(E)-2-Benzoyl-3-[1-phenyl-3-(thio­phen-2-yl)-1H-pyrazol-4-yl]acrylo­nitrile

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314618001712

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x180171

https://doi.org/10.1107/S2414314618001712

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(E)-2-Benzoyl-3-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]acrylonitrile

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e ‡

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and ^eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by H. Ishida, Okayama University, Japan (Received 23 December 2017; accepted 29 January 2018; online 31 January 2018)

The asymmetric unit of the title compound, C₂₃H₁₅N₃OS, consists of two crystallographically independent molecules, which are related by a pseudo-inversion centre. In one molecule, the pyrazolyl ring makes dihedral angles of 35.7 (4), 19.1 (1) and 47.3 (1)°, respectively, with the thiophenyl ring, the attached phenyl ring and the phenyl ring of the benzoyl group. In the second molecule, the corresponding values are 37.4 (1), 16.1 (1) and 48.2 (1)°, respectively. In the crystal, the two independent molecules are linked to each other via a π–π interaction between the pyrazolyl rings [centroid–centroid distance = 3.578 (12) Å]. Weak intermolecular C—H⋯O interactions are also observed. The thiophenyl ring of one molecule is disordered over two orientations, with a refined occupancy ratio of 0.768 (3):0.232 (3).

Keywords: crystal structure; heterocycles; π–π interaction.

CCDC reference: 1820339

Structure description

3-(2′-Thienyl)pyrazole-based heterocycles show various biological applications with antimicrobial, antioxidant, anti-inflammatory and analgesic activities (Abdel-Wahab et al., 2011 , 2012 ; Naim et al., 2016 ). Various synthetic approaches have been reported for the formation of heterocycles containing thiophene and pyrazole moieties (Abdel-Wahab et al., 2010 ; Bratenko et al., 2005 ).

The asymmetric unit consists of two unique molecules, which are related to each other by a pseudo-inversion centre (Fig. 1). The N1/N2/C7–C9 pyrazolyl ring makes dihedral angles of 35.7 (4), 19.1 (1) and 47.3 (1)°, respectively, with the S1/C10–C13 thiophenyl ring, the C1–C6 and C18–C23 phenyl rings, while the N4/N5/C30–C32 pyrazolyl ring makes dihedral angles of 37.4 (1), 16.1 (1) and 48.2 (1)°, respectively, with the S2/C33–C36, C24–C29 and C41–C46 rings.

Figure 1
The asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level.

In the crystal, the two independent molecules are linked through a π–π interaction between the pyrazolyl rings with a centroid–centroid distance of 3.578 (12) Å (Fig. 2). Weak intermolecular C—H⋯O hydrogen bonds (Table 1) are also observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C34—H34⋯O2ⁱ	0.93	2.61	3.396 (3)	143
C46—H46⋯O2ⁱ	0.93	2.45	3.363 (3)	167
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A packing diagram viewed along the b axis. π–π interactions are shown as dotted lines.

Synthesis and crystallization

The title compound was synthesized from reaction of a mixture of 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde and 3-oxo-3-phenylpropanenitrile in dry ethanol containing piperidine as a catalyst. The solution was refluxed for 5 h. The solid obtained was filtrated and dried. Yellow in CIF single crystals suitable for X-ray diffraction were obtained from an ethanol solution [yield 79%, m.p. 182–184°C; reported m.p. 182–184°C (Abdel-Wahab et al., 2017 )].

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The thiophenyl ring (S1/C10–C13) of one molecule is disordered over two orientations around the C7—C10 bond. The occupancies refined to 0.768 (3) and 0.232 (3). Both major and minor components were restrained to have similar geometries and the anisotropic displacement parameters of C atoms of the minor component were constrained to be the same as those of the major component.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₅N₃OS
M_r	381.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	19.2666 (10), 9.7769 (4), 20.3265 (12)
β (°)	94.423 (5)
V (Å³)	3817.5 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.19
Crystal size (mm)	0.28 × 0.15 × 0.06

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Numerical (CrysAlis PRO; Rigaku Oxford Diffraction, 2015 $[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.563, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	22054, 9267, 4750
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.167, 1.02
No. of reflections	9267
No. of parameters	524
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.30
Computer programs: CrysAlis PRO (Rigaku Oxford Diffraction, 2015 $[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ) and ORTEP-3 for Windows and WinGX (Farrugia, 2012 ).

