Synthesis and crystal structure of 2-(benzo[d]thia­zol-2-yl)-N′-[(E)-1-(4-bromo­phen­yl)ethyl­idene]acetohydrazide

Elboshi, H.A.; Azzam, R.A.; Elgemeie, G.H.; Jones, P.G.

doi:10.1107/S2056989026001313

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 82| Part 3| March 2026| Pages 293-296

https://doi.org/10.1107/S2056989026001313

Open

access

Synthesis and crystal structure of 2-(benzo[d]thiazol-2-yl)-N′-[(E)-1-(4-bromophenyl)ethylidene]acetohydrazide

Heba A. Elboshi,^a Rasha A. Azzam,^a Galal H. Elgemeie ^a and Peter G. Jones ^b ^*

^aChemistry Department, Faculty of Science, Capital University, Helwan, Egypt, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
^*Correspondence e-mail: [email protected]

Edited by C. Schulzke, Universität Greifswald, Germany (Received 27 January 2026; accepted 6 February 2026; online 24 February 2026)

The title compound (E)-2-(benzo[d]thiazol-2-yl)-N′-(1-(4-bromophenyl)ethylidene)acetohydrazide, C₁₇H₁₄BrN₃OS, crystallizes in space group P2₁/c with Z = 4. The configuration across the formal N=C double bond at the hydrazide moiety is E; the atom sequence C—C—C(= O)—N—N=C—(bromophenyl) is very approximately planar (r.m.s. deviation 0.17 Å, when all carbon atoms of the bromophenyl group are included), being synperiplanar around the C(=O)—N bond and antiperiplanar (choosing the appropriate final atom C_Ar) elsewhere. The interplanar angle to the benzothiazole unit (r.m.s. deviation 0.01 Å) is 69.75 (2)°. The main packing feature is a classical inversion-symmetric dimer with hydrogen bonds of the type N—H⋯O=C. This combines with a rather long N_thiazole⋯Br halogen bond to form a thick layer structure parallel to the bc plane.

Keywords: crystal structure; benzothiazole; hydrazide; hydrogen bond; halogen bond.

CCDC reference: 2529228

1. Chemical context

The benzothiazole scaffold is established as one of the most significant moieties in medicinal chemistry, because benzothiazole derivatives are present in a broad range of natural products and bioactive compounds, and many derivatives exhibit significant activity while causing few side-effects (Keri et al., 2015 ). Benzothiazole derivatives have attracted appreciable recent attention in medicinal chemistry because of their biological and pharmacological characteristics (Gill et al., 2015 ). Numerous biological activities, including anticancer, antifungal and antibacterial effects, are associated with the benzothiazole moiety; a more extensive description can be found in our previous publication (Elboshi et al., 2026 ) and references therein.

We have synthesised new heterocyclic compounds with incorporated benzothiazole motifs, and these too have demonstrated noteworthy biological activity (Azzam et al., 2017 ), e.g. benzothiazole-substituted coumarin residues, which also have useful optical characteristics (Abdallah et al., 2023 ). We have described some new coumarin compounds that are currently being used as laser dyes for medicinal applications (Elgemeie, 1989 ). We have also reported new benzothiazole-based heterocycles that showed significant fluorescence as well as biological importance (Azzam et al., 2022 ).

The goal of the current study was to design and produce benzothiazolyl ethylidene-acetohydrazides inspired by the results of our earlier work. The 2-(benzothiazolyl)-[1-(4-bromophenyl)ethylidene]acetohydrazide derivative 7 was synthesized in good yield by reacting 2-benzothiazolyl acetohydrazide 4 with 4-bromophenylacetophenone 5 in refluxing ethanol for 3 h (Fig. 1). The crystal structure of 7 was determined and is reported here.

Figure 1
The synthesis of compound 7.

