Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share

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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 8| Part 5| May 2023| x230455
https://doi.org/10.1107/S2414314623004558

(E)-5-(4-Meth­­oxy­phen­yl)-N′-(2-oxoindolin-3-yl­­idene)-1-phenyl-1H-pyrazole-3-carbohydrazide

crossmark logo
Bakr F. Abdel-Wahab,a Abdelbasset A. Farahat,b,c Mohamed S. Bekheit,d Emad Yousif,e Benson M. Kariukif and Gamal A. El-Hitig*

aApplied Organic Chemistry Department, Chemical Industries Research Institute, National Research Centre, Dokki, Giza 12622, Egypt, bMaster of Pharmaceutical Sciences Program, California Northstate University, Elk Grove, CA 95757, USA, cDepartment of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt, dDepartment of Pesticide Chemistry, National Research Centre, Dokki, Giza 12622, Egypt, eDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, United Kingdom, and gDepartment of Optometry, College of Applied Medical Sciences, King Saud University, Riyadh 11433, Saudi Arabia
*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 20 April 2023; accepted 23 May 2023; online 26 May 2023)

This article is part of a collection of articles to commemorate the founding of the African Crystallographic Association and the 75th anniversary of the IUCr.

The asymmetric unit of the title compound, C25H19N5O3, is composed of two independent mol­ecules with slightly different conformations. The extended structure features N—H⋯O hydrogen bonds as well as π–π inter­actions.

CCDC reference: 2235858

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The synthesis of hydrazides and hydrazones is of inter­est because of their involvement in various synthetic transformations. In addition, they have potential pharmacological applications (see, for example, Afsah et al., 2016[Afsah, E. M., Elmorsy, S. S., Abdelmageed, S. M. & Zaki, Z. E. (2016). Z. Naturforsch. B, 71, 1147-1157.]). Isatin-containing heterocycles also exhibit biological activities, such as anti­convulsant, anti­microbial and anti­oxidant properties (see, for example, Kaur et al., 2016[Kaur, M., Singh, M., Chadha, N. & Silakari, O. (2016). Eur. J. Med. Chem. 123, 858-894.]). The most common synthetic methods for isatins involve the oxidation of indoles (Zi et al., 2014[Zi, Y., Cai, Z.-J., Wang, S.-Y. & Ji, S.-J. (2014). Org. Lett. 16, 3094-3097.]), oxindoles (Wei et al., 2017[Wei, W.-T., Ying, W.-W., Zhu, W.-M., Wu, Y., Huang, Y.-L., Cao, Y.-Q., Wang, Y.-N. & Liang, H. (2017). Synlett, 28, 2307-2310.]; Ying et al., 2018[Ying, W.-W., Zhu, W.-M., Liang, H. & Wei, W.-T. (2018). Synlett, 29, 215-218.]) and amino­aceto­phenones (Qian et al., 2017[Qian, P., Su, J.-H., Wang, Y., Bi, M., Zha, Z. & Wang, Z. (2017). J. Org. Chem. 82, 6434-6440.]). Pyrazoles have several medicinal uses and can act as analgesics and anti­pyretics (see, for example, Rios & Portilla, 2022[Ríos, M.-C. & Portilla, J. (2022). Chemistry, 4, 940-968.]). Many synthetic procedures have been reported for the synthesis of pyrazoles (see, for example, Zora et al., 2011[Zora, M., Kivrak, A. & Yazici, C. (2011). J. Org. Chem. 76, 6726-6742.]; Karrouchi et al., 2018[Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y. N., Al-aizari, F. A. & Ansar, M. (2018). Molecules, 23, 134131.]; Li et al., 2021[Li, X., Yu, Y. & Tu, Z. (2021). Molecules, 26, 1202.]). Recently, we have been investigating the synthesis and structure elucidation of various heterocycles. The current work describes the synthesis and the crystal structure of a hydrazone containing both isatin and pyrazole moieties using a simple procedure.

The crystal structure of the title compound, C25H19N5O3, contains two independent mol­ecules, M1 and M2 (Fig. 1[link]). Each mol­ecule comprises indole-2-one (M1A: C1–C8, N1, O1 and M2A: C26–C33, N6, O4), formohydrazide (M1B: C9, N2, N3, O2 and M2B: C34, N7, N8, O5), pyrazole (M1C: C10–C12, N4, N5 and M2C: C35–C37, N9, N10), meth­oxy­benzene (M1D: C13–C19, O3 and M2D: C38–C44, O6) and phenyl (M1E: C20–C25 and M2E: C45–C50) moieties.

[Figure 1]
Figure 1
An ORTEP representation of the asymmetric unit of the title compound showing 50% probability atomic displacement parameters. Only the major disorder component of the disordered meth­oxy­benzene group of mol­ecule M2 is shown.

In both mol­ecules, the indole-2-one, formohydrazide and pyrazole groups are close to coplanar: the twist angles M1A/M1B and M1B/M1C are 5.0 (1) and 10.7 (1)°, respectively, for mol­ecule M1 and the corresponding angles M2A/M2B and M2B/M2C for mol­ecule M2 are 4.1 (2) and 9.7 (2)°, respectively. The near coplanarity of the indole-2-one and formohydrazide groups is similar to that observed for the related 1-(4-meth­oxy­phen­yl)-5-methyl-N′-(2-oxoindolin-3-yl­idene)-1H-1,2,3-triazole-4-carbohydrazide, 3 (Kariuki et al., 2022[Kariuki, B. M., Abdel-Wahab, B. F., Farahat, A. A. & El-Hiti, G. A. (2022). Molbank, 2022, M1374.]) and 1-(4-fluoro­phen­yl)-N′-(2-oxoindolin-3-yl­idene)-5-phenyl-1H-1,2,3-triazole-4-carbohydrazide, 4 (Mohamed et al., 2023[Mohamed, H. A., Bekheit, M. S., Ewies, E. F., Awad, H. M., Betz, R., Hosten, E. C. & Abdel-Wahab, B. F. (2023). J. Mol. Struct. 1274, 134415.]).