Structural data

CCDC reference: 1820339

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618001712/is4023sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618001712/is4023Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618001712/is4023Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

(E)-2-Benzoyl-3-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]acrylonitrile top

Crystal data top

C₂₃H₁₅N₃OS	F(000) = 1584
M_r = 381.44	D_x = 1.327 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 19.2666 (10) Å	Cell parameters from 4056 reflections
b = 9.7769 (4) Å	θ = 3.5–26.2°
c = 20.3265 (12) Å	µ = 0.19 mm⁻¹
β = 94.423 (5)°	T = 296 K
V = 3817.5 (3) Å³	Plate, yellow
Z = 8	0.28 × 0.15 × 0.06 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	4750 reflections with I > 2σ(I)
ω scans	R_int = 0.038
Absorption correction: numerical (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	θ_max = 29.9°, θ_min = 2.9°
T_min = 0.563, T_max = 0.990	h = −19→26
22054 measured reflections	k = −12→13
9267 independent reflections	l = −26→26

Refinement top

Refinement on F²	30 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0637P)² + 0.3861P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
9267 reflections	Δρ_max = 0.16 e Å⁻³
524 parameters	Δρ_min = −0.30 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	−0.01004 (11)	−0.0978 (2)	0.14670 (12)	0.0454 (5)
C2	−0.00943 (13)	−0.2356 (2)	0.16190 (14)	0.0609 (7)
H2	−0.031422	−0.267522	0.198053	0.073*
C3	0.02426 (14)	−0.3250 (3)	0.12271 (15)	0.0695 (8)
H3	0.024800	−0.417852	0.132607	0.083*
C4	0.05675 (14)	−0.2795 (3)	0.06974 (14)	0.0650 (7)
H4	0.079374	−0.340837	0.043723	0.078*
C5	0.05588 (13)	−0.1424 (3)	0.05496 (13)	0.0626 (7)
H5	0.077931	−0.111057	0.018732	0.075*
C6	0.02243 (12)	−0.0504 (2)	0.09361 (12)	0.0551 (6)
H6	0.022041	0.042453	0.083616	0.066*
C7	−0.08758 (11)	0.0626 (2)	0.27623 (12)	0.0449 (5)
C8	−0.09450 (11)	0.1731 (2)	0.23004 (11)	0.0441 (5)
C9	−0.06568 (11)	0.1226 (2)	0.17469 (12)	0.0465 (5)
H9	−0.061972	0.169013	0.135190	0.056*
C10	−0.10581 (12)	0.0561 (2)	0.34403 (12)	0.0481 (6)	0.768 (3)
C11	−0.1596 (6)	0.1225 (13)	0.3717 (5)	0.062 (3)	0.768 (3)
H11	−0.191951	0.178354	0.348419	0.075*	0.768 (3)
C12	−0.1591 (3)	0.0939 (6)	0.4414 (3)	0.0722 (15)	0.768 (3)
H12	−0.192933	0.124859	0.468043	0.087*	0.768 (3)
C13	−0.1036 (3)	0.0167 (6)	0.4635 (2)	0.0678 (14)	0.768 (3)
H13	−0.093513	−0.007245	0.507529	0.081*	0.768 (3)
S1	−0.05506 (10)	−0.03086 (17)	0.40164 (7)	0.0597 (4)	0.768 (3)
C10A	−0.10581 (12)	0.0561 (2)	0.34403 (12)	0.0481 (6)	0.232 (3)
C11A	−0.0610 (12)	−0.009 (3)	0.3929 (9)	0.062 (3)	0.232 (3)
