3-{2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]thia­zol-4-yl}-3,8a-di­hydro-2H-chromen-2-one

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

doi:10.1107/S2414314619001706

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190170

https://doi.org/10.1107/S2414314619001706

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3-{2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]thiazol-4-yl}-3,8a-dihydro-2H-chromen-2-one

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

^aDepartment 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, ^dPharmaceutical Chemistry Department, College of Pharmacy, Umm Al-Qura University, Makkah, 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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 January 2019; accepted 30 January 2019; online 12 February 2019)

The title compound, C₂₇H₁₇ClFN₃O₂S, comprises chromonyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) rings with twist angles between the planes of adjacent rings pairs A/B, B/C, C/D and C/E of 14.1 (1), 18.2 (2), 1.3 (1) and 4.9 (1)°, respectively. The crystal structure is characterized by a range of intermolecular interactions including C—H⋯F, C—H⋯Cl and C—H⋯O contacts. Aromatic π–π stacking between chromonyl groups and chlorophenyl groups [centroid–centroid separations = 3.7170 (16) and 4.017 (2) Å, respectively] lead to columns of molecules propagating parallel to the [100] direction.

Keywords: crystal structure; chromen-2-one; pyrazole.

CCDC reference: 1894531

Structure description

Coumarins act as anticoagulant drugs (O'Reilly & Aggeler, 1968 ). Thiazoles are an essential core scaffold in many natural products (Chhabria et al., 2016 ) and pyrazoles have a broad spectrum of biological activities (Faria et al., 2017 ). We now describe the synthesis and structure of the title compound.

The asymmetric unit consists of one molecule, which comprises chromonyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) rings (Fig. 1). The twist angles between the planes through neighbouring rings pairs A/B, B/C, C/D and C/E are 14.1 (1), 18.2 (2), 1.3 (1) and 4.9 (1)°, respectively. The stereogenic centre C13 has an S configuration in the arbitrarily chosen asymmetric unit, but the crystal symmetry generates a racemic mixture.

Figure 1
The molecular structure of the title compound showing 50% displacement ellipsoids.

The extended structure is characterized by a range of intermolecular interactions including C—H⋯F, C—H⋯Cl and C—H⋯O contacts (Table 1, Fig. 2). Aromatic π–π stacking between chromonyl groups [with centroid-to-centroid distances of 3.7170 (16) Å] and between chlorophenyl groups [with ring-centroid separations of 4.017 (2) Å] lead to the formation of columns propagating in the [100] direction (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯F1ⁱ	0.98	2.47	3.372 (4)	154
C20—H20⋯Cl1ⁱⁱ	0.93	2.98	3.829 (4)	153
C26—H26⋯O2ⁱⁱⁱ	0.93	2.54	3.282 (4)	137
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A segment of the crystal structure showing intermolecular contacts as dotted lines.

Figure 3
The crystal structure viewed down the a-axis direction.

Synthesis and crystallization

The title compound was synthesized from the condensation of 3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.67 g, 2.0 mmol) with 3-(2-bromoacetyl)-3,8a-dihydro-2H-chromen-2-one (0.54 g, 2.0 mmol) in anhydrous ethanol (20 ml) under reflux for 2 h. The formed solid was recrystallized from dimethylformamide solution to give colourless blocks (83%), m.p. 228–230°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₇H₁₇ClFN₃O₂S
M_r	501.95
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	7.9243 (5), 23.7112 (9), 24.9270 (15)
V (Å³)	4683.7 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.31 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.997, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	21351, 5809, 3055
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.184, 1.04
No. of reflections	5809
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.58
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1894531

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001706/hb4283sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001706/hb4283Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619001706/hb4283Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 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 and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).

