3-(Benzo[d]thia­zol-2-yl)-2H-chromen-2-one

Abdallah, A.E.M.; Elgemeie, G.H.; Jones, P.G.

doi:10.1107/S2414314622003327

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 3| March 2022| x220332

https://doi.org/10.1107/S2414314622003327

Open

access

3-(Benzo[d]thiazol-2-yl)-2H-chromen-2-one

Amira E. M. Abdallah,^a Galal H. Elgemeie ^a and Peter G. Jones ^b ^*

^aChemistry Department, Faculty of Science, Helwan University, Cairo, Egypt, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
^*Correspondence e-mail: p.jones@tu-bs.de

Edited by C. Massera, Università di Parma, Italy (Received 17 March 2022; accepted 24 March 2022; online 31 March 2022)

In the title compound, C₁₆H₉NO₂S, the interplanar angle is 6.47 (6)°. An intramolecular S⋯O=C contact of 2.727 (2) Å is observed. The packing is determined by several types of weak interaction (`weak' hydrogen bonds, S⋯S contacts and π–π stacking).

Keywords: benzothiazol; coumarin; chromene; crystal structure.

CCDC reference: 2161632

Structure description

Coumarin (chromen-2-one) derivatives represent a significant class of organic heterocycles; they can be found in various natural or synthetic drug compounds and display a variety of biological activities (Curini et al., 2006 ), the most noticeable of which are photobiological properties upon irradiation with UV light. Thus, many coumarin derivatives are effective photosensitizers with valuable applications in medicine (Bansal et al., 2013 ). Because of these photochemical characteristics, together with their practical stability, ease of synthesis and good solubility, coumarins have been widely explored as solar energy collectors, charge-transfer agents and non-linear optical materials for photonic and electronic applications (Kim et al., 2011 ). Coumarins are one of the most broadly investigated and commercially important classes of organic fluorescent materials. Coumarin dyes fluoresce in the blue–green spectroscopic region and are commonly used in daylight fluorescent pigments, fluorescent probes, and as tunable dye lasers or organic light-emitting diodes (Christie & Lui, 2000 ). The emission intensity of coumarin chromophores strongly depends on the nature and position of their substituents (Żamojć et al., 2014 ).

Benzothiazole derivatives also exhibit strong luminescence in solution and in the solid state. Molecules that incorporate benzothiazoles have attracted considerable research interest in the field of organic light-emitting diodes because of their unique electro-optical properties (Wang et al., 2010 ). Recently, we have synthesized some benzothiazoles (Azzam et al., 2017a ,b , 2020a ,b ,c , 2021 ; Elgemeie et al., 2000a ,b ) and coumarin derivatives (Elgemeie, 1989 ; Elgemeie & Elghandour, 1990 ; Elgemeie et al., 2015 ).

As a continuation of our research interest in exploiting new coumarin and benzothiazole derivatives for light-emitting materials, we describe here the synthesis and characterization of a benzothiazole-based coumarin compound. The reaction of N-[2-(benzo[d]thiazol-2-yl)acetyl]benzohydrazide (1) with salicylaldehde (2) was investigated. This gave a product whose mass spectrum was not consistent with the proposed structure N-(3-(benzo[d]thiazol-2-yl)-2-oxoquinolin-1(2H)-yl)benzamide (5). Therefore the X-ray crystal structure was determined, revealing that 3-(benzo[d]thiazol-2-yl)-2H-chromen-2-one (4) is the sole product in the solid state (Fig. 1). The formation of (4) is assumed to proceed via initial formation of adduct (3) and elimination of benzohydrazide rather than water.

Figure 1
Reaction scheme.

The structure of 4 is shown in Fig. 2. Molecular dimensions may be regarded as normal; a brief selection is presented in Table 1. The ring systems are essentially planar, with r.m.s. deviations of 0.012 Å for the benzothiazole and 0.006 Å for the chromene (including the exocyclic oxygen atom); the interplanar angle is 6.47 (6)°. The intramolecular contact distance S1⋯O2 is 2.727 (2) Å.