H11A	−0.018667	−0.049121	0.384726	0.075*	0.232 (3)
C12A	−0.0885 (13)	−0.007 (3)	0.4559 (9)	0.0722 (15)	0.232 (3)
H12A	−0.068910	−0.051770	0.493105	0.087*	0.232 (3)
C13A	−0.1462 (13)	0.070 (3)	0.4546 (9)	0.0678 (14)	0.232 (3)
H13A	−0.169438	0.091173	0.491652	0.081*	0.232 (3)
S1A	−0.1719 (7)	0.1219 (13)	0.3767 (6)	0.078 (3)	0.232 (3)
C14	−0.12398 (11)	0.3051 (2)	0.24226 (12)	0.0470 (5)
H14	−0.133136	0.322213	0.285753	0.056*
C15	−0.14026 (11)	0.4081 (2)	0.19891 (12)	0.0481 (6)
C16	−0.12709 (14)	0.3971 (2)	0.13089 (16)	0.0611 (7)
C17	−0.16859 (12)	0.5420 (2)	0.21806 (13)	0.0516 (6)
C18	−0.20071 (12)	0.5570 (2)	0.28148 (12)	0.0513 (6)
C19	−0.18888 (14)	0.6776 (2)	0.31687 (14)	0.0632 (7)
H19	−0.160196	0.744603	0.301042	0.076*
C20	−0.21904 (16)	0.6985 (3)	0.37465 (16)	0.0778 (9)
H20	−0.210875	0.779466	0.397992	0.093*
C21	−0.26172 (16)	0.5994 (3)	0.39848 (15)	0.0788 (9)
H21	−0.281367	0.612784	0.438361	0.095*
C22	−0.27520 (14)	0.4806 (3)	0.36313 (15)	0.0681 (7)
H22	−0.304895	0.415018	0.378622	0.082*
C23	−0.24482 (12)	0.4590 (2)	0.30512 (13)	0.0550 (6)
H23	−0.253778	0.378644	0.281531	0.066*
C24	0.03423 (11)	0.3885 (2)	0.31778 (13)	0.0498 (6)
C25	0.03157 (13)	0.5267 (2)	0.30351 (15)	0.0671 (8)
H25	0.051478	0.560383	0.266545	0.081*
C26	−0.00072 (16)	0.6135 (3)	0.34441 (18)	0.0842 (9)
H26	−0.002661	0.706520	0.334874	0.101*
C27	−0.03021 (15)	0.5654 (3)	0.39917 (17)	0.0810 (9)
H27	−0.052164	0.625314	0.426430	0.097*
C28	−0.02707 (14)	0.4271 (3)	0.41355 (15)	0.0735 (8)
H28	−0.046752	0.393605	0.450686	0.088*
C29	0.00541 (13)	0.3389 (3)	0.37257 (14)	0.0624 (7)
H29	0.007715	0.245937	0.382144	0.075*
C30	0.11350 (11)	0.2360 (2)	0.18758 (12)	0.0464 (6)
C31	0.12010 (11)	0.1233 (2)	0.23240 (11)	0.0436 (5)
C32	0.09022 (11)	0.1702 (2)	0.28749 (12)	0.0487 (6)
H32	0.086479	0.121975	0.326511	0.058*
C33	0.13532 (12)	0.2442 (2)	0.12074 (12)	0.0505 (6)
C34	0.19299 (13)	0.1889 (2)	0.09487 (13)	0.0572 (6)
H34	0.227400	0.140826	0.119763	0.069*
C35	0.19433 (15)	0.2129 (3)	0.02682 (14)	0.0685 (7)
H35	0.229768	0.182593	0.001853	0.082*
C36	0.13861 (17)	0.2847 (3)	0.00160 (14)	0.0760 (8)
H36	0.131071	0.308578	−0.042657	0.091*
C37	0.15047 (11)	−0.0068 (2)	0.21921 (12)	0.0468 (6)
H37	0.163354	−0.018387	0.176400	0.056*
C38	0.16320 (11)	−0.1154 (2)	0.25979 (12)	0.0473 (6)
C39	0.14342 (13)	−0.1151 (2)	0.32593 (15)	0.0560 (6)
C40	0.19362 (12)	−0.2461 (2)	0.23808 (13)	0.0528 (6)
C41	0.22781 (12)	−0.2530 (2)	0.17564 (13)	0.0537 (6)
C42	0.21698 (15)	−0.3699 (3)	0.13695 (17)	0.0753 (9)
H42	0.189011	−0.440018	0.150910	0.090*
C43	0.2470 (2)	−0.3818 (4)	0.0791 (2)	0.1062 (13)
H43	0.239296	−0.459619	0.053271	0.127*
C44	0.2886 (2)	−0.2794 (5)	0.05866 (17)	0.1052 (13)