The meth­oxy­benzene and phenyl groups deviate from the plane of the indole-2-one and formohydrazide groups. The twist angles M1C/M1D and M1C/M1E are 51.9 (2) and 55.8 (1)°, respectively, for mol­ecule M1 while M2C/M2D and M2C/M2E are 51.7 (2) and 57.7 (1)°, respectively, for mol­ecule M2. The twists of the two aromatic rings from the plane of the pyrazole group is of the same order as observed in 3 (Mohamed et al., 2023[Mohamed, H. A., Bekheit, M. S., Ewies, E. F., Awad, H. M., Betz, R., Hosten, E. C. & Abdel-Wahab, B. F. (2023). J. Mol. Struct. 1274, 134415.]) as well as in 4-{3-[2-(4-meth­oxy­benzyl­idene)hydrazine-1-carbon­yl]-5-(4-meth­oxy­phen­yl)-1H-pyrazol-1-yl}benzene­sulfonamide and 4-{5-(4-bromo­phen­yl)-3-[2-(4-methyl­benzyl­idene)hydrazine-1-carbon­yl]-1H-pyrazol-1-yl}benzene­sulfonamide, 5 (Lu et al., 2016[Lu, X.-Y., Wang, Z.-C., Wei, T., Yan, X.-Q., Wang, P.-F. & Zhu, H.-L. (2016). RSC Adv. 6, 22917-22935.]). Intra­molecular N—H⋯O hydrogen bonds (Table 1[link]) contribute to the observed mol­ecular planarity. Similar intra­molecular N—H⋯O hydrogen bonds also occur in 3 and 4.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O5i 0.86 2.13 2.8594 (16) 142
N3—H3⋯O1 0.86 2.07 2.7419 (17) 135
N6—H6A⋯O2 0.86 2.13 2.8512 (17) 142
N8—H8A⋯O4 0.86 2.07 2.7396 (16) 134
C5—H5⋯O5i 0.93 2.49 3.172 (2) 130
C30—H30⋯O2 0.93 2.52 3.187 (2) 129
C36—H36⋯O3ii 0.93 2.44 3.330 (2) 159
Symmetry codes: (i) x, y+1, z; (ii) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

In the extended structure of the title compound, the mol­ecules form layers oriented parallel to (102) (Fig. 2[link]a). Inter­molecular N—H⋯O hydrogen bonds (Table 1[link]) occur within the layers. In the layers, aromatic ring edge-to-face inter­actions occur with ring centroid-to-centroid distances in the range 5.4–5.7 Å (Fig. 2[link]b). Inter­actions of the type π–π between rings are also observed with centroid–centroid distances of about 4.17 Å.

[Figure 2]
Figure 2
(a) Crystal packing for the title compound and (b) a layer showing the edge-to-face inter­actions (red dotted lines), π–π inter­actions (blue) and N—H⋯O hydrogen bonds (green).

Synthesis and crystallization

A mixture of 5-(4-meth­oxy­phen­yl)-1-phenyl-1H-pyrazole-3-carbohydrazide 1 (0.62 g, 2.0 mmol) and isatin 2 (0.30 g, 2.0 mmol) in dry EtOH (15 ml) containing a catalytic qu­antity of concentrated HCl (0.1 ml) was refluxed for 2 h. The mixture was left to cool to 20°C and the orange solid produced was collected by filtration. The product was washed with EtOH, dried, and recrystallized from DMF to give the title compound in 90% yield, m.p. 280–281°C. 1H NMR (p.p.m.): 3.72 (s, 3H, OMe), 6.89 (d, 9.1 Hz, 2H, Ar), 6.92 (d, 1H, 7.7 Hz, Ar), 7.08 (t, 7.7 Hz, 1H, Ar), 7.15 (s, 1H, pyrazol­yl), 7.18 (d, 9.1 Hz, 2H, Ar), 7.33–7.36 (m, 3H, Ar), 7.44–7.48 (m, 3H, Ar), 7.58 (d, 7.7 Hz, 1H, Ar), 11.17 (s, exch., 1H, NH), 14.08 (s, exch., 1H, NH). 13C NMR (p.p.m.): 55.7, 108.4, 111.6, 114.7, 120.5, 121.6, 123.1, 126.2, 129.2, 129.3, 129.8, 130.6, 132.2, 138.3, 139.8, 143.1, 145.5, 145.7, 158.4, 160.2, 163.1. Analysis calculated for C25H19N5O3 (437.46): C, 68.64; H, 4.38; N, 16.01. Found: C, 68.77; H, 4.47; N, 16.13%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The meth­oxy­benzene group of one mol­ecule is disordered and was modelled with two components of 0.66 (2) and 0.34 (2) occupancy.

Table 2
Experimental details

Crystal data
Chemical formula C25H19N5O3
Mr 437.45
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 10.8353 (2), 13.3587 (2), 30.3697 (4)
β (°) 91.838 (1)
V (Å3) 4393.62 (12)
Z 8
Radiation type Cu Kα
μ (mm−1) 0.74
Crystal size (mm) 0.28 × 0.24 × 0.13
 
Data collection
Diffractometer SuperNova, Dual, Cu at home/near, Atlas
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2022[Rigaku OD. (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Oxford, England.])
Tmin, Tmax 0.663, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 33362, 8632, 6902
Rint 0.027
(sin θ/λ)max (Å−1) 0.620
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.122, 1.02
No. of reflections 8632
No. of parameters 671
No. of restraints 389
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.16, −0.15
Computer programs: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022[Rigaku OD. (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Oxford, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2020[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.]) and ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data

CCDC reference: 2235858

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623004558/hb4430sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623004558/hb4430Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623004558/hb4430Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).