Table 1
Selected geometric parameters (Å, °)

S1—C7A	1.733 (2)	C8—C16	1.357 (3)
S1—C2	1.758 (2)	C8—C9	1.470 (3)
C2—N3	1.308 (3)	C9—O1	1.365 (3)
N3—C3A	1.380 (3)	C10—O1	1.379 (2)
C3A—C7A	1.411 (3)	C15—C16	1.434 (3)

C7A—S1—C2	88.87 (10)	N3—C3A—C7A	115.15 (19)
N3—C2—S1	115.63 (16)	C3A—C7A—S1	109.57 (16)
C2—N3—C3A	110.75 (18)

Figure 2
The molecule of 4 in the crystal. Ellipsoids represent 50% probability levels.

There are three short intermolecular H⋯O/H⋯N contacts (Table 2), the shortest of which could reasonably be regarded as a `weak' hydrogen bond. Together with an S1⋯S1 contact [3.626 (1) Å, operator −x, 1 − y, 1 − z], this links the molecules to form corrugated sheets lying parallel to the bc plane (Fig. 3). However, this is only one way of considering the packing. The rings also display short contacts between their centroids via x-axis translation [thiazole⋯(benzothiazole benzo) 3.6187 (13) Å, thiazole⋯(coumarin heterocycle) 3.5344 (12) Å, (coumarin heterocycle)⋯(coumarin benzo) 3.4148 (12) Å], although the stacking is somewhat offset. Viewed parallel to the c axis, the rings are seen edge-on in a herringbone pattern.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1ⁱ	0.95	2.46	3.383 (3)	163
C11—H11⋯N3ⁱⁱ	0.95	2.63	3.523 (3)	156
C13—H13⋯O2ⁱⁱⁱ	0.95	2.65	3.314 (3)	127
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 3
Crystal packing of 4 viewed parallel to the short a axis. Dashed lines indicate `weak' hydrogen bonds or S⋯S contacts. Hydrogen atoms not involved in hydrogen bonding are omitted.

A search of the Cambridge Database (Version 2021.3.0; Groom et al., 2016 ) for purely organic coumarin derivatives gave 1030 hits with 1299 individual molecules. The mean bond lengths of the coumarin heterocycle (referred to the numbering of 4) are: C15—C16 = 1.442 (15), C16—C8 =1.356 (19), C8—C9 =1.448 (18), C9—O1 =1.375 (14) and O1—C10 =1.378 (11) Å, and the values in 4 (Table 1) are consistent with these mean values. A more specialized search revealed four compounds with simple coumarin derivatives linked to benzo[d]thiazol in the same way as in 4: DARPIX (Ezeh & Harrop, 2012 ), VIVWEF and VIWDOX (Shi et al., 2019 ), WINZAU (Jasinski & Paight, 1995 ). The first three have been used as fluorescent probes, for the detection of biothiols and the evaluation of anti-cancer agents, respectively.