3-{2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]thiazol-4-yl}-3,8a-dihydro-2H-chromen-2-one top

Crystal data top

C₂₇H₁₇ClFN₃O₂S	D_x = 1.424 Mg m⁻³
M_r = 501.95	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3797 reflections
a = 7.9243 (5) Å	θ = 4.0–25.8°
b = 23.7112 (9) Å	µ = 0.29 mm⁻¹
c = 24.9270 (15) Å	T = 296 K
V = 4683.7 (4) Å³	Block, colourless
Z = 8	0.31 × 0.18 × 0.14 mm
F(000) = 2064

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	3055 reflections with I > 2σ(I)
ω scans	R_int = 0.044
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	θ_max = 29.9°, θ_min = 3.4°
T_min = 0.997, T_max = 0.998	h = −10→11
21351 measured reflections	k = −32→24
5809 independent reflections	l = −28→31

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.058	w = 1/[σ²(F_o²) + (0.0699P)² + 1.7487P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.184	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.64 e Å⁻³
5809 reflections	Δρ_min = −0.58 e Å⁻³
317 parameters	Extinction correction: SHELXL-2018/1 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0020 (4)
Primary atom site location: structure-invariant direct methods

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 in calculated positions and refined using a riding model. Bond distances for sp² C—H hydrogen atoms were set to 0.93 Å and their U_iso set to 1.2 times U_eq(C). Bond distances for methine and methylene C—H hydrogen atoms were set to 0.98 Å and 0.97 Å respectively and their U_iso set to 1.2 times U_eq(C).