(E)-5-(4-Methoxyphenyl)-N'-(2-oxoindolin-3-ylidene)-1-phenyl-1H-pyrazole-3-carbohydrazide top
Crystal data top
C25H19N5O3F(000) = 1824
Mr = 437.45Dx = 1.323 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 10.8353 (2) ÅCell parameters from 14981 reflections
b = 13.3587 (2) Åθ = 4.4–72.8°
c = 30.3697 (4) ŵ = 0.74 mm−1
β = 91.838 (1)°T = 293 K
V = 4393.62 (12) Å3Needle, yellow
Z = 80.28 × 0.24 × 0.13 mm
Data collection top
SuperNova, Dual, Cu at home/near, Atlas
diffractometer		6902 reflections with I > 2σ(I)
ω scansRint = 0.027
Absorption correction: gaussian
(Crysalispro; Rigaku OD, 2022)		θmax = 72.8°, θmin = 3.6°
Tmin = 0.663, Tmax = 1.000h = −11→13
33362 measured reflectionsk = −16→16
8632 independent reflectionsl = −37→28
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0662P)2 + 0.4435P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
8632 reflectionsΔρmax = 0.16 e Å−3
671 parametersΔρmin = −0.15 e Å−3
389 restraints
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
xyzUiso*/UeqOcc. (<1)
C10.52252 (15)0.83217 (11)0.32663 (5)0.0592 (3)
C20.52711 (14)0.72003 (11)0.32210 (4)0.0537 (3)
C30.60695 (14)0.69953 (11)0.28547 (5)0.0555 (3)
C40.64382 (14)0.79218 (11)0.26934 (5)0.0572 (3)
C50.72114 (16)0.79927 (13)0.23416 (6)0.0677 (4)
H50.7447640.8610070.2230640.081*
C60.76180 (18)0.71073 (14)0.21621 (6)0.0742 (5)
H60.8151960.7133270.1928620.089*
C70.72579 (18)0.61836 (14)0.23178 (6)0.0764 (5)
H70.7548930.5602870.2187870.092*
C80.64635 (17)0.61160 (12)0.26675 (5)0.0669 (4)
H80.6206510.5497890.2771480.080*
C90.34347 (14)0.62106 (11)0.40400 (5)0.0550 (3)
C100.28695 (13)0.66435 (11)0.44319 (4)0.0540 (3)
C110.22281 (14)0.61278 (12)0.47516 (5)0.0579 (3)
H110.2014990.5453390.4750960.070*
C120.19783 (14)0.68269 (11)0.50672 (5)0.0568 (3)
C130.14081 (14)0.66994 (11)0.54983 (4)0.0557 (3)
C140.02927 (15)0.61940 (12)0.55308 (5)0.0627 (4)
H14−0.0111800.5960600.5276350.075*
C15−0.02234 (15)0.60332 (13)0.59332 (5)0.0642 (4)
H15−0.0974260.5699870.5948760.077*
C160.03778 (14)0.63689 (11)0.63153 (5)0.0565 (3)
C170.14915 (14)0.68614 (12)0.62901 (5)0.0603 (4)
H170.1901440.7082920.6545640.072*
C180.19988 (14)0.70257 (12)0.58833 (5)0.0609 (4)
H180.2748640.7360860.5868500.073*
C190.0467 (2)0.63903 (18)0.71002 (5)0.0877 (6)
H19A0.1260110.6069460.7099740.132*
H19B0.0011090.6147490.7344100.132*
H19C0.0577060.7100980.7127370.132*
O3−0.01949 (11)0.61720 (10)0.66988 (3)0.0730 (3)
C200.24421 (16)0.86755 (11)0.51263 (5)0.0606 (4)
C210.35404 (19)0.91566 (14)0.52136 (7)0.0795 (5)
H210.4280340.8863740.5135090.095*
C220.3541 (2)1.00840 (16)0.54202 (8)0.0942 (6)
H220.4284471.0409200.5483360.113*
C230.2460 (2)1.05185 (15)0.55304 (7)0.0898 (6)
H230.2463161.1146630.5662420.108*
C240.1367 (2)1.00314 (16)0.54470 (7)0.0913 (6)
H240.0631601.0326310.5529360.110*
C250.13386 (19)0.91034 (15)0.52413 (6)0.0787 (5)
H250.0593200.8777350.5182360.094*
C260.54022 (15)0.33380 (11)0.32501 (5)0.0601 (3)
C270.53916 (14)0.22196 (11)0.33016 (5)0.0550 (3)
C280.46467 (15)0.20092 (11)0.36808 (5)0.0586 (3)
C290.42502 (16)0.29316 (12)0.38402 (5)0.0629 (4)
C300.35281 (19)0.29935 (14)0.42042 (6)0.0774 (5)
H300.3269150.3608490.4311130.093*
C310.3203 (2)0.21097 (15)0.44043 (6)0.0851 (6)
H310.2718960.2132530.4651380.102*
C320.3577 (2)0.11927 (15)0.42481 (6)0.0822 (5)
H320.3338200.0610350.4389970.099*
C330.43062 (18)0.11295 (13)0.38810 (6)0.0711 (4)
H330.4557020.0512590.3773670.085*
C340.71499 (14)0.12317 (11)0.24600 (5)0.0549 (3)
C350.79638 (14)0.16684 (11)0.21296 (4)0.0543 (3)
C360.87553 (15)0.11368 (12)0.18615 (5)0.0598 (4)