Synthesis and crystallization

A mixture of N-[2-(benzo[d]thiazol-2-yl)acetyl]benzohydrazide 1 (3.11 g, 0.01 mol), salicylaldehyde 2 (1.22 g, 0.01 mol) and ammonium acetate (0.77 g, 0.01 mol) in ethanol (10 mL) was refluxed for 3 h. The precipitate was filtered off and recrystallized from ethanol solution to give pale-yellow crystals in 95% yield, m.p. 501–503 K; IR (KBr, cm⁻¹): υ 3048, 3028 (CH-aromatic), 1715 (C=O), 1557 (C=N) and 1602, 1479 (C=C). ¹H NMR (400 MHz DMSO-d₆) δ: 7.46–8.21 (m, 8H, 2C₆H₄), 9.26 (s, 1H, CH-pyran). ¹³C NMR (100 MHz, DMSO-d₆) δ: 116.7, 119.2, 119.8, 122.7, 123.0, 125.7, 125.9, 127.2, 130.7, 134.2, 136.4, 142.5, 152.4, 153.8 (aromatic carbons), 159.9 (C=N), 160.1 (C=O). MS (EI): m/z (%) 281 [M⁺+2] (0.44), 280 [M⁺+1] (0.96), 279 [M⁺] (4.06), 278 [M⁺−1] (0.12), 277 [M⁺−2] (0.17), 105 (100.00), 77 [C₆H₅]⁺ (58.06). Analysis: calculated for C₁₆H₉NO₂S (279.31): C 68.80; H 3.25; N 5.01; S 11.48%. Found: C 68.70; H 3.33; N 5.12; S 11.60%.

The sample consisted of a mass of long, extremely fine needles with an overall matt appearance. Careful separation and cutting provided a single crystal, which proved to be measurable using a high-intensity X-ray source.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₆H₉NO₂S
M_r	279.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	4.60717 (11), 20.7275 (5), 12.6444 (3)
β (°)	91.911 (2)
V (Å³)	1206.81 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.39
Crystal size (mm)	0.04 × 0.01 × 0.01

Data collection
Diffractometer	XtaLAB Synergy
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.696, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	49602, 2547, 2528
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.120, 1.25
No. of reflections	2547
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.43
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015b ), SHELXL2018/3 (Sheldrick, 2015a ) and XP (Siemens, 1994 ).

Structural data

CCDC reference: 2161632

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314622003327/xi4003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622003327/xi4003Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622003327/xi4003Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015a); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015a).

3-(Benzo[d]thiazol-2-yl)-2H-chromen-2-one top

Crystal data top

C₁₆H₉NO₂S	F(000) = 576
M_r = 279.30	D_x = 1.537 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 4.60717 (11) Å	Cell parameters from 20622 reflections
b = 20.7275 (5) Å	θ = 4.1–76.8°
c = 12.6444 (3) Å	µ = 2.38 mm⁻¹
β = 91.911 (2)°	T = 100 K
V = 1206.81 (5) Å³	Needle, pale yellow
Z = 4	0.04 × 0.01 × 0.01 mm

Data collection top

XtaLAB Synergy diffractometer	2547 independent reflections
Radiation source: micro-focus sealed X-ray tube	2528 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.068
ω scans	θ_max = 77.9°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −5→5
T_min = 0.696, T_max = 1.000	k = −24→26
49602 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0479P)² + 1.2289P] where P = (F_o² + 2F_c²)/3
S = 1.25	(Δ/σ)_max = 0.001
2547 reflections	Δρ_max = 0.45 e Å⁻³
181 parameters	Δρ_min = −0.43 e Å⁻³
0 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.3898 (0.0014) x + 13.7552 (0.0080) y + 2.0177 (0.0070) z = 8.9676 (0.0037)

* 0.0227 (0.0011) S1 * 0.0005 (0.0015) C2 * -0.0077 (0.0015) N3 * -0.0083 (0.0019) C3A * 0.0016 (0.0017) C4 * 0.0176 (0.0017) C5 * 0.0019 (0.0017) C6 * -0.0169 (0.0016) C7 * -0.0115 (0.0018) C7A

Rms deviation of fitted atoms = 0.0124

- 3.2516 (0.0012) x + 14.6654 (0.0053) y + 0.7477 (0.0068) z = 9.1325 (0.0065)

Angle to previous plane (with approximate esd) = 6.467 ( 0.060 )

* -0.0054 (0.0017) C8 * -0.0016 (0.0018) C9 * 0.0001 (0.0019) C10 * -0.0072 (0.0017) C11 * 0.0011 (0.0017) C12 * -0.0035 (0.0017) C13 * -0.0017 (0.0017) C14 * 0.0079 (0.0019) C15 * 0.0022 (0.0016) C16 * 0.0136 (0.0014) O1 * -0.0054 (0.0014) O2

Rms deviation of fitted atoms = 0.0059

#======================================================================

Short contact:

3.6259 (0.0010) S1 - S1_$4

Operator $4: -x, 1-y, 1-z

Refinement. The hydrogen atoms were included using a riding model starting from calculated positions (C—H_aromatic 0.95 Å). The U(H) values were fixed at 1.2 times the equivalent U_iso value of the parent carbon atoms.

