Synthesis and crystal structure of N-(5-acetyl-4-methyl­pyrimidin-2-yl)benzene­sulfonamide

Mohamed-Ezzat, R.A.; Kariuki, B.M.; Azzam, R.A.

doi:10.1107/S2056989023001871

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 4| April 2023| Pages 331-334

https://doi.org/10.1107/S2056989023001871

Open

access

Synthesis and crystal structure of N-(5-acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide

Reham A. Mohamed-Ezzat,^a Benson M. Kariuki ^b and Rasha A. Azzam ^c ^*

^aChemistry of Natural & Microbial Products Department, National Research Center, Cairo, Egypt, ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10, 3AT, United Kingdom, and ^cDepartment of Chemistry, Helwan University, Cairo, Egypt
^*Correspondence e-mail: rashaazzam8@gmail.com

Edited by C. Schulzke, Universität Greifswald, Germany (Received 7 February 2023; accepted 28 February 2023; online 15 March 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.

N-(5-Acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide, C₁₃H₁₃N₃O₃S, was sythesized and characterized by single-crystal X-ray diffraction. In the crystal, π–π interactions between the phenyl and pyrimidine groups of neighbouring molecules form molecular chains parallel to [010]. Adjacent molecular chains are linked by N—H⋯N hydrogen-bonding interactions between the pyrimidine and amine groups of neighbouring molecules, resulting in a three-dimensional network.

Keywords: synthesis; pyrimidine sulfonamide; crystal structure; X-ray diffraction.

CCDC reference: 2245275

1. Chemical context

Sulfonamide-bearing molecules with one or several pharmacological scaffolds constitute a class of drugs with antiviral, anticancer, anti-carbonic anhydrase (CA), diuretic, cyclooxigenase 2 (COX2) inhibitory, protease inhibitory, and/or antibacterial activities (Supuran, 2003 ; Scozzafava et al., 2003 ; Casini & Scozzafava, 2002 ). It is noteworthy that the sulfonamide moiety is one of the significant, privileged building blocks that medicinal chemists frequently find in potent drugs (Elgemeie et al., 2019 ). Thus, many widely marketed drugs incorporate this moiety. Several pyrimidine sulfonamides and other pyrimidine analogues that could be incorporated in new designs for bioactive molecules with medicinal applications have already been considered (Azzam, 2019 ; Azzam & Elgemeie, 2019 ; Azzam et al., 2017 , 2019 ; Mohamed-Ezzat et al., 2021 , 2022 ; Elgemeie et al., 2015a ,b , 2017 ). The synthesis of N-(5-acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide (AMBS) was reported several decades ago (Gutsche et al., 1964 ). In this article, we describe an alternative novel one-pot reaction methodology for the synthesis of this compound, which was also crystallized and crystallographically investigated.

2. Structural commentary

N-(5-Acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide (AMBS) crystallizes in the monoclinic system, space group P2₁/c and contains four molecules in the unit cell (Z = 4). The asymmetric unit is shown in Fig. 1. The acetaldehyde group of the molecule is disordered with two components related by a twist of 31.3 (1)° about the C_ar—C bond. Apart from a slight twist of the aldehyde group associated with the disorder, the 1-(2-amino-4-methylpyrimidin-5-yl)ethan-1-one segment of the molecule is essentially planar, the sulfonamide atom S1 being located only 0.423 (1) Å away from the plane of the pyrimidine group. The molecule exhibits a C7—N1—S1—C1 torsion angle of −79.0 (2)°, while the twist between the planes of the phenyl group and the pyrimidine ring comprises a dihedral angle of 63.07 (7)°.

Figure 1
The molecular structure of the title compound with atom labels and 50% probability atomic displacement ellipsoids.

3. Supramolecular features

The packing of AMBS is shown in Fig. 2. In the crystal, partial π–π overlap is observed between the phenyl group of one molecule and the pyrimidine group of an adjacent one related by 2₁ symmetry (1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z or 1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z). The dihedral angle between the planes of the rings is 9.04 (10)° with a ring centroid-to-centroid distance of 3.769 (1) Å (Fig. 3). The slippage distances between the overlapping rings are 1.44 Å (1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z) and 1.58 Å (1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z). These π–π interactions form chains in the structure in which one AMBS molecule comprises the linker between two further molecules. The bent nature of the molecule results in a zigzag pattern of chains propagating parallel to [010].