H360.8845970.0445950.1843130.072*
C370.93705 (14)0.18535 (11)0.16310 (5)0.0565 (3)
C381.0266 (9)0.1775 (9)0.1271 (3)0.0520 (12)0.66 (2)
C391.1282 (9)0.1166 (8)0.1344 (3)0.0658 (14)0.66 (2)
H391.1407690.0867170.1618130.079*0.66 (2)
C401.2120 (8)0.0992 (7)0.1015 (3)0.0681 (13)0.66 (2)
H401.2792340.0570510.1067350.082*0.66 (2)
C411.1947 (6)0.1448 (5)0.0612 (2)0.0566 (11)0.66 (2)
C421.0961 (7)0.2093 (7)0.0542 (2)0.0561 (11)0.66 (2)
H421.0860000.2420430.0272930.067*0.66 (2)
C431.0129 (8)0.2254 (8)0.0868 (3)0.0535 (11)0.66 (2)
H430.9468600.2688710.0817290.064*0.66 (2)
C441.3854 (6)0.0877 (11)0.0336 (3)0.099 (2)0.66 (2)
H44A1.4320100.1291680.0539150.148*0.66 (2)
H44B1.4278620.0829290.0064470.148*0.66 (2)
H44C1.3765450.0220380.0460140.148*0.66 (2)
O61.2671 (7)0.1303 (5)0.0256 (2)0.0755 (11)0.66 (2)
C38B1.0365 (18)0.1668 (18)0.1326 (6)0.053 (2)0.34 (2)
C39B1.1343 (16)0.1024 (14)0.1406 (5)0.0577 (18)0.34 (2)
H39B1.1415680.0700450.1676710.069*0.34 (2)
C40B1.2218 (13)0.0848 (12)0.1093 (5)0.0607 (18)0.34 (2)
H40B1.2890630.0433640.1156250.073*0.34 (2)
C41B1.2078 (11)0.1296 (9)0.0685 (4)0.0589 (18)0.34 (2)
C42B1.1093 (14)0.1924 (12)0.0595 (5)0.060 (2)0.34 (2)
H42B1.0997950.2219760.0319100.073*0.34 (2)
C43B1.0247 (16)0.2114 (15)0.0916 (6)0.058 (2)0.34 (2)
H43B0.9590460.2546380.0855870.069*0.34 (2)
C44B1.3891 (12)0.0531 (12)0.0426 (7)0.089 (3)0.34 (2)
H44D1.4368290.0779740.0674310.134*0.34 (2)
H44E1.4393820.0517940.0171490.134*0.34 (2)
H44F1.360994−0.0134640.0487980.134*0.34 (2)
O6B1.2863 (12)0.1161 (11)0.0344 (4)0.076 (2)0.34 (2)
C450.93673 (15)0.37295 (11)0.16561 (5)0.0583 (4)
C461.06071 (18)0.39405 (15)0.17271 (6)0.0735 (4)
H461.1140350.3455990.1843660.088*
C471.1044 (2)0.48796 (18)0.16229 (7)0.0912 (6)
H471.1877120.5029160.1666520.109*
C481.0248 (2)0.55904 (16)0.14551 (8)0.0948 (7)
H481.0544190.6222410.1385180.114*
C490.9022 (2)0.53768 (15)0.13898 (8)0.0929 (6)
H490.8488590.5866980.1278690.111*
C500.85682 (18)0.44350 (13)0.14879 (6)0.0742 (5)
H500.7736220.4286060.1440260.089*
N10.59191 (13)0.86917 (9)0.29427 (4)0.0644 (3)
H10.6029620.9319520.2895180.077*
N20.47247 (12)0.65335 (9)0.34518 (4)0.0556 (3)
N30.40306 (12)0.68823 (9)0.37855 (4)0.0567 (3)
H30.3970580.7514390.3834140.068*
N40.30144 (12)0.76075 (10)0.45310 (4)0.0589 (3)
N50.24509 (12)0.77127 (9)0.49202 (4)0.0581 (3)
N60.47120 (14)0.37071 (10)0.35775 (5)0.0681 (4)
H6A0.4574010.4333310.3619420.082*
N70.59252 (12)0.15611 (9)0.30643 (4)0.0557 (3)
N80.66029 (12)0.19096 (9)0.27276 (4)0.0564 (3)
H8A0.6684720.2542060.2684390.068*
N90.80578 (12)0.26548 (9)0.20751 (4)0.0564 (3)
N100.89251 (12)0.27560 (9)0.17665 (4)0.0564 (3)
O10.46685 (13)0.87878 (8)0.35461 (4)0.0761 (3)
O20.34031 (12)0.53157 (8)0.39661 (4)0.0713 (3)
O40.59503 (12)0.38076 (8)0.29704 (4)0.0736 (3)
O50.70216 (12)0.03351 (8)0.24977 (4)0.0735 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0688 (9)0.0552 (8)0.0545 (8)−0.0004 (7)0.0176 (7)−0.0021 (6)
C20.0599 (8)0.0551 (8)0.0468 (7)0.0024 (6)0.0134 (6)0.0011 (6)
C30.0604 (8)0.0578 (8)0.0491 (7)0.0024 (6)0.0144 (6)0.0021 (6)
C40.0612 (8)0.0583 (8)0.0528 (7)−0.0007 (6)0.0140 (6)−0.0007 (6)
C50.0739 (10)0.0675 (9)0.0632 (9)−0.0056 (8)0.0256 (8)0.0027 (7)
C60.0785 (11)0.0798 (11)0.0663 (10)0.0018 (8)0.0332 (8)0.0023 (8)
C70.0900 (12)0.0688 (10)0.0724 (10)0.0117 (9)0.0342 (9)−0.0025 (8)
C80.0804 (10)0.0588 (9)0.0632 (9)0.0068 (7)0.0265 (8)0.0026 (7)
C90.0601 (8)0.0550 (8)0.0506 (7)0.0054 (6)0.0152 (6)0.0013 (6)
C100.0600 (8)0.0565 (8)0.0465 (7)0.0052 (6)0.0149 (6)0.0011 (6)