2. Structural commentary

The molecule of compound 7 is shown in Fig. 2, with selected geometric parameters in Table 1. The molecular dimensions may be regarded as normal, e.g. the wide exocyclic angles at C3A and C7A. The configuration across the formal double bond N2=C10 is E, and this bond is some 0.06 Å shorter than the formal single bond N1—C9, although formal bond orders should be interpreted carefully in view of probable delocalization of the multiple bonding. The approximate synperiplanarity of the sequence C2—C8—C9—O1 is associated with the intramolecular S1⋯O1 contact of 3.1729 (10) Å, a feature that we have frequently observed in related compounds, generally with much shorter contact distances (e.g. Elboshi et al., 2026). As can be seen from the side view of the molecule in Fig. 3, the atom sequence C2–C8–C9–N1–N2–C10–C11–C12 is very approximately planar (r.m.s. deviation 0.17 Å, including the carbon atoms of the bromophenyl group), being synperiplanar around the bond C9—N1 and antiperiplanar elsewhere. The interplanar angle to the plane of the benzothiazole unit (r.m.s. deviation 0.01 Å) is 69.75 (2)°. The coordination geometry at the nitrogen atom N1 of the NH group is planar (r.m.s. deviation of 4 atoms 0.003 Å).

Table 1
Selected geometric parameters (Å, °)

S1—C7A	1.7342 (12)	C9—O1	1.2307 (15)
S1—C2	1.7507 (12)	C9—N1	1.3543 (15)
C2—N3	1.2976 (16)	N1—N2	1.3764 (15)
N3—C3A	1.3909 (16)	N2—C10	1.2942 (15)
C3A—C7A	1.4090 (17)

C7A—S1—C2	89.24 (6)	C7—C7A—S1	129.27 (10)
N3—C2—S1	115.90 (9)	C3A—C7A—S1	109.07 (8)
C2—N3—C3A	110.63 (10)	C9—N1—N2	119.49 (10)
N3—C3A—C4	125.01 (11)	C10—N2—N1	116.53 (10)
N3—C3A—C7A	115.16 (10)

N3—C2—C8—C9	−115.73 (13)	C9—N1—N2—C10	−179.12 (12)
C2—C8—C9—O1	−10.43 (19)	N1—N2—C10—C11	179.74 (11)
C2—C8—C9—N1	170.32 (12)	N2—C10—C11—C12	−160.60 (12)
C8—C9—N1—N2	−1.76 (18)

Figure 2
The molecule of compound 7 in the crystal. Ellipsoids correspond to 50% probability levels.

Figure 3
‘Side view' of the molecule of 7; hydrogen atoms are omitted and radii are arbitrary.

3. Supramolecular features

The NH group at N1 is involved in a classical hydrogen bond to O1 via an inversion centre (Table 2), leading to the well-known motif with graph set R₂²(8). Three borderline ‘weak' hydrogen bonds are also included in Table 2. There is a further contact N3⋯Br1 (x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z) of 3.1572 (10) Å, with an N⋯Br—C angle of 161.26 (4)°, that may be regarded as a ‘halogen bond' [for reviews of this topic, see e.g. Cavallo et al. (2016 ) or Metrangolo et al. (2008 )]. The combination of classical hydrogen bond plus halogen bond leads to the formation of a layer structure (Fig. 4) parallel to the bc plane and with a thickness equal to the length of the a axis. Because the hydrogen bonds are seen almost end-on in Fig. 4, a projection of the structure parallel to the b axis (Fig. 5) is also shown for the sake of clarity.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯O1ⁱ	0.91 (2)	1.98 (2)	2.8839 (14)	168 (2)
C7—H7⋯N3ⁱⁱ	0.95	2.68	3.5942 (17)	161
C17—H11B⋯Br1ⁱⁱⁱ	0.98	2.93	3.7666 (12)	145
C17—H11C⋯N2^iv	0.98	2.69	3.5464 (18)	147
Symmetry codes: (i) ; (ii) ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) .

Figure 4
Packing diagram of compound 7: One layer viewed perpendicular to the bc plane, showing classical hydrogen bonds (seen almost end-on, cf. Fig. 5

) and halogen bonds (both as thick dashed lines). Hydrogen atoms not involved in the hydrogen bonding are omitted. Labels indicate atoms of the asymmetric unit.

Figure 5
Simplified packing diagram of compound 7 shown as a projection parallel to the b axis.