Figure 2
Crystal packing viewed down the a axis with N—H⋯N hydrogen bonds shown as dotted lines.

Figure 3
A segment of the crystal structure showing a chain of molecules linked by π–π interactions. The dotted lines connect the centroids of the molecules involved.

The hydrogen-bonding interactions in the crystal are summarized in Table 1. Two linear N—H⋯N hydrogen bonds, with N⋯N distances of 2.891 (2) Å, occur between two neighbouring molecules related by inversion symmetry (1 − x, 1 − y, 1 − z). A pair of hydrogen bonds is formed between the pyrimidine and amine groups of the two molecules, resulting in a R₂²(8) geometry (Fig. 2). The hydrogen bonds link the molecular chains formed by the π–π interactions and are perpendicular to the chains' protrusion. Additionally, non-classical hydrogen-bonding contacts of the C—H⋯O type with C⋯O distances in the range of ca 2.7–3.4 Å help to consolidate the structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.83 (2)	2.06 (2)	2.891 (2)	179 (2)
C6—H6⋯O2ⁱⁱ	0.93	2.62	3.338 (3)	135
C10—H10⋯O1ⁱ	0.93	2.54	3.243 (3)	133
C11—H11B⋯O3A	0.96	2.26	2.769 (7)	113
C13A—H13E⋯O1ⁱⁱⁱ	0.96	2.50	3.40 (3)	156
Symmetry codes: (i) ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

4. Database survey

A survey of the Cambridge Structural Database (Groom et al., 2016 ; accessed February 2023) using CONQUEST (Bruno et al., 2002 ) for structures containing the N-(pyrimidin-2-yl)benzenesulfonamide group gave 164 hits, i.e. too many for them all to be analysed in detail.

An example of a closely related compound is 4,5,6-trimethyl-2-[(phenylsulfonyl)amino]pyrimidine (TPAP) (refcode VENKIJ; Li & Yang, 2006 ). In this structure, the dihedral angle between the planes through the phenyl and pyrimidine rings is 91.9°, larger than that observed for the title compound AMBS [63.07 (7)°]. In contrast to AMBS, π–π interactions are only observed between the pyrimidine rings in TPAP, resulting in stacking along the a-axis with interplanar distances of 3.81 Å.

Another closely related compound is N-(pyrimidin-2-yl)benzenesulfonamide (PBS) (refcode XIFKAZ01; Coles et al., 2000 ). In PBS, the dihedral angle between the planes through the phenyl and pyrimidine rings is 74.5°, again larger than for AMBS. Also unlike in AMBS, π–π interactions occur in PBS between pairs of molecules involving only the pyrimidine rings and with an interplanar distance of 3.5 Å. Similarly to AMBS, two linear N—H⋯N hydrogen bonds are observed in PBS between the pyrimidine and amine groups of neighbouring molecules, resulting in similar R₂²(8) motifs.

5. Synthesis and crystallization

Phenylsulfonyl guanidine 1 is a common starting material for the synthesis of several heterocyclic compounds and has been utilized effectively in the generation of a range of biologically active compounds. Our approach was based on synthesizing the substituted sulfonyl derivative 4 by reacting the sulfonyl guanidine 1 with triethylorthoformate 2 and acetyl acetone 3 (Fig. 4). The target product was identified by NMR spectroscopy and X-ray crystallography.

Figure 4
The synthesis of the title compound (4). Reagents & Conditions: (i) reflux; 6 h.

Synthesis of compound 4: Triethylorthoformate (5 ml) was added to a mixture of phenylsulfonyl guanidine (0.05 mol) and acetyl acetone (0.1 mol). The reaction mixture was then refluxed for 6 h. After cooling, the resulting precipitate was filtered and crystallized from ethanol.