H44	0.308100	−0.287526	0.018394	0.126*
C45	0.30226 (16)	−0.1632 (4)	0.09698 (17)	0.0849 (9)
H45	0.331730	−0.095273	0.083306	0.102*
C46	0.27149 (13)	−0.1507 (3)	0.15529 (14)	0.0600 (7)
H46	0.279869	−0.073400	0.181363	0.072*
N1	−0.04409 (9)	−0.00525 (17)	0.18823 (9)	0.0455 (5)
N2	−0.05719 (9)	−0.04497 (17)	0.25023 (10)	0.0480 (5)
N3	−0.11748 (15)	0.3875 (2)	0.07645 (14)	0.0903 (8)
N4	0.06743 (9)	0.29801 (17)	0.27477 (10)	0.0487 (5)
N5	0.08151 (10)	0.34125 (18)	0.21337 (10)	0.0502 (5)
N6	0.12700 (14)	−0.1138 (2)	0.37868 (14)	0.0815 (7)
O1	−0.16545 (9)	0.63946 (16)	0.18061 (10)	0.0706 (5)
O2	0.18950 (10)	−0.34754 (16)	0.27296 (10)	0.0746 (6)
S2	0.08406 (4)	0.32604 (7)	0.05995 (4)	0.0704 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0443 (12)	0.0460 (12)	0.0456 (15)	0.0044 (10)	0.0016 (11)	−0.0034 (11)
C2	0.0680 (15)	0.0494 (13)	0.0676 (19)	0.0063 (12)	0.0199 (14)	0.0019 (12)
C3	0.0821 (18)	0.0518 (14)	0.077 (2)	0.0158 (13)	0.0192 (16)	0.0000 (14)
C4	0.0691 (16)	0.0690 (17)	0.0569 (19)	0.0221 (14)	0.0055 (14)	−0.0082 (14)
C5	0.0638 (15)	0.0795 (18)	0.0451 (16)	0.0082 (14)	0.0082 (13)	0.0000 (13)
C6	0.0657 (15)	0.0531 (13)	0.0462 (16)	0.0023 (12)	0.0019 (13)	0.0037 (12)
C7	0.0460 (12)	0.0427 (11)	0.0458 (15)	−0.0004 (10)	0.0031 (11)	0.0003 (10)
C8	0.0477 (12)	0.0421 (11)	0.0420 (14)	0.0023 (10)	0.0000 (10)	0.0001 (10)
C9	0.0512 (13)	0.0416 (11)	0.0460 (15)	0.0024 (10)	0.0001 (11)	0.0051 (10)
C10	0.0546 (13)	0.0415 (11)	0.0489 (16)	0.0006 (10)	0.0092 (12)	0.0000 (10)
C11	0.059 (5)	0.075 (5)	0.054 (4)	0.005 (3)	0.015 (3)	0.025 (3)
C12	0.094 (4)	0.068 (3)	0.060 (4)	0.010 (2)	0.039 (3)	0.011 (2)
C13	0.093 (5)	0.068 (4)	0.044 (2)	0.006 (3)	0.014 (2)	0.002 (2)
S1	0.0714 (7)	0.0573 (7)	0.0508 (8)	0.0087 (5)	0.0071 (6)	0.0099 (5)
C10A	0.0546 (13)	0.0415 (11)	0.0489 (16)	0.0006 (10)	0.0092 (12)	0.0000 (10)
C11A	0.059 (5)	0.075 (5)	0.054 (4)	0.005 (3)	0.015 (3)	0.025 (3)
C12A	0.094 (4)	0.068 (3)	0.060 (4)	0.010 (2)	0.039 (3)	0.011 (2)
C13A	0.093 (5)	0.068 (4)	0.044 (2)	0.006 (3)	0.014 (2)	0.002 (2)
S1A	0.071 (4)	0.069 (4)	0.098 (6)	0.006 (3)	0.036 (3)	−0.001 (3)
C14	0.0519 (13)	0.0425 (11)	0.0463 (15)	0.0017 (10)	0.0010 (11)	−0.0027 (10)
C15	0.0533 (13)	0.0440 (12)	0.0468 (16)	0.0025 (10)	0.0033 (11)	0.0020 (11)
C16	0.0728 (17)	0.0510 (14)	0.060 (2)	0.0088 (12)	0.0102 (15)	0.0090 (13)
C17	0.0521 (13)	0.0418 (12)	0.0597 (17)	0.0001 (10)	−0.0035 (12)	0.0029 (12)
C18	0.0559 (14)	0.0411 (11)	0.0558 (17)	0.0089 (11)	−0.0029 (12)	0.0015 (11)
C19	0.0741 (17)	0.0475 (13)	0.067 (2)	0.0061 (12)	−0.0048 (15)	−0.0047 (13)
C20	0.097 (2)	0.0625 (17)	0.072 (2)	0.0120 (16)	−0.0090 (18)	−0.0148 (16)