4. Database survey

Searches were conducted using CSD Version 6.00 (update August 2025; Groom et al., 2016 ) and the ConQuest routine (Bruno et al., 2002 ), Version 2025.2.0. The main search was based on the standard benzo[d]thiazole ring system with appropriately defined coordination numbers but no limitations on bond orders or on substituents except for that at C2; this substituent was set to –C⁴–C³(–O¹)–N^any (as in 7), where the superscripts indicate coordination number, whereby all bond orders in this fragment were allowed. This gave 18 hits. Only three of these structures had a 2-substituent of the type –C⁴–C³(–O¹)–N^any–N^any (as in 7): 4-(1,3-benzothiazol-2-yl)-5-methyl-2-phenyl-4-(prop-2-en-1-yl)-2,4-dihydro-3H-pyrazol-3-one (refcode DOMYAI: Chakib et al., 2019 ) and our previous structures, the hydrazine derivatives N′-[(1,3-benzothiazol-2-yl)acetyl]benzohydrazide (IYUSIH; Azzam et al., 2021 ) and 2-(1,3-benzothiazol-2-yl)-N′-[(4-methylphenyl)sulfonyl]acetohydrazide (JEBQOZ; Azzam et al., 2017). Similarly, only three structures involved the 2-substituent –CH₂–C³(–O¹)–N^any (as in 7), namely IYUSIH, JEBQOZ and 2-(1,3-benzothiazol-2-yl)-N-(2-hydroxyphenyl)acetamide (HANREW; Dauer et al., 2017 ).

5. Synthesis and crystallization

A mixture of 2-benzothiazolyl acetohydrazide 4 (2.072 g, 0.01 mol) and 4-bromophenylacetophenone 5 (3.98 g, 0.02 mol) was refluxed in ethanol (30 mL) for 3 h. The colourless solid product 7 thus formed was filtered from the hot solution, washed with a mixture of petroleum ether and ethyl acetate (1:1) and then recrystallized from ethanol.

Yellow solid; yield 80%; m.p. 466–468 K. IR (KBr, cm⁻¹): ν 3182 (NH), 3054 (Ar—CH), 1669 (CO); ¹H NMR (400 MHz, DMSO-d₆): δ 2.22 (s, 3H, CH₃), 4.36 (s, 2H, CH₂), 7.38–7.62 (m, 4H, Ar-H & benzothiazole-H), 7.74 (d, J = 8.4, 2H, Ar-H), 7.96 (d, J = 8.0 Hz, 1H, benzothiazole-H), 8.04 (d, J = 7.6 Hz, 1H, benzothiazole-H), 10.90 (s, 1H, NH). Analysis: calculated for C₁₇H₁₄BrN₃OS (388.28): C 52.59, H 3.63, N 10.82. Found: C 52.53, H 3.60, N 10.81%.

6. Refinement

Details of data collection and structure refinement are summarized in Table 3. The benzothiazole system was assigned the standard IUPAC numbering. The hydrogen atom of the NH group was refined freely. The methyl group was refined as an idealized rigid group with C—H = 0.98 Å, H—C—H = 109.5°, allowed to rotate but not tip (AFIX 137). Other hydrogen atoms were included using a riding model starting from calculated positions (C—H_arom = 0.95, C—H_methylene = 0.98 Å). The U(H) values were fixed at 1.5 × U_eq of the parent carbon atoms for the methyl group and 1.2 × U_eq for the other hydrogens.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₇H₁₄BrN₃OS
M_r	388.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.4768 (3), 6.73234 (16), 17.8734 (5)
β (°)	98.169 (2)
V (Å³)	1605.21 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.70
Crystal size (mm)	0.25 × 0.10 × 0.04

Data collection
Diffractometer	XtaLAB Synergy
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2024 )
T_min, T_max	0.563, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	143532, 8606, 7894
R_int	0.063
θ values (°)	θ_max = 37.8, θ_min = 2.3
(sin θ/λ)_max (Å⁻¹)	0.862

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.085, 1.18
No. of reflections	8606
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.44, −0.71
Computer programs: CrysAlis PRO (Rigaku OD, 2024), SHELXT (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), XP (Bruker, 1998 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2529228