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

	x	y	z	U_iso*/U_eq
C1	0.6165 (5)	0.40241 (12)	0.44274 (13)	0.0673 (9)
C2	0.6420 (3)	0.38786 (11)	0.49852 (12)	0.0527 (7)
C3	0.7055 (4)	0.42696 (11)	0.53236 (13)	0.0599 (8)
H3	0.723831	0.417008	0.567977	0.072*
C4	0.7455 (4)	0.48295 (11)	0.51563 (13)	0.0606 (8)
C5	0.7184 (4)	0.49645 (12)	0.46241 (13)	0.0630 (8)
C6	0.8068 (5)	0.52546 (13)	0.54907 (16)	0.0795 (10)
H6	0.826003	0.517879	0.585166	0.095*
C7	0.8392 (5)	0.57845 (14)	0.52916 (17)	0.0845 (11)
H7	0.880402	0.606465	0.551749	0.101*
C8	0.8110 (5)	0.58998 (14)	0.47617 (17)	0.0843 (11)
H8	0.833890	0.625898	0.463070	0.101*
C9	0.7497 (5)	0.54977 (13)	0.44212 (16)	0.0811 (10)
H9	0.729519	0.557999	0.406213	0.097*
C10	0.5992 (4)	0.33085 (11)	0.51677 (11)	0.0512 (7)
C11	0.5060 (4)	0.29166 (12)	0.49111 (13)	0.0590 (7)
H11	0.458704	0.296635	0.457296	0.071*
C12	0.6074 (4)	0.26392 (11)	0.57715 (12)	0.0527 (7)
C13	0.6996 (4)	0.26833 (11)	0.67224 (12)	0.0543 (7)
H13	0.622678	0.300241	0.677451	0.065*
C14	0.6679 (4)	0.22431 (12)	0.71584 (13)	0.0623 (8)
H14A	0.773301	0.210687	0.730791	0.075*
H14B	0.599109	0.239701	0.744513	0.075*
C15	0.5765 (4)	0.17823 (11)	0.68671 (12)	0.0549 (7)
C16	0.8778 (3)	0.28972 (10)	0.66887 (11)	0.0484 (6)
C17	1.0059 (4)	0.25844 (13)	0.64682 (13)	0.0647 (8)
H17	0.982862	0.222720	0.633272	0.078*
C18	1.1688 (5)	0.27924 (19)	0.64442 (16)	0.0850 (11)
H18	1.255418	0.258144	0.629208	0.102*
C19	1.1984 (5)	0.3308 (2)	0.66472 (18)	0.0861 (11)
C20	1.0797 (5)	0.36238 (15)	0.68832 (17)	0.0872 (11)
H20	1.106018	0.397365	0.702961	0.105*
C21	0.9171 (4)	0.34161 (11)	0.69032 (14)	0.0676 (9)
H21	0.832787	0.362996	0.706419	0.081*
C22	0.5073 (4)	0.12765 (11)	0.71181 (12)	0.0539 (7)
C23	0.4302 (4)	0.08538 (12)	0.68196 (14)	0.0683 (8)
H23	0.422286	0.088981	0.644896	0.082*
C24	0.3655 (5)	0.03834 (13)	0.70667 (15)	0.0751 (10)
H24	0.314270	0.010204	0.686412	0.090*
C25	0.3768 (5)	0.03306 (11)	0.76113 (15)	0.0700 (9)
C26	0.4514 (5)	0.07388 (12)	0.79203 (14)	0.0706 (9)
H26	0.458289	0.069842	0.829072	0.085*
C27	0.5162 (4)	0.12107 (12)	0.76704 (13)	0.0637 (8)
H27	0.566947	0.149040	0.787635	0.076*
N1	0.6574 (3)	0.31478 (9)	0.56682 (9)	0.0545 (6)
N3	0.6491 (3)	0.23679 (9)	0.62379 (10)	0.0629 (7)
N5	0.5655 (3)	0.18683 (9)	0.63576 (11)	0.0607 (6)
O1	0.6566 (3)	0.45689 (8)	0.42704 (9)	0.0774 (7)
O2	0.5641 (4)	0.37238 (9)	0.40796 (10)	0.0963 (9)
S1	0.48577 (10)	0.23142 (3)	0.52875 (3)	0.0601 (3)
Cl1	0.29654 (18)	−0.02666 (4)	0.79278 (5)	0.1103 (4)
F1	1.3583 (3)	0.35259 (13)	0.66200 (13)	0.1451 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.101 (2)	0.0501 (15)	0.051 (2)	−0.0008 (16)	−0.0030 (17)	0.0017 (14)
C2	0.0635 (16)	0.0520 (14)	0.0427 (18)	0.0052 (13)	0.0025 (13)	0.0007 (12)
C3	0.078 (2)	0.0568 (15)	0.0448 (18)	−0.0010 (15)	−0.0017 (15)	−0.0005 (13)
C4	0.0722 (19)	0.0532 (15)	0.057 (2)	0.0002 (14)	0.0046 (16)	0.0007 (14)
C5	0.081 (2)	0.0504 (15)	0.057 (2)	0.0040 (15)	0.0025 (16)	−0.0009 (14)
C6	0.109 (3)	0.0625 (19)	0.067 (2)	−0.0128 (18)	−0.001 (2)	−0.0054 (16)
C7	0.109 (3)	0.0623 (19)	0.082 (3)	−0.0137 (19)	−0.001 (2)	−0.0077 (18)
C8	0.112 (3)	0.0541 (17)	0.087 (3)	−0.0056 (18)	0.008 (2)	0.0085 (18)
C9	0.115 (3)	0.0567 (17)	0.071 (3)	−0.0001 (19)	−0.001 (2)	0.0081 (16)
C10	0.0621 (17)	0.0509 (13)	0.0404 (17)	0.0058 (13)	−0.0005 (13)	−0.0007 (12)
C11	0.0741 (19)	0.0576 (16)	0.0453 (18)	−0.0008 (14)	−0.0093 (14)	−0.0016 (13)
C12	0.0600 (16)	0.0534 (15)	0.0447 (17)	−0.0003 (13)	−0.0018 (13)	0.0017 (12)
C13	0.0659 (17)	0.0482 (13)	0.0488 (18)	0.0010 (13)	−0.0046 (13)	−0.0015 (12)
C14	0.074 (2)	0.0609 (16)	0.052 (2)	−0.0109 (15)	−0.0033 (15)	0.0034 (14)
C15	0.0635 (17)	0.0495 (14)	0.052 (2)	−0.0002 (13)	−0.0052 (14)	0.0013 (13)
C16	0.0613 (16)	0.0444 (13)	0.0397 (16)	0.0052 (12)	−0.0026 (12)	0.0008 (11)
C17	0.084 (2)	0.0634 (17)	0.0468 (19)	0.0155 (16)	0.0023 (15)	−0.0049 (14)
C18	0.071 (2)	0.119 (3)	0.065 (3)	0.031 (2)	0.0178 (18)	0.014 (2)
C19	0.059 (2)	0.111 (3)	0.088 (3)	−0.009 (2)	−0.0010 (19)	0.033 (2)
C20	0.087 (3)	0.068 (2)	0.106 (3)	−0.022 (2)	−0.012 (2)	0.003 (2)
C21	0.071 (2)	0.0489 (15)	0.083 (3)	0.0014 (15)	0.0023 (18)	−0.0112 (14)
C22	0.0671 (18)	0.0478 (14)	0.0468 (18)	0.0010 (13)	−0.0023 (13)	0.0013 (12)
C23	0.095 (2)	0.0564 (16)	0.053 (2)	−0.0090 (17)	−0.0010 (17)	−0.0058 (14)
C24	0.106 (3)	0.0536 (16)	0.066 (3)	−0.0150 (17)	0.0013 (19)	−0.0111 (15)
C25	0.092 (2)	0.0509 (15)	0.067 (2)	−0.0062 (16)	0.0103 (18)	0.0031 (15)
C26	0.099 (2)	0.0604 (17)	0.052 (2)	−0.0064 (17)	0.0027 (17)	0.0030 (15)
C27	0.081 (2)	0.0543 (15)	0.056 (2)	−0.0049 (14)	−0.0059 (16)	0.0016 (14)
N1	0.0670 (14)	0.0523 (12)	0.0442 (15)	−0.0023 (11)	−0.0048 (11)	0.0024 (10)
N3	0.0846 (17)	0.0538 (13)	0.0503 (16)	−0.0152 (12)	−0.0163 (13)	0.0064 (11)
N5	0.0790 (17)	0.0497 (12)	0.0534 (17)	−0.0092 (12)	−0.0080 (13)	0.0029 (11)
O1	0.125 (2)	0.0554 (11)	0.0522 (14)	−0.0044 (12)	−0.0058 (13)	0.0056 (10)
O2	0.172 (3)	0.0663 (13)	0.0507 (15)	−0.0200 (16)	−0.0255 (16)	0.0004 (11)
S1	0.0744 (5)	0.0541 (4)	0.0517 (5)	−0.0075 (3)	−0.0083 (4)	−0.0012 (3)
Cl1	0.1708 (11)	0.0635 (5)	0.0965 (9)	−0.0316 (6)	0.0262 (7)	0.0075 (5)
F1	0.0697 (14)	0.196 (3)	0.170 (3)	−0.0305 (16)	−0.0078 (16)	0.066 (2)