C21	0.090 (2)	0.091 (2)	0.0546 (19)	0.0268 (18)	0.0018 (16)	−0.0118 (17)
C22	0.0669 (16)	0.0693 (17)	0.068 (2)	0.0111 (13)	0.0055 (15)	0.0039 (15)
C23	0.0561 (14)	0.0511 (13)	0.0575 (17)	0.0069 (11)	0.0026 (13)	−0.0037 (12)
C24	0.0474 (12)	0.0457 (12)	0.0557 (17)	0.0015 (10)	0.0007 (12)	−0.0056 (11)
C25	0.0745 (17)	0.0466 (13)	0.082 (2)	0.0090 (13)	0.0182 (16)	0.0003 (13)
C26	0.097 (2)	0.0545 (15)	0.104 (3)	0.0179 (15)	0.027 (2)	−0.0068 (17)
C27	0.084 (2)	0.0729 (19)	0.087 (3)	0.0185 (16)	0.0137 (18)	−0.0224 (17)
C28	0.0761 (18)	0.0809 (19)	0.065 (2)	0.0025 (15)	0.0133 (15)	−0.0117 (16)
C29	0.0709 (16)	0.0534 (14)	0.0627 (19)	−0.0001 (13)	0.0049 (14)	−0.0053 (13)
C30	0.0499 (12)	0.0371 (11)	0.0513 (16)	−0.0006 (10)	−0.0016 (11)	−0.0002 (10)
C31	0.0474 (12)	0.0379 (11)	0.0448 (14)	0.0013 (9)	−0.0009 (11)	−0.0001 (10)
C32	0.0521 (13)	0.0387 (11)	0.0540 (16)	0.0008 (10)	−0.0043 (11)	0.0026 (11)
C33	0.0613 (14)	0.0384 (11)	0.0509 (16)	−0.0025 (11)	−0.0009 (12)	0.0018 (10)
C34	0.0618 (15)	0.0544 (13)	0.0555 (18)	0.0046 (12)	0.0055 (13)	0.0064 (12)
C35	0.0865 (19)	0.0605 (15)	0.061 (2)	−0.0020 (15)	0.0208 (16)	0.0022 (14)
C36	0.116 (2)	0.0663 (17)	0.0457 (18)	−0.0002 (17)	0.0051 (17)	0.0080 (14)
C37	0.0492 (12)	0.0418 (11)	0.0486 (15)	0.0017 (10)	−0.0023 (11)	−0.0041 (10)
C38	0.0507 (13)	0.0399 (11)	0.0504 (16)	0.0028 (10)	−0.0028 (11)	0.0011 (10)
C39	0.0671 (16)	0.0449 (13)	0.0552 (19)	0.0044 (11)	0.0003 (14)	0.0042 (12)
C40	0.0518 (13)	0.0398 (12)	0.0646 (18)	0.0030 (10)	−0.0097 (13)	−0.0004 (12)
C41	0.0552 (14)	0.0476 (13)	0.0558 (17)	0.0141 (11)	−0.0117 (13)	−0.0083 (12)
C42	0.0811 (19)	0.0574 (15)	0.083 (2)	0.0195 (14)	−0.0205 (17)	−0.0231 (15)
C43	0.129 (3)	0.101 (3)	0.083 (3)	0.049 (2)	−0.027 (2)	−0.039 (2)
C44	0.130 (3)	0.135 (3)	0.050 (2)	0.075 (3)	−0.001 (2)	−0.010 (2)
C45	0.083 (2)	0.102 (2)	0.071 (2)	0.0371 (18)	0.0130 (18)	0.0130 (19)
C46	0.0611 (15)	0.0585 (15)	0.0593 (19)	0.0169 (12)	−0.0030 (14)	−0.0008 (13)
N1	0.0512 (10)	0.0408 (9)	0.0447 (13)	0.0035 (8)	0.0040 (9)	0.0014 (9)
N2	0.0565 (11)	0.0417 (10)	0.0464 (13)	0.0013 (9)	0.0077 (9)	0.0032 (9)
N3	0.133 (2)	0.0801 (17)	0.0608 (19)	0.0188 (15)	0.0272 (17)	0.0141 (14)
N4	0.0529 (11)	0.0400 (9)	0.0526 (14)	0.0031 (8)	0.0002 (10)	−0.0029 (9)
N5	0.0584 (11)	0.0415 (10)	0.0504 (14)	0.0036 (9)	0.0023 (10)	0.0014 (9)
N6	0.107 (2)	0.0762 (16)	0.0622 (18)	0.0028 (14)	0.0157 (15)	0.0054 (13)
O1	0.0846 (12)	0.0475 (9)	0.0808 (15)	0.0079 (9)	0.0140 (10)	0.0159 (9)
O2	0.0883 (13)	0.0453 (9)	0.0901 (16)	0.0088 (9)	0.0058 (11)	0.0160 (10)
S2	0.0886 (5)	0.0588 (4)	0.0618 (5)	0.0138 (3)	−0.0064 (4)	0.0098 (3)