C110.0662 (8)0.0589 (8)0.0495 (7)−0.0014 (6)0.0149 (6)0.0010 (6)
C120.0606 (8)0.0626 (8)0.0480 (7)0.0008 (6)0.0144 (6)0.0032 (6)
C130.0621 (8)0.0609 (8)0.0450 (7)−0.0003 (6)0.0141 (6)0.0021 (6)
C140.0693 (9)0.0733 (10)0.0459 (7)−0.0107 (7)0.0078 (6)−0.0003 (6)
C150.0634 (9)0.0755 (10)0.0543 (8)−0.0149 (7)0.0112 (7)0.0013 (7)
C160.0650 (8)0.0597 (8)0.0460 (7)−0.0032 (6)0.0169 (6)0.0005 (6)
C170.0667 (9)0.0688 (9)0.0459 (7)−0.0077 (7)0.0083 (6)−0.0030 (6)
C180.0574 (8)0.0728 (9)0.0532 (8)−0.0082 (7)0.0121 (6)0.0008 (7)
C190.0961 (13)0.1231 (16)0.0450 (8)−0.0197 (12)0.0185 (8)−0.0056 (9)
O30.0809 (7)0.0924 (8)0.0469 (5)−0.0197 (6)0.0211 (5)−0.0014 (5)
C200.0778 (10)0.0571 (8)0.0480 (7)0.0049 (7)0.0183 (7)0.0017 (6)
C210.0833 (12)0.0680 (10)0.0885 (12)−0.0030 (9)0.0238 (10)−0.0084 (9)
C220.1095 (16)0.0710 (12)0.1028 (16)−0.0114 (11)0.0159 (12)−0.0112 (11)
C230.1319 (19)0.0631 (10)0.0750 (12)0.0113 (12)0.0143 (12)−0.0078 (9)
C240.1104 (16)0.0816 (13)0.0831 (13)0.0319 (12)0.0216 (11)−0.0075 (10)
C250.0813 (11)0.0792 (11)0.0764 (11)0.0142 (9)0.0147 (9)−0.0068 (9)
C260.0657 (9)0.0563 (8)0.0591 (8)0.0036 (7)0.0163 (7)0.0006 (6)
C270.0606 (8)0.0555 (8)0.0497 (7)0.0027 (6)0.0153 (6)0.0009 (6)
C280.0672 (9)0.0594 (8)0.0503 (7)0.0046 (7)0.0167 (6)−0.0010 (6)
C290.0697 (9)0.0633 (9)0.0567 (8)0.0074 (7)0.0176 (7)−0.0012 (7)
C300.0917 (12)0.0751 (11)0.0672 (10)0.0139 (9)0.0314 (9)−0.0039 (8)
C310.1029 (14)0.0889 (13)0.0661 (10)0.0103 (10)0.0427 (10)0.0021 (9)
C320.1050 (14)0.0753 (11)0.0687 (10)0.0029 (10)0.0392 (10)0.0087 (8)
C330.0886 (11)0.0635 (9)0.0629 (9)0.0047 (8)0.0290 (8)0.0023 (7)
C340.0640 (8)0.0540 (8)0.0476 (7)−0.0008 (6)0.0162 (6)0.0017 (6)
C350.0627 (8)0.0551 (8)0.0461 (7)−0.0029 (6)0.0160 (6)−0.0005 (6)
C360.0701 (9)0.0557 (8)0.0549 (8)0.0015 (7)0.0214 (7)0.0000 (6)
C370.0616 (8)0.0604 (8)0.0483 (7)−0.0016 (6)0.0151 (6)−0.0018 (6)
C380.056 (2)0.056 (3)0.046 (3)−0.0001 (14)0.0142 (19)0.0002 (19)
C390.073 (2)0.074 (3)0.050 (2)0.009 (2)0.0096 (17)0.0135 (17)
C400.0618 (19)0.078 (3)0.065 (3)0.0170 (17)0.0098 (18)0.0058 (19)
C410.0548 (19)0.067 (2)0.0491 (18)−0.0030 (16)0.0123 (14)−0.0025 (15)
C420.0629 (19)0.061 (2)0.0455 (19)−0.0002 (14)0.0121 (14)0.0042 (15)
C430.057 (2)0.057 (3)0.0468 (19)0.0022 (14)0.0097 (15)0.0048 (15)
C440.066 (2)0.150 (6)0.081 (3)0.018 (3)0.0134 (19)−0.015 (4)
O60.062 (2)0.107 (2)0.059 (2)0.0102 (14)0.0207 (15)−0.0021 (15)
C38B0.058 (3)0.057 (4)0.045 (3)−0.003 (3)0.009 (3)0.004 (3)
C39B0.059 (3)0.062 (4)0.053 (4)0.008 (2)0.014 (3)0.010 (3)
C40B0.054 (3)0.068 (4)0.061 (3)0.005 (3)0.011 (3)0.004 (3)
C41B0.054 (3)0.068 (3)0.055 (3)0.004 (2)0.017 (3)−0.003 (3)
C42B0.072 (4)0.064 (4)0.046 (3)0.001 (3)0.015 (3)0.007 (3)
C43B0.060 (3)0.059 (4)0.055 (4)0.010 (3)0.010 (3)0.000 (3)
C44B0.065 (4)0.113 (7)0.090 (6)0.019 (4)0.030 (4)−0.017 (5)
O6B0.063 (4)0.105 (4)0.062 (4)0.013 (3)0.026 (3)−0.005 (3)
C450.0724 (9)0.0571 (8)0.0467 (7)−0.0090 (7)0.0226 (6)−0.0036 (6)
C460.0792 (11)0.0818 (11)0.0599 (9)−0.0162 (9)0.0080 (8)−0.0003 (8)
C470.0998 (15)0.0941 (15)0.0808 (12)−0.0401 (12)0.0173 (11)−0.0070 (11)
C480.1280 (19)0.0671 (11)0.0918 (14)−0.0281 (12)0.0423 (13)−0.0041 (10)
C490.1182 (17)0.0608 (10)0.1020 (15)0.0036 (11)0.0387 (13)0.0094 (10)
C500.0791 (11)0.0633 (9)0.0819 (11)0.0010 (8)0.0278 (9)0.0026 (8)
N10.0813 (9)0.0516 (7)0.0619 (7)−0.0047 (6)0.0264 (6)−0.0014 (5)
N20.0647 (7)0.0553 (6)0.0479 (6)0.0042 (5)0.0181 (5)0.0000 (5)
N30.0703 (7)0.0520 (6)0.0490 (6)0.0028 (5)0.0217 (5)0.0004 (5)
N40.0690 (7)0.0611 (7)0.0478 (6)0.0031 (6)0.0217 (5)0.0010 (5)