Geometric parameters (Å, º) top

C1—O2	1.196 (4)	C14—C15	1.499 (4)
C1—O1	1.386 (3)	C14—H14A	0.9700
C1—C2	1.447 (4)	C14—H14B	0.9700
C2—C3	1.351 (4)	C15—N5	1.289 (4)
C2—C10	1.466 (4)	C15—C22	1.459 (4)
C3—C4	1.427 (4)	C16—C17	1.372 (4)
C3—H3	0.9300	C16—C21	1.377 (4)
C4—C5	1.381 (4)	C17—C18	1.383 (5)
C4—C6	1.395 (4)	C17—H17	0.9300
C5—O1	1.377 (4)	C18—C19	1.344 (5)
C5—C9	1.384 (4)	C18—H18	0.9300
C6—C7	1.375 (4)	C19—C20	1.338 (6)
C6—H6	0.9300	C19—F1	1.370 (4)
C7—C8	1.367 (5)	C20—C21	1.380 (5)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.366 (5)	C21—H21	0.9300
C8—H8	0.9300	C22—C27	1.387 (4)
C9—H9	0.9300	C22—C23	1.390 (4)
C10—C11	1.348 (4)	C23—C24	1.373 (4)
C10—N1	1.384 (3)	C23—H23	0.9300
C11—S1	1.716 (3)	C24—C25	1.366 (5)
C11—H11	0.9300	C24—H24	0.9300
C12—N1	1.295 (3)	C25—C26	1.371 (4)
C12—N3	1.369 (4)	C25—Cl1	1.741 (3)
C12—S1	1.726 (3)	C26—C27	1.380 (4)
C13—N3	1.476 (4)	C26—H26	0.9300
C13—C16	1.503 (4)	C27—H27	0.9300
C13—C14	1.528 (4)	N3—N5	1.389 (3)
C13—H13	0.9800