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

	x	y	z	U_iso*/U_eq
S1	−0.03347 (11)	0.58024 (2)	0.44385 (4)	0.01871 (16)
C2	0.1290 (5)	0.63202 (10)	0.35289 (16)	0.0179 (4)
N3	0.0429 (4)	0.62471 (9)	0.25396 (14)	0.0190 (4)
C3A	−0.1604 (5)	0.57600 (10)	0.24410 (17)	0.0197 (4)
C4	−0.3012 (5)	0.55593 (11)	0.14936 (17)	0.0227 (5)
H4	−0.257833	0.575871	0.084112	0.027*
C5	−0.5025 (5)	0.50703 (11)	0.15244 (18)	0.0238 (5)
H5	−0.600561	0.493791	0.088821	0.029*
C6	−0.5657 (5)	0.47627 (11)	0.24818 (18)	0.0230 (5)
H6	−0.704244	0.442317	0.248094	0.028*
C7	−0.4295 (5)	0.49470 (10)	0.34205 (18)	0.0208 (4)
H7	−0.471183	0.473769	0.406635	0.025*
C7A	−0.2284 (5)	0.54501 (10)	0.33950 (16)	0.0189 (4)
C8	0.3479 (4)	0.67984 (10)	0.38551 (16)	0.0174 (4)
C9	0.4134 (5)	0.68882 (10)	0.49914 (16)	0.0186 (4)
C10	0.7662 (5)	0.76940 (10)	0.45552 (16)	0.0174 (4)
C11	0.9720 (5)	0.81249 (10)	0.49547 (16)	0.0200 (4)
H11	1.009311	0.816281	0.569554	0.024*
C12	1.1223 (5)	0.84998 (10)	0.42467 (17)	0.0208 (4)
H12	1.262170	0.880282	0.450509	0.025*
C13	1.0693 (5)	0.84351 (10)	0.31510 (17)	0.0202 (4)
H13	1.174863	0.869054	0.267249	0.024*
C14	0.8647 (5)	0.80021 (10)	0.27695 (16)	0.0191 (4)
H14	0.830301	0.796009	0.202773	0.023*
C15	0.7059 (4)	0.76208 (10)	0.34688 (16)	0.0173 (4)
C16	0.4906 (4)	0.71565 (10)	0.31393 (16)	0.0173 (4)
H16	0.447058	0.709837	0.240584	0.021*
O1	0.6178 (3)	0.73370 (7)	0.52821 (11)	0.0198 (3)
O2	0.2995 (4)	0.65973 (8)	0.56960 (12)	0.0247 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0214 (3)	0.0199 (3)	0.0150 (3)	−0.00055 (19)	0.00235 (18)	0.00232 (18)
C2	0.0205 (10)	0.0179 (10)	0.0156 (9)	0.0036 (8)	0.0022 (7)	0.0008 (7)
N3	0.0211 (9)	0.0194 (9)	0.0166 (8)	−0.0004 (7)	0.0017 (7)	−0.0005 (7)
C3A	0.0209 (10)	0.0180 (10)	0.0203 (10)	0.0004 (8)	0.0033 (8)	−0.0002 (8)
C4	0.0265 (11)	0.0241 (11)	0.0175 (10)	−0.0013 (9)	0.0009 (8)	−0.0015 (8)
C5	0.0268 (11)	0.0234 (11)	0.0213 (11)	−0.0010 (9)	0.0017 (8)	−0.0048 (8)
C6	0.0212 (11)	0.0182 (10)	0.0300 (12)	−0.0016 (8)	0.0042 (9)	−0.0026 (9)
C7	0.0212 (10)	0.0180 (10)	0.0237 (11)	0.0006 (8)	0.0059 (8)	0.0014 (8)
C7A	0.0210 (10)	0.0180 (10)	0.0178 (10)	0.0034 (8)	0.0026 (8)	0.0011 (8)
C8	0.0190 (10)	0.0190 (10)	0.0142 (9)	0.0034 (8)	0.0002 (7)	−0.0005 (7)
C9	0.0207 (10)	0.0204 (10)	0.0149 (9)	0.0024 (8)	0.0021 (8)	−0.0003 (8)
C10	0.0200 (10)	0.0171 (10)	0.0153 (9)	0.0017 (8)	0.0026 (7)	0.0004 (7)
C11	0.0236 (11)	0.0206 (10)	0.0158 (9)	0.0034 (8)	−0.0005 (8)	−0.0034 (8)
C12	0.0217 (10)	0.0191 (10)	0.0214 (10)	0.0002 (8)	−0.0010 (8)	−0.0023 (8)
C13	0.0221 (10)	0.0193 (10)	0.0194 (10)	0.0017 (8)	0.0024 (8)	0.0013 (8)
C14	0.0229 (10)	0.0199 (10)	0.0145 (9)	0.0021 (8)	0.0012 (8)	0.0008 (8)
C15	0.0201 (10)	0.0169 (10)	0.0147 (10)	0.0027 (8)	−0.0004 (7)	0.0001 (7)
C16	0.0192 (10)	0.0197 (10)	0.0130 (9)	0.0026 (8)	0.0007 (7)	−0.0002 (7)
O1	0.0242 (8)	0.0227 (8)	0.0125 (7)	−0.0010 (6)	0.0010 (6)	0.0005 (6)
O2	0.0303 (8)	0.0281 (8)	0.0157 (7)	−0.0034 (7)	0.0030 (6)	0.0022 (6)