N50.0697 (7)0.0581 (7)0.0477 (6)0.0011 (6)0.0205 (5)0.0000 (5)
N60.0822 (9)0.0546 (7)0.0692 (8)0.0079 (6)0.0271 (7)−0.0019 (6)
N70.0645 (7)0.0559 (7)0.0477 (6)0.0004 (5)0.0186 (5)0.0017 (5)
N80.0676 (7)0.0516 (6)0.0513 (6)−0.0004 (5)0.0228 (5)0.0024 (5)
N90.0650 (7)0.0571 (7)0.0484 (6)−0.0046 (5)0.0212 (5)−0.0006 (5)
N100.0656 (7)0.0553 (7)0.0496 (6)−0.0053 (5)0.0206 (5)−0.0016 (5)
O10.1001 (9)0.0573 (6)0.0732 (7)0.0007 (6)0.0383 (6)−0.0079 (5)
O20.0912 (8)0.0544 (6)0.0703 (7)−0.0001 (5)0.0347 (6)−0.0019 (5)
O40.0886 (8)0.0566 (6)0.0777 (7)0.0020 (5)0.0337 (6)0.0079 (5)
O50.1010 (9)0.0524 (6)0.0696 (7)−0.0023 (5)0.0404 (6)0.0010 (5)
Geometric parameters (Å, º) top
C1—O11.2275 (18)C31—H310.9300
C1—N11.3500 (19)C32—C331.390 (2)
C1—C21.505 (2)C32—H320.9300
C2—N21.2892 (18)C33—H330.9300
C2—C31.4568 (18)C34—O51.2117 (18)
C3—C81.379 (2)C34—N81.3650 (18)
C3—C41.394 (2)C34—C351.4771 (18)
C4—C51.382 (2)C35—N91.3323 (19)
C4—N11.4053 (19)C35—C361.3955 (19)
C5—C61.380 (2)C36—C371.371 (2)
C5—H50.9300C36—H360.9300
C6—C71.382 (3)C37—N101.3670 (19)
C6—H60.9300C37—C38B1.464 (14)
C7—C81.391 (2)C37—C381.489 (7)
C7—H70.9300C38—C391.380 (4)
C8—H80.9300C38—C431.384 (4)
C9—O21.2166 (18)C39—C401.391 (4)
C9—N31.3607 (18)C39—H390.9300
C9—C101.4741 (18)C40—C411.374 (4)
C10—N41.331 (2)C40—H400.9300
C10—C111.3941 (19)C41—O61.372 (4)
C11—C121.371 (2)C41—C421.384 (4)
C11—H110.9300C42—C431.378 (4)
C12—N51.3698 (19)C42—H420.9300
C12—C131.4754 (18)C43—H430.9300
C13—C181.385 (2)C44—O61.416 (5)
C13—C141.391 (2)C44—H44A0.9600
C14—C151.377 (2)C44—H44B0.9600
C14—H140.9300C44—H44C0.9600
C15—C161.387 (2)C38B—C39B1.380 (7)
C15—H150.9300C38B—C43B1.382 (7)
C16—O31.3627 (16)C39B—C40B1.385 (6)
C16—C171.379 (2)C39B—H39B0.9300
C17—C181.3858 (19)C40B—C41B1.378 (7)
C17—H170.9300C40B—H40B0.9300
C18—H180.9300C41B—O6B1.373 (6)
C19—O31.425 (2)C41B—C42B1.378 (7)
C19—H19A0.9600C42B—C43B1.384 (6)
C19—H19B0.9600C42B—H42B0.9300
C19—H19C0.9600C43B—H43B0.9300
C20—C211.371 (3)C44B—O6B1.412 (7)
C20—C251.380 (2)C44B—H44D0.9600
C20—N51.4305 (19)C44B—H44E0.9600
C21—C221.389 (3)C44B—H44F0.9600
C21—H210.9300C45—C501.368 (3)
C22—C231.359 (3)C45—C461.383 (2)
C22—H220.9300C45—N101.4294 (18)
C23—C241.368 (3)C46—C471.381 (3)
C23—H230.9300C46—H460.9300
C24—C251.388 (3)C47—C481.370 (3)
C24—H240.9300C47—H470.9300
C25—H250.9300C48—C491.367 (3)
C26—O41.2249 (18)C48—H480.9300
C26—N61.3559 (19)C49—C501.387 (3)
C26—C271.502 (2)C49—H490.9300
C27—N71.2862 (18)C50—H500.9300
C27—C281.4545 (19)N1—H10.8600
C28—C331.379 (2)N2—N31.3633 (15)
C28—C291.397 (2)N3—H30.8600
C29—C301.377 (2)N4—N51.3551 (15)
C29—N61.409 (2)N6—H6A0.8600
C30—C311.378 (3)N7—N81.3600 (15)
C30—H300.9300N8—H8A0.8600
C31—C321.379 (3)N9—N101.3552 (15)
O1—C1—N1128.01 (14)O5—C34—C35121.83 (13)
O1—C1—C2125.91 (13)N8—C34—C35115.00 (12)
N1—C1—C2106.09 (12)N9—C35—C36112.34 (12)
N2—C2—C3125.42 (13)N9—C35—C34121.64 (12)
N2—C2—C1128.38 (12)C36—C35—C34125.93 (13)
C3—C2—C1106.20 (12)C37—C36—C35105.10 (13)
C8—C3—C4121.01 (13)C37—C36—H36127.5
C8—C3—C2132.41 (14)C35—C36—H36127.5
C4—C3—C2106.58 (12)N10—C37—C36106.26 (12)
C5—C4—C3121.34 (14)N10—C37—C38B127.9 (10)
C5—C4—N1129.02 (14)C36—C37—C38B125.7 (9)
C3—C4—N1109.64 (12)N10—C37—C38121.9 (5)
C6—C5—C4117.12 (15)C36—C37—C38131.6 (5)
C6—C5—H5121.4C39—C38—C43118.5 (4)
C4—C5—H5121.4C39—C38—C37117.3 (5)
C5—C6—C7122.18 (15)C43—C38—C37124.2 (5)
C5—C6—H6118.9C38—C39—C40121.3 (4)
C7—C6—H6118.9C38—C39—H39119.4
C6—C7—C8120.49 (16)C40—C39—H39119.4
C6—C7—H7119.8C41—C40—C39119.4 (4)
C8—C7—H7119.8C41—C40—H40120.3