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989026001313/yz2073sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026001313/yz2073Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026001313/yz2073Isup3.cml

checkCIF report

Computing details top

2-(Benzo[d]thiazol-2-yl)-N'-[(E)-1-(4-bromophenyl)ethylidene]acetohydrazide top

Crystal data top

C₁₇H₁₄BrN₃OS	F(000) = 784
M_r = 388.28	D_x = 1.607 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.4768 (3) Å	Cell parameters from 56121 reflections
b = 6.73234 (16) Å	θ = 2.3–43.5°
c = 17.8734 (5) Å	µ = 2.70 mm⁻¹
β = 98.169 (2)°	T = 100 K
V = 1605.21 (7) Å³	Lath, colourless
Z = 4	0.25 × 0.10 × 0.04 mm

Data collection top

XtaLAB Synergy diffractometer	8606 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	7894 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.063
Detector resolution: 10.0000 pixels mm^-1	θ_max = 37.8°, θ_min = 2.3°
ω scans	h = −23→23
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2024)	k = −11→11
T_min = 0.563, T_max = 1.000	l = −30→30
143532 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0311P)² + 1.1712P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.001
8606 reflections	Δρ_max = 1.44 e Å⁻³
213 parameters	Δρ_min = −0.71 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.16962 (2)	1.25918 (5)	0.49911 (2)	0.01614 (6)
C2	0.17813 (8)	1.00142 (18)	0.51133 (7)	0.01334 (18)
N3	0.12596 (8)	0.92656 (15)	0.56014 (6)	0.01357 (16)
C3A	0.07440 (8)	1.07504 (17)	0.59266 (7)	0.01226 (17)
C4	0.01259 (9)	1.0444 (2)	0.64826 (7)	0.0167 (2)
H4	0.003219	0.914827	0.667136	0.020*
C5	−0.03465 (10)	1.2067 (2)	0.67519 (8)	0.0185 (2)
H5	−0.076718	1.188063	0.712990	0.022*
C6	−0.02120 (9)	1.3985 (2)	0.64740 (8)	0.0176 (2)
H6	−0.055025	1.507238	0.666381	0.021*
C7	0.04045 (9)	1.43262 (19)	0.59281 (7)	0.0156 (2)
H7	0.049896	1.562658	0.574429	0.019*
C7A	0.08812 (8)	1.26853 (17)	0.56588 (7)	0.01244 (17)
C8	0.23962 (9)	0.8749 (2)	0.46650 (8)	0.0168 (2)
H8A	0.217578	0.898276	0.411983	0.020*
H8B	0.227229	0.733355	0.477020	0.020*
C9	0.35099 (8)	0.91582 (18)	0.48404 (7)	0.01371 (18)
O1	0.38489 (7)	1.05873 (16)	0.52236 (7)	0.0214 (2)
N1	0.41315 (8)	0.78849 (16)	0.45479 (7)	0.01472 (17)
H01	0.4799 (18)	0.818 (3)	0.4639 (13)	0.028 (6)*
N2	0.37355 (8)	0.62797 (16)	0.41312 (6)	0.01411 (17)
C10	0.43690 (9)	0.51041 (18)	0.38756 (7)	0.01316 (18)
