0007 (6)
C80.0635 (10)0.0480 (8)0.0422 (8)0.0023 (7)0.0080 (7)0.0061 (7)
C90.0554 (9)0.0496 (8)0.0364 (7)0.0078 (7)−0.0025 (6)−0.0052 (6)
C100.0400 (7)0.0435 (7)0.0431 (7)0.0011 (6)−0.0022 (5)−0.0084 (6)
C110.0362 (6)0.0374 (7)0.0378 (7)−0.0011 (5)0.0006 (5)−0.0018 (5)
C120.0738 (12)0.0718 (12)0.0589 (11)−0.0261 (10)−0.0100 (9)−0.0122 (9)
C130.0395 (7)0.0351 (6)0.0366 (7)0.0014 (5)0.0020 (5)0.0008 (5)
C140.0492 (8)0.0456 (8)0.0453 (8)0.0040 (6)−0.0061 (6)−0.0054 (6)
C150.0495 (9)0.0597 (10)0.0557 (9)0.0102 (7)−0.0088 (7)−0.0006 (8)
C160.0510 (9)0.0535 (9)0.0581 (10)0.0158 (7)0.0073 (7)0.0061 (7)
C170.0617 (10)0.0485 (9)0.0601 (10)0.0101 (7)0.0085 (8)−0.0112 (7)
C180.0515 (9)0.0487 (8)0.0507 (9)0.0049 (7)−0.0030 (7)−0.0125 (7)
Geometric parameters (Å, º) top
O1—C41.2129 (19)C8—C91.377 (2)
O2—C51.3555 (15)C9—H90.9500
O2—C61.4103 (16)C9—C101.389 (2)
N1—N21.3830 (15)C10—C111.3917 (19)
N1—C51.3478 (17)C10—C121.505 (2)
N1—C131.4285 (17)C11—H110.9500
N2—C11.3167 (18)C12—H12A0.9800
C1—C21.4909 (19)C12—H12B0.9800
C1—C31.4197 (19)C12—H12C0.9800
C2—H2A0.9800C13—C141.381 (2)
C2—H2B0.9800C13—C181.384 (2)
C2—H2C0.9800C14—H140.9500
C3—C41.445 (2)C14—C151.383 (2)
C3—C51.3800 (19)C15—H150.9500
C4—H40.9500C15—C161.376 (2)
C6—C71.376 (2)C16—H160.9500
C6—C111.3794 (18)C16—C171.377 (2)
C7—H70.9500C17—H170.9500
C7—C81.391 (2)C17—C181.383 (2)
C8—H80.9500C18—H180.9500
C5—O2—C6118.48 (10)C8—C9—C10120.45 (14)
N2—N1—C13118.56 (11)C10—C9—H9119.8
C5—N1—N2110.27 (11)C9—C10—C11118.70 (13)
C5—N1—C13131.16 (11)C9—C10—C12121.51 (14)
C1—N2—N1105.68 (11)C11—C10—C12119.79 (14)
N2—C1—C2119.63 (13)C6—C11—C10119.87 (13)
N2—C1—C3111.60 (12)C6—C11—H11120.1
C3—C1—C2128.76 (13)C10—C11—H11120.1
C1—C2—H2A109.5C10—C12—H12A109.5
C1—C2—H2B109.5C10—C12—H12B109.5
C1—C2—H2C109.5C10—C12—H12C109.5
H2A—C2—H2B109.5H12A—C12—H12B109.5
H2A—C2—H2C109.5H12A—C12—H12C109.5
H2B—C2—H2C109.5H12B—C12—H12C109.5
C1—C3—C4130.04 (13)C14—C13—N1118.10 (12)
C5—C3—C1103.98 (12)C14—C13—C18120.17 (13)
C5—C3—C4125.97 (13)C18—C13—N1121.72 (13)
O1—C4—C3125.34 (15)C13—C14—H14120.1
O1—C4—H4117.3C13—C14—C15119.77 (14)
C3—C4—H4117.3C15—C14—H14120.1
O2—C5—C3130.53 (13)C14—C15—H15119.8
N1—C5—O2120.75 (12)C16—C15—C14120.46 (15)
N1—C5—C3108.45 (11)C16—C15—H15119.8
C7—C6—O2123.07 (12)C15—C16—H16120.3
C7—C6—C11121.98 (13)C15—C16—C17119.48 (15)
C11—C6—O2114.90 (12)C17—C16—H16120.3
C6—C7—H7121.1C16—C17—H17119.6
C6—C7—C8117.77 (14)C16—C17—C18120.83 (15)
C8—C7—H7121.1C18—C17—H17119.6
C7—C8—H8119.4C13—C18—H18120.4
C9—C8—C7121.20 (14)C17—C18—C13119.28 (15)
C9—C8—H8119.4C17—C18—H18120.4
C8—C9—H9119.8
O2—C6—C7—C8178.25 (13)C5—N1—C13—C14−157.00 (15)
O2—C6—C11—C10−179.47 (12)C5—N1—C13—C1824.1 (2)
N1—N2—C1—C2179.50 (12)C5—C3—C4—O1−174.07 (16)
N1—N2—C1—C30.71 (15)C6—O2—C5—N1−118.79 (14)
N1—C13—C14—C15−178.97 (14)C6—O2—C5—C367.98 (19)
N1—C13—C18—C17179.89 (14)C6—C7—C8—C90.5 (2)
N2—N1—C5—O2−173.26 (12)C7—C6—C11—C10−2.3 (2)
N2—N1—C5—C31.32 (16)C7—C8—C9—C10−1.4 (2)
N2—N1—C13—C1421.84 (19)C8—C9—C10—C110.4 (2)
N2—N1—C13—C18−157.01 (13)C8—C9—C10—C12179.67 (16)
N2—C1—C3—C4179.55 (14)C9—C10—C11—C61.4 (2)
N2—C1—C3—C50.05 (16)C11—C6—C7—C81.3 (2)
C1—C3—C4—O16.5 (3)C12—C10—C11—C6−177.89 (15)
C1—C3—C5—O2173.04 (14)C13—N1—N2—C1179.67 (11)
C1—C3—C5—N1−0.83 (15)C13—N1—C5—O25.7 (2)
C2—C1—C3—C40.9 (3)C13—N1—C5—C3−179.76 (13)
C2—C1—C3—C5−178.59 (14)C13—C14—C15—C16−0.5 (3)
C4—C3—C5—O2−6.5 (2)C14—C13—C18—C171.1 (2)
C4—C3—C5—N1179.64 (14)C14—C15—C16—C170.1 (3)
C5—O2—C6—C725.02 (19)C15—C16—C17—C180.9 (3)
C5—O2—C6—C11−157.83 (12)C16—C17—C18—C13−1.5 (3)
C5—N1—N2—C1−1.26 (15)C18—C13—C14—C15−0.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18···O20.952.422.9593 (19)116
C11—H11···O1i0.952.753.626 (2)153
Symmetry code: (i) x, y−1, z.
 

Acknowledgements

SDA and HAN are grateful to Mysore & Mangalore Universities, respectively for the provision of research facilities.

Funding information

HSY and BK are grateful to UGC, New Delhi, for the award of BSR Faculty Fellowships.

References

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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.

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ISSN: 2414-3146
Volume 7| Part 9| September 2022| x220924
https://doi.org/10.1107/S2414314622009245
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