Orange crystals; yield 45%; m.p. 469 K. ¹H NMR (400 MHz, DMSO-d₆): δ 2.49 (s, 3H, CH₃), 2.52 (s, 3H, CH₃), 7.57–7.66 (m, 3H, Ar-H), 8.00–8.02 (m, 2H, Ar-H), 8.93 (s, 1H, CH-pyrimidine), 12.34 (s, 1H, NH). Analysis calculated for C₁₃H₁₃N₃O₃S (291.33): C, 53.60; H, 4.50; N, 14.42; S, 11.01. Found: C, 53.60; H, 4.49; N, 14.41; S, 11.00.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N—H hydrogen was refined freely. The remaining hydrogen atoms were positioned geometrically and using a riding model [C—H = 0.93–0.96 Å with U_iso(H) = 1.2 or 1.5 U_eq(C). The acetaldehyde group of the molecule is disordered with two components related by a twist of 31.3 (1)° about the C_ar—C bond. In the refinement, the two components were restrained to have similar geometry (SAME in SHELXL) and atomic displacement parameters (SIMU and ISOR). The occupancies of the two components refined to 0.591 (11)/0.409 (11).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₃N₃O₃S
M_r	291.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.0699 (6), 14.7429 (6), 10.5212 (7)
β (°)	113.900 (7)
V (Å³)	1428.04 (16)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.44 × 0.24 × 0.16

Data collection
Diffractometer	Rigaku SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.484, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12642, 3532, 2548
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.07
No. of reflections	3532
No. of parameters	216
No. of restraints	84
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/1 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Supporting information

CCDC reference: 2245275

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023001871/yz2029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023001871/yz2029Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023001871/yz2029Isup3.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: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020), ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2020).

N-(5-Acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide top

Crystal data top

C₁₃H₁₃N₃O₃S	F(000) = 608
M_r = 291.32	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0699 (6) Å	Cell parameters from 5035 reflections
b = 14.7429 (6) Å	θ = 3.9–27.7°
c = 10.5212 (7) Å	µ = 0.24 mm⁻¹
β = 113.900 (7)°	T = 293 K
V = 1428.04 (16) Å³	Block, orange
Z = 4	0.44 × 0.24 × 0.16 mm

Data collection top

Rigaku SuperNova, Dual, Cu at home/near, Atlas diffractometer	2548 reflections with I > 2σ(I)
ω scans	R_int = 0.026
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	θ_max = 29.5°, θ_min = 3.5°
T_min = 0.484, T_max = 1.000	h = −13→10
12642 measured reflections	k = −18→18
3532 independent reflections	l = −13→14