C11	0.39222 (9)	0.33802 (17)	0.34310 (7)	0.01298 (18)
C12	0.44925 (9)	0.17000 (18)	0.33140 (7)	0.01525 (19)
H13	0.517977	0.165244	0.352572	0.018*
C13	0.40666 (9)	0.00945 (19)	0.28910 (7)	0.0158 (2)
H14	0.445809	−0.104428	0.281831	0.019*
C14	0.30657 (9)	0.01796 (18)	0.25778 (7)	0.01412 (18)
Br1	0.24979 (2)	−0.19335 (2)	0.19566 (2)	0.01864 (4)
C15	0.24758 (9)	0.1824 (2)	0.26853 (8)	0.0181 (2)
H16	0.179047	0.186459	0.246826	0.022*
C16	0.29056 (9)	0.34051 (19)	0.31154 (8)	0.0171 (2)
H17	0.250470	0.452312	0.319744	0.021*
C17	0.54844 (9)	0.5433 (2)	0.40014 (8)	0.0166 (2)
H11A	0.564414	0.664090	0.373666	0.025*
H11B	0.582002	0.429331	0.380591	0.025*
H11C	0.571579	0.557948	0.454370	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01733 (12)	0.01212 (11)	0.02066 (14)	0.00074 (9)	0.00852 (10)	0.00166 (10)
C2	0.0104 (4)	0.0123 (4)	0.0171 (5)	0.0004 (3)	0.0012 (3)	−0.0023 (4)
N3	0.0124 (4)	0.0112 (4)	0.0167 (4)	0.0010 (3)	0.0007 (3)	0.0009 (3)
C3A	0.0112 (4)	0.0119 (4)	0.0133 (4)	0.0005 (3)	0.0005 (3)	0.0013 (3)
C4	0.0156 (4)	0.0188 (5)	0.0161 (5)	−0.0014 (4)	0.0032 (4)	0.0030 (4)
C5	0.0149 (4)	0.0250 (6)	0.0162 (5)	−0.0006 (4)	0.0048 (4)	−0.0010 (5)
C6	0.0142 (4)	0.0208 (5)	0.0178 (5)	0.0029 (4)	0.0025 (4)	−0.0036 (4)
C7	0.0155 (4)	0.0131 (4)	0.0181 (5)	0.0030 (4)	0.0022 (4)	−0.0011 (4)
C7A	0.0116 (4)	0.0113 (4)	0.0145 (5)	0.0010 (3)	0.0022 (3)	0.0005 (3)
C8	0.0114 (4)	0.0165 (5)	0.0226 (6)	−0.0001 (4)	0.0021 (4)	−0.0074 (4)
C9	0.0111 (4)	0.0137 (4)	0.0163 (5)	0.0006 (3)	0.0018 (3)	−0.0037 (4)
O1	0.0125 (3)	0.0209 (4)	0.0306 (5)	−0.0009 (3)	0.0026 (3)	−0.0145 (4)
N1	0.0116 (4)	0.0138 (4)	0.0191 (5)	−0.0003 (3)	0.0031 (3)	−0.0059 (3)
N2	0.0135 (4)	0.0134 (4)	0.0156 (4)	−0.0002 (3)	0.0024 (3)	−0.0038 (3)
C10	0.0131 (4)	0.0133 (4)	0.0132 (4)	0.0003 (3)	0.0026 (3)	−0.0025 (4)
C11	0.0136 (4)	0.0126 (4)	0.0129 (4)	0.0001 (3)	0.0026 (3)	−0.0021 (3)
C12	0.0145 (4)	0.0143 (5)	0.0164 (5)	0.0021 (3)	0.0000 (4)	−0.0032 (4)
C13	0.0165 (4)	0.0133 (4)	0.0171 (5)	0.0019 (4)	0.0012 (4)	−0.0031 (4)
C14	0.0159 (4)	0.0130 (4)	0.0140 (5)	−0.0026 (3)	0.0036 (4)	−0.0029 (4)
Br1	0.01679 (5)	0.01735 (6)	0.02281 (7)	−0.00640 (4)	0.00638 (4)	−0.00819 (5)
C15	0.0133 (4)	0.0176 (5)	0.0228 (6)	−0.0006 (4)	0.0006 (4)	−0.0050 (4)
C16	0.0134 (4)	0.0151 (5)	0.0225 (6)	0.0013 (4)	0.0015 (4)	−0.0053 (4)
C17	0.0126 (4)	0.0186 (5)	0.0187 (5)	−0.0004 (4)	0.0027 (4)	−0.0068 (4)