Geometric parameters (Å, º) top

S1—C7A	1.733 (2)	C10—C11	1.385 (3)
S1—C2	1.758 (2)	C10—C15	1.401 (3)
C2—N3	1.308 (3)	C11—C12	1.388 (3)
C2—C8	1.464 (3)	C12—C13	1.405 (3)
N3—C3A	1.380 (3)	C13—C14	1.377 (3)
C3A—C4	1.406 (3)	C14—C15	1.409 (3)
C3A—C7A	1.411 (3)	C15—C16	1.434 (3)
C4—C5	1.375 (3)	C4—H4	0.9500
C5—C6	1.407 (3)	C5—H5	0.9500
C6—C7	1.378 (3)	C6—H6	0.9500
C7—C7A	1.396 (3)	C7—H7	0.9500
C8—C16	1.357 (3)	C11—H11	0.9500
C8—C9	1.470 (3)	C12—H12	0.9500
C9—O2	1.210 (3)	C13—H13	0.9500
C9—O1	1.365 (3)	C14—H14	0.9500
C10—O1	1.379 (2)	C16—H16	0.9500

C7A—S1—C2	88.87 (10)	C14—C13—C12	120.1 (2)
N3—C2—C8	122.13 (19)	C13—C14—C15	120.63 (19)
N3—C2—S1	115.63 (16)	C10—C15—C14	117.67 (19)
C8—C2—S1	122.24 (15)	C10—C15—C16	118.07 (19)
C2—N3—C3A	110.75 (18)	C14—C15—C16	124.25 (19)
N3—C3A—C4	125.9 (2)	C8—C16—C15	121.26 (19)
N3—C3A—C7A	115.15 (19)	C9—O1—C10	122.61 (16)
C4—C3A—C7A	119.0 (2)	C5—C4—H4	120.5
C5—C4—C3A	119.1 (2)	C3A—C4—H4	120.5
C4—C5—C6	121.2 (2)	C4—C5—H5	119.4
C7—C6—C5	120.9 (2)	C6—C5—H5	119.4
C6—C7—C7A	118.1 (2)	C7—C6—H6	119.5
C7—C7A—C3A	121.7 (2)	C5—C6—H6	119.5
C7—C7A—S1	128.67 (17)	C6—C7—H7	121.0
C3A—C7A—S1	109.57 (16)	C7A—C7—H7	121.0
C16—C8—C2	121.80 (18)	C10—C11—H11	120.8
C16—C8—C9	119.64 (19)	C12—C11—H11	120.8
C2—C8—C9	118.56 (18)	C11—C12—H12	119.7
O2—C9—O1	116.96 (18)	C13—C12—H12	119.7
O2—C9—C8	125.2 (2)	C14—C13—H13	119.9
O1—C9—C8	117.81 (18)	C12—C13—H13	119.9
O1—C10—C11	116.83 (18)	C13—C14—H14	119.7
O1—C10—C15	120.59 (19)	C15—C14—H14	119.7
C11—C10—C15	122.58 (19)	C8—C16—H16	119.4