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0493P)² + 0.420P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3532 reflections	Δρ_max = 0.23 e Å⁻³
216 parameters	Δρ_min = −0.29 e Å⁻³
84 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5229 (2)	0.75192 (12)	0.26887 (19)	0.0461 (4)
C2	0.6205 (2)	0.76291 (14)	0.2086 (2)	0.0552 (5)
H2	0.630570	0.718727	0.150041	0.066*
C3	0.7033 (2)	0.84155 (15)	0.2374 (3)	0.0651 (6)
H3	0.768869	0.850929	0.196825	0.078*
C4	0.6886 (3)	0.90550 (15)	0.3257 (3)	0.0712 (7)
H4	0.746248	0.957279	0.346473	0.085*
C5	0.5901 (3)	0.89393 (15)	0.3833 (2)	0.0696 (6)
H5	0.579890	0.938259	0.441639	0.083*
C6	0.5065 (3)	0.81732 (14)	0.3555 (2)	0.0580 (5)
H6	0.439261	0.809307	0.394462	0.070*
C7	0.6186 (2)	0.52796 (12)	0.37144 (19)	0.0463 (4)
C8	0.8002 (2)	0.49089 (16)	0.3045 (2)	0.0579 (5)
C10	0.7564 (2)	0.40722 (14)	0.4752 (2)	0.0568 (5)
H10	0.780068	0.359996	0.539203	0.068*
C11	0.8767 (3)	0.5141 (2)	0.2123 (3)	0.0835 (8)
H11A	0.853870	0.469409	0.140165	0.125*
H11B	0.979663	0.514976	0.266457	0.125*
H11C	0.845364	0.572710	0.171410	0.125*
N1	0.50291 (19)	0.58192 (11)	0.35938 (18)	0.0508 (4)
N2	0.69070 (18)	0.54638 (11)	0.29291 (17)	0.0537 (4)
N3	0.64728 (17)	0.46152 (10)	0.46533 (16)	0.0496 (4)
O1	0.28821 (16)	0.67414 (10)	0.25840 (16)	0.0653 (4)
O2	0.39885 (17)	0.61859 (10)	0.10316 (14)	0.0621 (4)
S1	0.41467 (5)	0.65419 (3)	0.23421 (5)	0.04929 (17)
C9	0.8367 (2)	0.41647 (16)	0.3968 (2)	0.0600 (5)	0.591 (11)
C12	0.9420 (7)	0.3432 (4)	0.3990 (8)	0.0750 (19)	0.591 (11)
C13	0.9860 (17)	0.2756 (10)	0.5150 (18)	0.098 (4)	0.591 (11)
H13A	1.053800	0.233375	0.505298	0.148*	0.591 (11)
H13B	0.901665	0.243536	0.511702	0.148*	0.591 (11)
H13C	1.030623	0.306600	0.602434	0.148*	0.591 (11)
O3	0.9931 (8)	0.3397 (4)	0.3128 (8)	0.110 (2)	0.591 (11)
C9A	0.8367 (2)	0.41647 (16)	0.3968 (2)	0.0600 (5)	0.409 (11)
C12A	0.9727 (9)	0.3620 (7)	0.4306 (12)	0.079 (3)	0.409 (11)
C13A	0.990 (2)	0.2750 (12)	0.509 (3)	0.089 (4)	0.409 (11)
H13D	1.082486	0.248722	0.525215	0.133*	0.409 (11)
H13E	0.913988	0.233796	0.454891	0.133*	0.409 (11)
H13F	0.983594	0.286757	0.595831	0.133*	0.409 (11)
O3A	1.0616 (8)	0.3857 (7)	0.3876 (10)	0.106 (3)	0.409 (11)
H1	0.458 (2)	0.5700 (14)	0.409 (2)	0.054 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0557 (11)	0.0456 (9)	0.0403 (10)	0.0056 (8)	0.0228 (9)	0.0082 (7)
C2	0.0619 (13)	0.0559 (11)	0.0551 (12)	0.0062 (9)	0.0311 (10)	0.0070 (9)
C3	0.0567 (13)	0.0676 (14)	0.0760 (16)	0.0015 (10)	0.0320 (12)	0.0183 (11)
C4	0.0695 (15)	0.0511 (12)	0.0789 (17)	−0.0026 (10)	0.0157 (13)	0.0080 (11)
C5	0.0897 (18)	0.0535 (12)	0.0634 (14)	0.0051 (11)	0.0287 (13)	−0.0043 (10)
C6	0.0754 (15)	0.0552 (11)	0.0510 (12)	0.0089 (10)	0.0335 (11)	0.0040 (9)
C7	0.0469 (11)	0.0518 (10)	0.0433 (10)	0.0003 (8)	0.0215 (9)	0.0043 (7)
C8	0.0491 (12)	0.0804 (14)	0.0498 (12)	−0.0014 (10)	0.0258 (10)	0.0012 (10)
C10	0.0515 (12)	0.0632 (12)	0.0570 (12)	0.0109 (9)	0.0233 (10)	0.0133 (9)
C11	0.0691 (16)	0.125 (2)	0.0738 (17)	0.0090 (15)	0.0472 (14)	0.0168 (15)
N1	0.0595 (10)	0.0514 (9)	0.0521 (10)	0.0093 (7)	0.0336 (8)	0.0141 (7)
N2	0.0550 (10)	0.0635 (10)	0.0499 (10)	−0.0001 (8)	0.0289 (8)	0.0072 (7)
N3	0.0506 (9)	0.0558 (9)	0.0481 (9)	0.0081 (7)	0.0259 (8)	0.0112 (7)
O1	0.0542 (9)	0.0753 (9)	0.0733 (10)	0.0134 (7)	0.0331 (8)	0.0233 (8)
O2	0.0792 (11)	0.0595 (8)	0.0457 (8)	−0.0060 (7)	0.0234 (7)	0.0020 (6)
S1	0.0546 (3)	0.0506 (3)	0.0465 (3)	0.0042 (2)	0.0244 (2)	0.00978 (19)
C9	0.0466 (11)	0.0798 (14)	0.0577 (13)	0.0102 (10)	0.0254 (10)	0.0069 (10)
C12	0.045 (2)	0.101 (3)	0.084 (4)	0.011 (2)	0.030 (3)	0.006 (3)
C13	0.081 (6)	0.098 (5)	0.094 (6)	0.048 (5)	0.012 (5)	0.016 (5)
O3	0.096 (4)	0.128 (4)	0.144 (5)	0.037 (3)	0.087 (4)	0.017 (3)
C9A	0.0466 (11)	0.0798 (14)	0.0577 (13)	0.0102 (10)	0.0254 (10)	0.0069 (10)
C12A	0.054 (4)	0.105 (4)	0.077 (4)	0.025 (4)	0.025 (4)	0.001 (4)
C13A	0.072 (7)	0.107 (8)	0.086 (7)	0.025 (7)	0.032 (6)	−0.007 (7)
O3A	0.070 (4)	0.144 (6)	0.127 (6)	0.026 (4)	0.062 (4)	0.009 (4)