Geometric parameters (Å, º) top

S1—C7A	1.7342 (12)	C12—C13	1.3950 (17)
S1—C2	1.7507 (12)	C13—C14	1.3862 (17)
C2—N3	1.2976 (16)	C14—C15	1.3919 (18)
C2—C8	1.4977 (17)	C14—Br1	1.8975 (12)
N3—C3A	1.3909 (16)	C15—C16	1.3905 (18)
C3A—C4	1.3998 (17)	C4—H4	0.9500
C3A—C7A	1.4090 (17)	C5—H5	0.9500
C4—C5	1.385 (2)	C6—H6	0.9500
C5—C6	1.405 (2)	C7—H7	0.9500
C6—C7	1.3875 (19)	C8—H8A	0.9900
C7—C7A	1.3973 (17)	C8—H8B	0.9900
C8—C9	1.5144 (16)	N1—H01	0.91 (2)
C9—O1	1.2307 (15)	C12—H13	0.9500
C9—N1	1.3543 (15)	C13—H14	0.9500
N1—N2	1.3764 (15)	C15—H16	0.9500
N2—C10	1.2942 (15)	C16—H17	0.9500
C10—C11	1.4849 (17)	C17—H11A	0.9800
C10—C17	1.5044 (17)	C17—H11B	0.9800
C11—C12	1.3999 (17)	C17—H11C	0.9800
C11—C16	1.4057 (17)

C7A—S1—C2	89.24 (6)	C16—C15—C14	118.95 (11)
N3—C2—C8	122.18 (11)	C15—C16—C11	121.23 (11)
N3—C2—S1	115.90 (9)	C5—C4—H4	120.7
C8—C2—S1	121.90 (9)	C3A—C4—H4	120.7
C2—N3—C3A	110.63 (10)	C4—C5—H5	119.5
N3—C3A—C4	125.01 (11)	C6—C5—H5	119.5
N3—C3A—C7A	115.16 (10)	C7—C6—H6	119.3
C4—C3A—C7A	119.84 (11)	C5—C6—H6	119.3
C5—C4—C3A	118.66 (12)	C6—C7—H7	121.2
C4—C5—C6	120.91 (12)	C7A—C7—H7	121.2
C7—C6—C5	121.40 (12)	C2—C8—H8A	108.9
C6—C7—C7A	117.51 (12)	C9—C8—H8A	108.9
C7—C7A—C3A	121.67 (11)	C2—C8—H8B	108.9
C7—C7A—S1	129.27 (10)	C9—C8—H8B	108.9
C3A—C7A—S1	109.07 (8)	H8A—C8—H8B	107.8
C2—C8—C9	113.15 (10)	C9—N1—H01	116.1 (15)
O1—C9—N1	120.57 (11)	N2—N1—H01	124.4 (15)
O1—C9—C8	122.41 (11)	C13—C12—H13	119.5
N1—C9—C8	117.01 (10)	C11—C12—H13	119.5
C9—N1—N2	119.49 (10)	C14—C13—H14	120.4
C10—N2—N1	116.53 (10)	C12—C13—H14	120.4
N2—C10—C11	115.41 (10)	C16—C15—H16	120.5
N2—C10—C17	123.54 (11)	C14—C15—H16	120.5
C11—C10—C17	121.04 (10)	C15—C16—H17	119.4
C12—C11—C16	118.30 (11)	C11—C16—H17	119.4
C12—C11—C10	121.47 (10)	C10—C17—H11A	109.5
C16—C11—C10	120.23 (10)	C10—C17—H11B	109.5
C13—C12—C11	120.98 (11)	H11A—C17—H11B	109.5
C14—C13—C12	119.25 (11)	C10—C17—H11C	109.5
C13—C14—C15	121.28 (11)	H11A—C17—H11C	109.5
C13—C14—Br1	119.58 (9)	H11B—C17—H11C	109.5
C15—C14—Br1	119.09 (9)