O2—C1—O1	115.4 (3)	H14A—C14—H14B	109.0
O2—C1—C2	127.1 (3)	N5—C15—C22	121.8 (3)
O1—C1—C2	117.5 (3)	N5—C15—C14	113.2 (2)
C3—C2—C1	119.2 (3)	C22—C15—C14	125.0 (3)
C3—C2—C10	121.7 (3)	C17—C16—C21	118.1 (3)
C1—C2—C10	119.1 (2)	C17—C16—C13	122.4 (3)
C2—C3—C4	122.6 (3)	C21—C16—C13	119.5 (3)
C2—C3—H3	118.7	C16—C17—C18	121.0 (3)
C4—C3—H3	118.7	C16—C17—H17	119.5
C5—C4—C6	117.4 (3)	C18—C17—H17	119.5
C5—C4—C3	117.5 (3)	C19—C18—C17	118.1 (3)
C6—C4—C3	125.1 (3)	C19—C18—H18	121.0
O1—C5—C4	120.8 (3)	C17—C18—H18	121.0
O1—C5—C9	116.9 (3)	C20—C19—C18	123.5 (3)
C4—C5—C9	122.3 (3)	C20—C19—F1	117.5 (4)
C7—C6—C4	120.6 (3)	C18—C19—F1	119.0 (4)
C7—C6—H6	119.7	C19—C20—C21	118.2 (3)
C4—C6—H6	119.7	C19—C20—H20	120.9
C8—C7—C6	120.1 (3)	C21—C20—H20	120.9
C8—C7—H7	120.0	C16—C21—C20	121.1 (3)
C6—C7—H7	120.0	C16—C21—H21	119.5
C9—C8—C7	121.3 (3)	C20—C21—H21	119.5
C9—C8—H8	119.4	C27—C22—C23	118.2 (3)
C7—C8—H8	119.4	C27—C22—C15	119.9 (3)
C8—C9—C5	118.3 (3)	C23—C22—C15	121.9 (3)
C8—C9—H9	120.8	C24—C23—C22	120.7 (3)
C5—C9—H9	120.8	C24—C23—H23	119.7
C11—C10—N1	114.9 (2)	C22—C23—H23	119.7
C11—C10—C2	127.9 (3)	C25—C24—C23	119.7 (3)
N1—C10—C2	117.2 (2)	C25—C24—H24	120.1
C10—C11—S1	111.4 (2)	C23—C24—H24	120.1
C10—C11—H11	124.3	C24—C25—C26	121.4 (3)
S1—C11—H11	124.3	C24—C25—Cl1	120.1 (3)
N1—C12—N3	122.2 (3)	C26—C25—Cl1	118.5 (3)
N1—C12—S1	116.6 (2)	C25—C26—C27	118.7 (3)
N3—C12—S1	121.2 (2)	C25—C26—H26	120.7
N3—C13—C16	112.3 (2)	C27—C26—H26	120.7
N3—C13—C14	101.0 (2)	C26—C27—C22	121.3 (3)
C16—C13—C14	115.1 (2)	C26—C27—H27	119.3
N3—C13—H13	109.3	C22—C27—H27	119.3
C16—C13—H13	109.3	C12—N1—C10	109.5 (2)
C14—C13—H13	109.3	C12—N3—N5	117.9 (2)
C15—C14—C13	103.5 (2)	C12—N3—C13	121.5 (2)
C15—C14—H14A	111.1	N5—N3—C13	112.7 (2)
C13—C14—H14A	111.1	C15—N5—N3	108.3 (2)
C15—C14—H14B	111.1	C5—O1—C1	122.3 (3)
C13—C14—H14B	111.1	C11—S1—C12	87.62 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F1ⁱ	0.98	2.47	3.372 (4)	154
C20—H20···Cl1ⁱⁱ	0.93	2.98	3.829 (4)	153
C26—H26···O2ⁱⁱⁱ	0.93	2.54	3.282 (4)	137

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

Footnotes

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

Acknowledgements

The authors thank Umm Al-Qura and Cardiff Universities for their support.

Funding information

Funding for this research was provided by: Deanship of Scientific Research at Umm Al-Qura University (award No. 17-MED-1-03-0007).

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