Geometric parameters (Å, º) top

C1—C2	1.378 (3)	C10—C9	1.376 (3)
C1—C6	1.382 (3)	C10—H10	0.9300
C1—S1	1.7538 (19)	C11—H11A	0.9600
C2—C3	1.388 (3)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.373 (3)	N1—S1	1.6465 (16)
C3—H3	0.9300	N1—H1	0.83 (2)
C4—C5	1.367 (3)	O1—S1	1.4267 (15)
C4—H4	0.9300	O2—S1	1.4226 (15)
C5—C6	1.368 (3)	C9—C12	1.507 (4)
C5—H5	0.9300	C12—O3	1.211 (5)
C6—H6	0.9300	C12—C13	1.497 (6)
C7—N2	1.330 (2)	C13—H13A	0.9600
C7—N3	1.337 (2)	C13—H13B	0.9600
C7—N1	1.374 (2)	C13—H13C	0.9600
C8—N2	1.338 (3)	C9A—C12A	1.501 (5)
C8—C9A	1.412 (3)	C12A—O3A	1.207 (5)
C8—C9	1.412 (3)	C12A—C13A	1.495 (6)
C8—C11	1.502 (3)	C13A—H13D	0.9600
C10—N3	1.329 (2)	C13A—H13E	0.9600
C10—C9A	1.376 (3)	C13A—H13F	0.9600

C2—C1—C6	121.33 (19)	C7—N1—S1	127.69 (14)
C2—C1—S1	120.01 (15)	C7—N1—H1	118.2 (14)
C6—C1—S1	118.66 (15)	S1—N1—H1	112.6 (15)
C1—C2—C3	118.4 (2)	C7—N2—C8	117.10 (17)
C1—C2—H2	120.8	C10—N3—C7	115.02 (17)
C3—C2—H2	120.8	O2—S1—O1	119.43 (10)
C4—C3—C2	120.1 (2)	O2—S1—N1	110.41 (9)
C4—C3—H3	120.0	O1—S1—N1	102.84 (9)
C2—C3—H3	120.0	O2—S1—C1	108.71 (9)
C5—C4—C3	120.8 (2)	O1—S1—C1	108.55 (9)
C5—C4—H4	119.6	N1—S1—C1	106.06 (9)
C3—C4—H4	119.6	C10—C9—C8	115.92 (19)
C4—C5—C6	120.2 (2)	C10—C9—C12	120.0 (3)
C4—C5—H5	119.9	C8—C9—C12	123.6 (3)
C6—C5—H5	119.9	O3—C12—C13	120.4 (5)
C5—C6—C1	119.3 (2)	O3—C12—C9	121.9 (4)
C5—C6—H6	120.3	C13—C12—C9	117.6 (5)
C1—C6—H6	120.3	C12—C13—H13A	109.5
N2—C7—N3	126.86 (17)	C12—C13—H13B	109.5
N2—C7—N1	118.71 (17)	H13A—C13—H13B	109.5
N3—C7—N1	114.43 (16)	C12—C13—H13C	109.5
N2—C8—C9A	120.86 (18)	H13A—C13—H13C	109.5
N2—C8—C9	120.86 (18)	H13B—C13—H13C	109.5
N2—C8—C11	114.9 (2)	C10—C9A—C8	115.92 (19)
C9A—C8—C11	124.2 (2)	C10—C9A—C12A	120.4 (3)
C9—C8—C11	124.2 (2)	C8—C9A—C12A	122.5 (3)
N3—C10—C9A	124.15 (19)	O3A—C12A—C13A	121.1 (5)
N3—C10—C9	124.15 (19)	O3A—C12A—C9A	120.1 (5)
N3—C10—H10	117.9	C13A—C12A—C9A	118.6 (6)
C9—C10—H10	117.9	C12A—C13A—H13D	109.5
C8—C11—H11A	109.5	C12A—C13A—H13E	109.5
C8—C11—H11B	109.5	H13D—C13A—H13E	109.5
H11A—C11—H11B	109.5	C12A—C13A—H13F	109.5
C8—C11—H11C	109.5	H13D—C13A—H13F	109.5
H11A—C11—H11C	109.5	H13E—C13A—H13F	109.5
H11B—C11—H11C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.83 (2)	2.06 (2)	2.891 (2)	179 (2)
C6—H6···O2ⁱⁱ	0.93	2.62	3.338 (3)	135
C10—H10···O1ⁱ	0.93	2.54	3.243 (3)	133
C11—H11B···O3A	0.96	2.26	2.769 (7)	113
C13A—H13E···O1ⁱⁱⁱ	0.96	2.50	3.40 (3)	156