C10—C11—C12	118.41 (19)	C15—C16—H16	119.4
C11—C12—C13	120.6 (2)

C7A—S1—C2—N3	1.07 (17)	C16—C8—C9—O2	179.9 (2)
C7A—S1—C2—C8	−178.49 (18)	C2—C8—C9—O2	−0.2 (3)
C8—C2—N3—C3A	179.04 (18)	C16—C8—C9—O1	0.2 (3)
S1—C2—N3—C3A	−0.5 (2)	C2—C8—C9—O1	−179.90 (17)
C2—N3—C3A—C4	179.1 (2)	O1—C10—C11—C12	−178.97 (18)
C2—N3—C3A—C7A	−0.5 (3)	C15—C10—C11—C12	0.4 (3)
N3—C3A—C4—C5	−179.1 (2)	C10—C11—C12—C13	−0.9 (3)
C7A—C3A—C4—C5	0.5 (3)	C11—C12—C13—C14	0.7 (3)
C3A—C4—C5—C6	−1.1 (3)	C12—C13—C14—C15	0.1 (3)
C4—C5—C6—C7	0.6 (3)	O1—C10—C15—C14	179.76 (18)
C5—C6—C7—C7A	0.4 (3)	C11—C10—C15—C14	0.5 (3)
C6—C7—C7A—C3A	−1.0 (3)	O1—C10—C15—C16	−1.3 (3)
C6—C7—C7A—S1	177.72 (17)	C11—C10—C15—C16	179.42 (19)
N3—C3A—C7A—C7	−179.79 (19)	C13—C14—C15—C10	−0.7 (3)
C4—C3A—C7A—C7	0.6 (3)	C13—C14—C15—C16	−179.6 (2)
N3—C3A—C7A—S1	1.3 (2)	C2—C8—C16—C15	−179.62 (19)
C4—C3A—C7A—S1	−178.36 (16)	C9—C8—C16—C15	0.3 (3)
C2—S1—C7A—C7	179.9 (2)	C10—C15—C16—C8	0.2 (3)
C2—S1—C7A—C3A	−1.24 (16)	C14—C15—C16—C8	179.1 (2)
N3—C2—C8—C16	−5.4 (3)	O2—C9—O1—C10	179.04 (18)
S1—C2—C8—C16	174.10 (16)	C8—C9—O1—C10	−1.2 (3)
N3—C2—C8—C9	174.66 (19)	C11—C10—O1—C9	−178.83 (18)
S1—C2—C8—C9	−5.8 (3)	C15—C10—O1—C9	1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.95	2.46	3.383 (3)	163
C11—H11···N3ⁱⁱ	0.95	2.63	3.523 (3)	156
C13—H13···O2ⁱⁱⁱ	0.95	2.65	3.314 (3)	127

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

Acknowledgements

The authors acknowledge support by the Open Access Publication Funds of the Technical University of Braunschweig.