Geometric parameters (Å, º) top

C1—C6	1.370 (3)	C22—C23	1.372 (4)
C1—C2	1.382 (3)	C22—H22	0.9300
C1—N1	1.431 (3)	C23—H23	0.9300
C2—C3	1.378 (3)	C24—C29	1.371 (3)
C2—H2	0.9300	C24—C25	1.381 (3)
C3—C4	1.361 (4)	C24—N4	1.429 (3)
C3—H3	0.9300	C25—C26	1.371 (4)
C4—C5	1.374 (3)	C25—H25	0.9300
C4—H4	0.9300	C26—C27	1.371 (4)
C5—C6	1.385 (3)	C26—H26	0.9300
C5—H5	0.9300	C27—C28	1.384 (4)
C6—H6	0.9300	C27—H27	0.9300
C7—N2	1.333 (3)	C28—C29	1.382 (4)
C7—C8	1.430 (3)	C28—H28	0.9300
C7—C10	1.450 (3)	C29—H29	0.9300
C7—C10A	1.450 (3)	C30—N5	1.328 (3)
C8—C9	1.384 (3)	C30—C31	1.430 (3)
C8—C14	1.439 (3)	C30—C33	1.455 (3)
C9—N1	1.339 (3)	C31—C32	1.377 (3)
C9—H9	0.9300	C31—C37	1.434 (3)
C10—C11	1.378 (10)	C32—N4	1.343 (3)
C10—S1	1.695 (3)	C32—H32	0.9300
C11—C12	1.444 (10)	C33—C34	1.376 (3)
C11—H11	0.9300	C33—S2	1.719 (2)
C12—C13	1.357 (5)	C34—C35	1.405 (3)
C12—H12	0.9300	C34—H34	0.9300
C13—S1	1.690 (4)	C35—C36	1.350 (4)
C13—H13	0.9300	C35—H35	0.9300
C10A—C11A	1.417 (15)	C36—S2	1.693 (3)
C10A—S1A	1.615 (10)	C36—H36	0.9300
C11A—C12A	1.425 (16)	C37—C38	1.355 (3)
C11A—H11A	0.9300	C37—H37	0.9300
C12A—C13A	1.336 (14)	C38—C39	1.425 (4)
C12A—H12A	0.9300	C38—C40	1.487 (3)
C13A—S1A	1.700 (14)	C39—N6	1.141 (3)
C13A—H13A	0.9300	C40—O2	1.225 (3)
C14—C15	1.359 (3)	C40—C41	1.476 (4)
C14—H14	0.9300	C41—C46	1.391 (3)
C15—C16	1.429 (4)	C41—C42	1.393 (3)
C15—C17	1.482 (3)	C42—C43	1.355 (5)
C16—N3	1.140 (3)	C42—H42	0.9300
C17—O1	1.224 (3)	C43—C44	1.367 (5)
C17—C18	1.480 (3)	C43—H43	0.9300
C18—C23	1.390 (3)	C44—C45	1.391 (5)
C18—C19	1.392 (3)	C44—H44	0.9300
C19—C20	1.365 (4)	C45—C46	1.371 (4)
C19—H19	0.9300	C45—H45	0.9300
C20—C21	1.383 (4)	C46—H46	0.9300
C20—H20	0.9300	N1—N2	1.361 (2)
C21—C22	1.380 (4)	N4—N5	1.365 (3)
C21—H21	0.9300