C3—C8—C7117.84 (15)C39—C40—H40120.3
C3—C8—H8121.1O6—C41—C40125.1 (4)
C7—C8—H8121.1O6—C41—C42115.1 (4)
O2—C9—N3123.67 (13)C40—C41—C42119.8 (4)
O2—C9—C10121.62 (13)C43—C42—C41120.4 (4)
N3—C9—C10114.64 (12)C43—C42—H42119.8
N4—C10—C11112.24 (12)C41—C42—H42119.8
N4—C10—C9120.88 (12)C42—C43—C38120.6 (4)
C11—C10—C9126.71 (14)C42—C43—H43119.7
C12—C11—C10105.32 (13)C38—C43—H43119.7
C12—C11—H11127.3O6—C44—H44A109.5
C10—C11—H11127.3O6—C44—H44B109.5
N5—C12—C11106.04 (12)H44A—C44—H44B109.5
N5—C12—C13124.09 (13)O6—C44—H44C109.5
C11—C12—C13129.74 (14)H44A—C44—H44C109.5
C18—C13—C14118.16 (13)H44B—C44—H44C109.5
C18—C13—C12121.16 (13)C41—O6—C44117.2 (4)
C14—C13—C12120.57 (13)C39B—C38B—C43B118.4 (8)
C15—C14—C13121.15 (14)C39B—C38B—C37124.9 (10)
C15—C14—H14119.4C43B—C38B—C37116.6 (10)
C13—C14—H14119.4C38B—C39B—C40B121.6 (8)
C14—C15—C16119.92 (14)C38B—C39B—H39B119.2
C14—C15—H15120.0C40B—C39B—H39B119.2
C16—C15—H15120.0C41B—C40B—C39B119.0 (7)
O3—C16—C17124.25 (14)C41B—C40B—H40B120.5
O3—C16—C15115.98 (13)C39B—C40B—H40B120.5
C17—C16—C15119.77 (13)O6B—C41B—C40B124.6 (7)
C16—C17—C18119.86 (14)O6B—C41B—C42B115.1 (7)
C16—C17—H17120.1C40B—C41B—C42B120.3 (7)
C18—C17—H17120.1C41B—C42B—C43B119.9 (7)
C13—C18—C17121.13 (14)C41B—C42B—H42B120.1
C13—C18—H18119.4C43B—C42B—H42B120.1
C17—C18—H18119.4C38B—C43B—C42B120.7 (8)
O3—C19—H19A109.5C38B—C43B—H43B119.6
O3—C19—H19B109.5C42B—C43B—H43B119.6
H19A—C19—H19B109.5O6B—C44B—H44D109.5
O3—C19—H19C109.5O6B—C44B—H44E109.5
H19A—C19—H19C109.5H44D—C44B—H44E109.5
H19B—C19—H19C109.5O6B—C44B—H44F109.5
C16—O3—C19117.47 (13)H44D—C44B—H44F109.5
C21—C20—C25120.70 (16)H44E—C44B—H44F109.5
C21—C20—N5119.22 (15)C41B—O6B—C44B116.7 (8)
C25—C20—N5120.07 (16)C50—C45—C46121.20 (16)
C20—C21—C22119.56 (19)C50—C45—N10120.11 (15)
C20—C21—H21120.2C46—C45—N10118.69 (15)
C22—C21—H21120.2C47—C46—C45119.2 (2)
C23—C22—C21120.3 (2)C47—C46—H46120.4
C23—C22—H22119.8C45—C46—H46120.4
C21—C22—H22119.8C48—C47—C46119.9 (2)
C22—C23—C24119.96 (19)C48—C47—H47120.0
C22—C23—H23120.0C46—C47—H47120.0
C24—C23—H23120.0C49—C48—C47120.41 (19)
C23—C24—C25121.0 (2)C49—C48—H48119.8
C23—C24—H24119.5C47—C48—H48119.8
C25—C24—H24119.5C48—C49—C50120.5 (2)
C20—C25—C24118.5 (2)C48—C49—H49119.7
C20—C25—H25120.8C50—C49—H49119.7
C24—C25—H25120.8C45—C50—C49118.73 (19)
O4—C26—N6127.84 (15)C45—C50—H50120.6
O4—C26—C27125.95 (13)C49—C50—H50120.6
N6—C26—C27106.20 (12)C1—N1—C4111.48 (12)
N7—C27—C28125.61 (13)C1—N1—H1124.3
N7—C27—C26128.08 (13)C4—N1—H1124.3
C28—C27—C26106.31 (12)C2—N2—N3116.22 (12)
C33—C28—C29120.62 (14)C9—N3—N2118.68 (12)
C33—C28—C27132.60 (14)C9—N3—H3120.7
C29—C28—C27106.77 (13)N2—N3—H3120.7
C30—C29—C28121.35 (15)C10—N4—N5104.15 (11)
C30—C29—N6129.16 (15)N4—N5—C12112.22 (12)
C28—C29—N6109.49 (13)N4—N5—C20118.97 (12)
C29—C30—C31117.51 (16)C12—N5—C20128.78 (11)
C29—C30—H30121.2C26—N6—C29111.22 (13)
C31—C30—H30121.2C26—N6—H6A124.4
C30—C31—C32121.83 (15)C29—N6—H6A124.4
C30—C31—H31119.1C27—N7—N8116.77 (12)
C32—C31—H31119.1N7—N8—C34118.41 (12)
C31—C32—C33120.71 (17)N7—N8—H8A120.8
C31—C32—H32119.6C34—N8—H8A120.8
C33—C32—H32119.6C35—N9—N10104.00 (11)
C28—C33—C32117.98 (16)N9—N10—C37112.30 (11)
C28—C33—H33121.0N9—N10—C45119.87 (11)
C32—C33—H33121.0C37—N10—C45127.42 (11)
O5—C34—N8123.11 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.862.132.8594 (16)142
N3—H3···O10.862.072.7419 (17)135
N6—H6A···O20.862.132.8512 (17)142
N8—H8A···O40.862.072.7396 (16)134
C5—H5···O5i0.932.493.172 (2)130
C30—H30···O20.932.523.187 (2)129
C36—H36···O3ii0.932.443.330 (2)159
Symmetry codes: (i) x, y+1, z; (ii) x+1, −y+1/2, z−1/2.
 