References

Azzam, R. A., Elboshi, H. A. & Elgemeie, G. H. (2020a). ACS Omega, 5, 30023–30036. Web of Science CrossRef CAS PubMed Google Scholar
Azzam, R. A., Elgemeie, G. H., Elsayed, R. E. & Jones, P. G. (2017a). Acta Cryst. E73, 1820–1822. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Elgemeie, G. H., Elsayed, R. E. & Jones, P. G. (2017b). Acta Cryst. E73, 1041–1043. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Elgemeie, G. H., Seif, M. M. & Jones, P. G. (2021). Acta Cryst. E77, 891–894. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Elsayed, R. E. & Elgemeie, G. H. (2020b). ACS Omega, 5, 26182–26194. Web of Science CrossRef CAS PubMed Google Scholar
Azzam, R. A., Osman, R. R. & Elgemeie, G. H. (2020c). ACS Omega, 5, 1640–1655. Web of Science CrossRef CAS PubMed Google Scholar
Bansal, Y., Sethi, P. & Bansal, G. (2013). Med. Chem. Res. 22, 3049–3060. Web of Science CrossRef CAS Google Scholar
Christie, R. M. & Lui, C. H. (2000). Dyes Pigments, 47, 79–89. CrossRef CAS Google Scholar
Curini, M., Cravotto, G., Epifano, F. & Giannone, G. (2006). Curr. Med. Chem. 13, 199–222. CrossRef PubMed CAS Google Scholar
Elgemeie, G. H. (1989). Chem. Ind. 19, 653–654. Google Scholar
Elgemeie, G. H., Ahmed, K. A., Ahmed, E. A., Helal, M. H. & Masoud, D. M. (2015). Pigm. Resin Technol. 44, 87–93. CrossRef CAS Google Scholar
Elgemeie, G. H. & Elghandour, A. H. (1990). Bull. Chem. Soc. Jpn, 63, 1230–1232. CrossRef CAS Google Scholar
Elgemeie, G. H., Shams, H. Z., Elkholy, Y. M. & Abbas, N. S. (2000a). Phosphorus Sulfur Silicon Relat. Elem. 165, 265–272. CrossRef CAS Google Scholar
Elgemeie, G. H., Shams, Z., Elkholy, Y. M. & Abbas, N. S. (2000b). Heterocycl. Commun. 6, 363–368. CrossRef CAS Google Scholar
Ezeh, V. C. & Harrop, T. C. (2012). Inorg. Chem. 51, 1213–1215. CrossRef CAS PubMed 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
Jasinski, J. P. & Paight, E. S. (1995). Acta Cryst. C51, 531–533. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kim, G.-J., Lee, K., Kwon, H. & Kim, H.-J. (2011). Org. Lett. 13, 2799–2801. CrossRef CAS PubMed Google Scholar
Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shi, D., Chen, S., Dong, B., Zhang, Y., Sheng, C., James, T. D. & Guo, Y. (2019). Chem. Sci. 10, 3715–3722. CrossRef CAS PubMed Google Scholar
Siemens (1994). XP. Siemens Analytical X–Ray Instruments, Madison, Wisconsin, USA. Google Scholar
Wang, H., Chen, G., Xu, X., Chen, H. & Ji, S. (2010). Dyes Pigments, 86, 238–248. Web of Science CrossRef CAS Google Scholar
Żamojć, K., Wiczk, W., Zaborowski, B., Jacewicz, D. & Chmurzyński, L. (2014). J. Fluoresc. 24, 713–718. PubMed 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.