C6—C1—C2	120.7 (2)	C22—C23—C18	120.3 (2)
C6—C1—N1	120.6 (2)	C22—C23—H23	119.9
C2—C1—N1	118.8 (2)	C18—C23—H23	119.9
C3—C2—C1	119.0 (2)	C29—C24—C25	120.4 (2)
C3—C2—H2	120.5	C29—C24—N4	120.4 (2)
C1—C2—H2	120.5	C25—C24—N4	119.2 (2)
C4—C3—C2	121.1 (2)	C26—C25—C24	119.3 (3)
C4—C3—H3	119.5	C26—C25—H25	120.3
C2—C3—H3	119.5	C24—C25—H25	120.3
C3—C4—C5	119.6 (2)	C25—C26—C27	121.1 (3)
C3—C4—H4	120.2	C25—C26—H26	119.5
C5—C4—H4	120.2	C27—C26—H26	119.5
C4—C5—C6	120.5 (3)	C26—C27—C28	119.5 (3)
C4—C5—H5	119.7	C26—C27—H27	120.3
C6—C5—H5	119.7	C28—C27—H27	120.3
C1—C6—C5	119.2 (2)	C29—C28—C27	119.8 (3)
C1—C6—H6	120.4	C29—C28—H28	120.1
C5—C6—H6	120.4	C27—C28—H28	120.1
N2—C7—C8	110.9 (2)	C24—C29—C28	120.0 (2)
N2—C7—C10	119.2 (2)	C24—C29—H29	120.0
C8—C7—C10	129.8 (2)	C28—C29—H29	120.0
N2—C7—C10A	119.2 (2)	N5—C30—C31	111.5 (2)
C8—C7—C10A	129.8 (2)	N5—C30—C33	120.2 (2)
C9—C8—C7	103.97 (18)	C31—C30—C33	128.3 (2)
C9—C8—C14	130.5 (2)	C32—C31—C30	103.86 (18)
C7—C8—C14	125.6 (2)	C32—C31—C37	130.5 (2)
N1—C9—C8	107.7 (2)	C30—C31—C37	125.6 (2)
N1—C9—H9	126.2	N4—C32—C31	107.7 (2)
C8—C9—H9	126.2	N4—C32—H32	126.1
C11—C10—C7	127.7 (5)	C31—C32—H32	126.1
C11—C10—S1	111.5 (4)	C34—C33—C30	129.5 (2)
C7—C10—S1	120.64 (17)	C34—C33—S2	110.13 (19)
C10—C11—C12	111.1 (7)	C30—C33—S2	120.36 (17)
C10—C11—H11	124.4	C33—C34—C35	112.8 (2)
C12—C11—H11	124.4	C33—C34—H34	123.6
C13—C12—C11	112.3 (5)	C35—C34—H34	123.6
C13—C12—H12	123.9	C36—C35—C34	112.7 (3)
C11—C12—H12	123.9	C36—C35—H35	123.6
C12—C13—S1	111.9 (4)	C34—C35—H35	123.6
C12—C13—H13	124.1	C35—C36—S2	112.1 (2)
S1—C13—H13	124.1	C35—C36—H36	123.9
C13—S1—C10	93.1 (2)	S2—C36—H36	123.9
C11A—C10A—C7	120.4 (9)	C38—C37—C31	129.7 (2)
C11A—C10A—S1A	110.4 (9)	C38—C37—H37	115.2
C7—C10A—S1A	129.1 (5)	C31—C37—H37	115.2
C10A—C11A—C12A	111.9 (14)	C37—C38—C39	121.6 (2)