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Funding information

We thank Helwan University for funding this research.

References

Azzam, R. A. (2019). J. Heterocycl. Chem. 56, 619–627. Web of Science CrossRef CAS Google Scholar
Azzam, R. A. & Elgemeie, G. H. (2019). Med. Chem. Res. 28, 62–70. Web of Science CrossRef CAS Google Scholar
Azzam, R. A., Elgemeie, G. H., Elsayed, R. E. & Jones, P. G. (2017). Acta Cryst. E73, 1041–1043. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Elgemeie, G. H., Osman, R. R. & Jones, P. G. (2019). Acta Cryst. E75, 367–371. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389–397. Web of Science CrossRef CAS IUCr Journals Google Scholar
Casini, A. & Scozzafava, A. (2002). Expert Opin. Ther. Pat. 12, 1307–1327. Web of Science CrossRef CAS Google Scholar
Coles, S. J., Hursthouse, M. B., Mayer, T. A. & Threlfall, T. L. (2000). University of Southampton, Crystal Structure Report Archive, 188. Google Scholar
Elgemeie, G. H., Azzam, R. A. & Elsayed, R. E. (2019). Med. Chem. Res. 28, 1099–1131. Web of Science CrossRef CAS Google Scholar
Elgemeie, G. H., Mohamed, R. A., Hussein, H. A. & Jones, P. G. (2015a). Acta Cryst. E71, 1322–1324. CSD CrossRef IUCr Journals Google Scholar
Elgemeie, G. H., Salah, A. M., Abbas, N. S., Hussein, H. A. & Mohamed, R. A. (2017). Nucleosides Nucleotides Nucleic Acids, 36, 213–223. Web of Science CrossRef CAS PubMed Google Scholar
Elgemeie, G. H., Salah, A. M., Mohamed, R. A. & Jones, P. G. (2015b). Acta Cryst. E71, 1319–1321. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals 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
Gutsche, K., Harwart, A., Horstmann, H., Priewe, H., Raspe, G., Schraufstaetter, E., Wirtz, S. & Woerffel, U. (1964). Arzneim.-Forsch. 14, 373–376. CAS Google Scholar
Li, G.-C. & Yang, F.-L. (2006). Acta Cryst. E62, o4154–o4155. Web of Science CSD CrossRef IUCr Journals 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
Mohamed-Ezzat, R. A., Elgemeie, G. H. & Jones, P. G. (2021). Acta Cryst. E77, 547–550. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mohamed-Ezzat, R. A., Kariuki, B. M. & Azzam, R. A. (2022). IUCrData, 7, x221033. Google Scholar
Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Scozzafava, A., Owa, T., Mastrolorenzo, A. & Supuran, C. T. (2003). Curr. Med. Chem. 10, 925–953. Web of Science CrossRef PubMed CAS 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
Supuran, C. T. (2003). Expert Opin. Investig. Drugs, 12, 283–287. CrossRef PubMed CAS 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.