Acknowledgements

We thank Cardiff University and the National Research Centre for technical support.

Funding information

Funding for this research was provided by: Researchers Supporting Project, King Saud University, Riyadh, Saudi Arabia. (award No. RSP2023R404).

References

First citationAfsah, E. M., Elmorsy, S. S., Abdelmageed, S. M. & Zaki, Z. E. (2016). Z. Naturforsch. B, 71, 1147–1157.  CrossRef Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKariuki, B. M., Abdel-Wahab, B. F., Farahat, A. A. & El-Hiti, G. A. (2022). Molbank, 2022, M1374.  CrossRef Google Scholar
 First citationKarrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y. N., Al-aizari, F. A. & Ansar, M. (2018). Molecules, 23, 134131.  CrossRef Google Scholar
 First citationKaur, M., Singh, M., Chadha, N. & Silakari, O. (2016). Eur. J. Med. Chem. 123, 858–894.  CrossRef Google Scholar
 First citationLi, X., Yu, Y. & Tu, Z. (2021). Molecules, 26, 1202.  CrossRef Google Scholar
 First citationLu, X.-Y., Wang, Z.-C., Wei, T., Yan, X.-Q., Wang, P.-F. & Zhu, H.-L. (2016). RSC Adv. 6, 22917–22935.  CrossRef Google Scholar
 First citationMacrae, 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
 First citationMohamed, H. A., Bekheit, M. S., Ewies, E. F., Awad, H. M., Betz, R., Hosten, E. C. & Abdel-Wahab, B. F. (2023). J. Mol. Struct. 1274, 134415.  CrossRef Google Scholar
 First citationQian, P., Su, J.-H., Wang, Y., Bi, M., Zha, Z. & Wang, Z. (2017). J. Org. Chem. 82, 6434–6440.  CrossRef Google Scholar
 First citationRigaku OD. (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Oxford, England.  Google Scholar
 First citationRíos, M.-C. & Portilla, J. (2022). Chemistry, 4, 940–968.  Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationWei, W.-T., Ying, W.-W., Zhu, W.-M., Wu, Y., Huang, Y.-L., Cao, Y.-Q., Wang, Y.-N. & Liang, H. (2017). Synlett, 28, 2307–2310.  CrossRef Google Scholar
 First citationYing, W.-W., Zhu, W.-M., Liang, H. & Wei, W.-T. (2018). Synlett, 29, 215–218.  Google Scholar
 First citationZi, Y., Cai, Z.-J., Wang, S.-Y. & Ji, S.-J. (2014). Org. Lett. 16, 3094–3097.  Web of Science CrossRef CAS Google Scholar
 First citationZora, M., Kivrak, A. & Yazici, C. (2011). J. Org. Chem. 76, 6726–6742.  CrossRef 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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 8| Part 5| May 2023| x230455
https://doi.org/10.1107/S2414314623004558