C7A—S1—C2—N3	−0.02 (10)	C2—C8—C9—O1	−10.43 (19)
C7A—S1—C2—C8	178.31 (10)	C2—C8—C9—N1	170.32 (12)
C8—C2—N3—C3A	−178.76 (11)	O1—C9—N1—N2	178.97 (12)
S1—C2—N3—C3A	−0.44 (13)	C8—C9—N1—N2	−1.76 (18)
C2—N3—C3A—C4	−178.97 (12)	C9—N1—N2—C10	−179.12 (12)
C2—N3—C3A—C7A	0.82 (14)	N1—N2—C10—C11	179.74 (11)
N3—C3A—C4—C5	−179.62 (12)	N1—N2—C10—C17	−1.04 (19)
C7A—C3A—C4—C5	0.60 (18)	N2—C10—C11—C12	−160.60 (12)
C3A—C4—C5—C6	0.1 (2)	C17—C10—C11—C12	20.16 (18)
C4—C5—C6—C7	−0.7 (2)	N2—C10—C11—C16	19.43 (18)
C5—C6—C7—C7A	0.57 (19)	C17—C10—C11—C16	−159.82 (12)
C6—C7—C7A—C3A	0.15 (18)	C16—C11—C12—C13	0.41 (19)
C6—C7—C7A—S1	−179.52 (10)	C10—C11—C12—C13	−179.56 (12)
N3—C3A—C7A—C7	179.45 (11)	C11—C12—C13—C14	0.6 (2)
C4—C3A—C7A—C7	−0.75 (18)	C12—C13—C14—C15	−0.8 (2)
N3—C3A—C7A—S1	−0.82 (13)	C12—C13—C14—Br1	176.63 (10)
C4—C3A—C7A—S1	178.98 (9)	C13—C14—C15—C16	0.1 (2)
C2—S1—C7A—C7	−179.84 (12)	Br1—C14—C15—C16	−177.39 (11)
C2—S1—C7A—C3A	0.46 (9)	C14—C15—C16—C11	1.0 (2)
N3—C2—C8—C9	−115.73 (13)	C12—C11—C16—C15	−1.2 (2)
S1—C2—C8—C9	66.05 (14)	C10—C11—C16—C15	178.79 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1ⁱ	0.91 (2)	1.98 (2)	2.8839 (14)	168 (2)
C7—H7···N3ⁱⁱ	0.95	2.68	3.5942 (17)	161
C17—H11B···Br1ⁱⁱⁱ	0.98	2.93	3.7666 (12)	145
C17—H11C···N2^iv	0.98	2.69	3.5464 (18)	147

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

Acknowledgements

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

References

Abdallah, A. E. M., Abdel-Latif, S. A. & Elgemeie, G. H. (2023). ACS Omega 8, 19587–19602. Web of Science CrossRef PubMed 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., Seif, M. M. & Jones, P. G. (2021). Acta Cryst. E77, 891–894. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Gad, N. M. & Elgemeie, G. H. (2022). ACS Omega 7, 35656–35667. CrossRef PubMed Google Scholar
Bruker (1998). XP. Bruker Analytical X–Ray Instruments, Madison, Wisconsin, USA. 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
Cavallo, G., Metrangolo, P., Milani, R., Pilati, T., Priimagi, A., Resnati, G. & Terraneo, G. (2016). Chem. Rev. 116, 2478–2601. Web of Science CrossRef CAS PubMed Google Scholar
Chakib, I., El Bakri, Y., Lai, C.-H., Benbacer, L., Zerzouf, A., Essassi, E. M. & Mague, J. T. (2019). J. Mol. Struct. 1198, 126910. CrossRef Google Scholar
Dauer, D.-R., Koehne, I., Herbst-Irmer, R. & Stalke, D. (2017). Eur. J. Inorg. Chem. pp. 1966–1978. Web of Science CSD CrossRef Google Scholar
Elboshi, H. A., Azzam, R. A., Elgemeie, G. H. & Jones, P. G. (2026). Acta Cryst. E82, 182–186. CrossRef IUCr Journals Google Scholar
Elgemeie, G. H. (1989). Chem. Ind. 19, 653–654. Google Scholar
Gill, R. K., Rawal, R. K. & Bariwal, J. (2015). Arch. Pharm. 348, 155–178. Web of Science CrossRef CAS 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
Keri, R. S., Patil, M. R., Patil, S. A. & Budagumpi, S. (2015). Eur. J. Med. Chem. 89, 207–251. Web of Science CrossRef CAS PubMed Google Scholar
Metrangolo, P., Meyer, F., Pilati, T., Resnati, G. & Terraneo, G. (2008). Angew. Chem. Int. Ed. 47, 6114–6127. Web of Science CrossRef CAS Google Scholar
Rigaku OD. (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals 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.