C10A—C11A—H11A	124.1	C37—C38—C40	123.3 (2)
C12A—C11A—H11A	124.1	C39—C38—C40	114.9 (2)
C13A—C12A—C11A	111.0 (16)	N6—C39—C38	179.2 (3)
C13A—C12A—H12A	124.5	O2—C40—C41	120.9 (2)
C11A—C12A—H12A	124.5	O2—C40—C38	118.6 (2)
C12A—C13A—S1A	111.6 (15)	C41—C40—C38	120.5 (2)
C12A—C13A—H13A	124.2	C46—C41—C42	119.3 (3)
S1A—C13A—H13A	124.2	C46—C41—C40	122.9 (2)
C10A—S1A—C13A	94.6 (9)	C42—C41—C40	117.8 (3)
C15—C14—C8	128.8 (2)	C43—C42—C41	120.3 (3)
C15—C14—H14	115.6	C43—C42—H42	119.8
C8—C14—H14	115.6	C41—C42—H42	119.8
C14—C15—C16	121.5 (2)	C42—C43—C44	120.0 (3)
C14—C15—C17	123.8 (2)	C42—C43—H43	120.0
C16—C15—C17	114.6 (2)	C44—C43—H43	120.0
N3—C16—C15	179.0 (3)	C43—C44—C45	121.2 (4)
O1—C17—C18	120.6 (2)	C43—C44—H44	119.4
O1—C17—C15	119.2 (2)	C45—C44—H44	119.4
C18—C17—C15	120.2 (2)	C46—C45—C44	118.8 (3)
C23—C18—C19	119.0 (2)	C46—C45—H45	120.6
C23—C18—C17	122.8 (2)	C44—C45—H45	120.6
C19—C18—C17	118.1 (2)	C45—C46—C41	120.3 (3)
C20—C19—C18	120.5 (3)	C45—C46—H46	119.8
C20—C19—H19	119.7	C41—C46—H46	119.8
C18—C19—H19	119.7	C9—N1—N2	112.32 (18)
C19—C20—C21	120.1 (3)	C9—N1—C1	128.2 (2)
C19—C20—H20	120.0	N2—N1—C1	119.48 (17)
C21—C20—H20	120.0	C7—N2—N1	105.10 (17)
C22—C21—C20	120.0 (3)	C32—N4—N5	112.28 (18)
C22—C21—H21	120.0	C32—N4—C24	127.8 (2)
C20—C21—H21	120.0	N5—N4—C24	119.83 (17)
C23—C22—C21	120.0 (3)	C30—N5—N4	104.61 (18)
C23—C22—H22	120.0	C36—S2—C33	92.24 (14)
C21—C22—H22	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C34—H34···O2ⁱ	0.93	2.61	3.396 (3)	143
C46—H46···O2ⁱ	0.93	2.45	3.363 (3)	167

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Footnotes

‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.

Funding information

The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.

References

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