research communications
d]thiazol-2-yl)-6-methyl-2H-chromen-2-one
of 3-(benzo[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-braunschweig.de
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.
The molecule of the title compound, C17H11NO2S, is almost planar, with an interplanar angle of 3.01 (3)° between the benzothiazole and chromene ring systems. A short intramolecular S⋯O=C contact of 2.727 (2) Å is observed. The crystal packing involves a layer structure parallel to (211), containing dimeric inversion-symmetric units connected by a `weak' C—H⋯O=C hydrogen bond.
Keywords: benzothiazole; coumarin; crystal structure.
CCDC reference: 2256779
1. Chemical context
Benzothiazole and its derivatives are important heterocyclic aromatic compounds. Benzothiazole can be readily substituted at the C-2 position of the thiazole ring (Elgemeie et al., 2020). Compounds containing a benzothiazolyl group have found numerous applications in medicine and in nonlinear optics (Sigmundová et al., 2007). Benzothiazole derivatives can also display strong fluorescence and luminescence in the solid state and in solution (Wang et al., 2010). Benzothiazole compounds as incorporated in organic light-emitting diodes have attracted substantial attention because of their notable photovoltaic properties (Ghanavatkar et al., 2020). Recently, we have synthesized novel heterocyclic derivatives involving the benzothiazole moiety, many of which showed significant biological and fluorescence activities (Azzam et al., 2020; Khedr et al., 2022).
Coumarin is a natural product with the H-chromen-2-one. Its derivatives represent an important class of organic heterocycles. Thus, they are constituents of many intensively investigated and commercially important organic fluorescent materials; they also display important biological activities and are found in synthetic drugs (Curini et al., 2006). Furthermore, many coumarin compounds are current photosensitizers with valuable applications in medicinal chemistry (Bansal et al., 2013). Because of their photochemical properties, coumarin compounds have found applications in nonlinear optical materials, solar energy collectors and charge-transfer agents (Kim et al., 2011), and also as daylight fluorescent pigments, tunable dye lasers, fluorescent probes and components of organic light-emitting diodes (Christie & Lui, 2000). The emission intensities of coumarin chromophores depend on the nature of their substituents at various sites (Żamojć et al., 2014).
2In two recent papers (Abdallah et al., 2022, 2023), we have given a more extensive list of references concerning the properties of benzothiazoles and including many of our own publications in these fields.
Some decades ago, we reported the syntheses and characterizations of novel coumarin derivatives that have found applications as laser dyes (Elgemeie, 1989); these included 3-(benzo[d]thiazol-2-yl)-2H-chromen-2-one, the desmethyl analogue of title compound 4, a benzothiazole-based coumarin derivative which was synthesized by the reaction of 2-(cyanomethyl)benzothiazole with salicyaldehyde. Afterwards, other research groups utilized essentially the same reaction to synthesize different derivatives of the same heterocyclic framework, including compound 4 (Chao et al., 2010; Makowska et al., 2019).
Recently, we attempted to synthesize N-[3-(benzo[d]thiazol-2-yl)-6-methyl-2-oxoquinolin-1(2H)-yl]benzamide (5) by the reaction of N-[2-(benzo[d]thiazol-2-yl)acetyl]benzohydrazide (1) (Azzam et al., 2021) with 5-methylsalicylaldehyde (2) (Fig. 1). However, the product gave a that was inconsistent with the proposed structure. Therefore, the X-ray was determined, indicating the formation of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one (4) as the sole product, presumably arising via the initial formation of adduct 3 and the subsequent elimination of benzohydrazide rather than water. This is consistent with our recent observation that the desmethyl compound mentioned above is also formed as an unintended product by an exactly analogous reaction (Abdallah et al., 2022). The products thus represent, by coincidence, a continuation of our research on developing new benzothiazole and coumarin derivatives as organic fluorescent constituents (Elgemeie et al., 2015).
2. Structural commentary
The structure of compound 4 is shown in Fig. 2. Its bond lengths and angles may be regarded as normal; a selection is presented in Table 1. The chromene and benzothiazole ring systems are planar as expected, with respective r.m.s. deviations of 0.020 and 0.015 Å; the angle between these planes is only 3.01 (3)°, so that the whole molecule almost planar. A short intramolecular S11⋯O2 contact of 2.792 (1) Å is observed. The desmethyl analogue (Abdallah et al., 2022) has, as expected, a closely similar molecular structure, with an S⋯O=C contact of 2.727 (2) Å and an interplanar angle of 6.47 (6)°, but is not isotypic to 4.
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3. Supramolecular features
The short contact H17⋯O2 (at −x + 2, −y, −z + 1; see Table 2) may be regarded as a `weak' hydrogen bond. It links the molecules to form inversion-symmetric dimers (Fig. 3) in which the S⋯S distance is 3.678 (1) Å. Adjacent dimers are related by translation to give an extended structure consisting of layers parallel to (211). The intercentroid distances (in Å) between rings of neighbouring layers, defining rings A–D as thiazole, the arene ring of benzothiazole, pyran and the arene ring of chromene, respectively, are A⋯C = 3.64, A⋯D = 3.70 and B⋯D = 3.61 [all with the symmetry code (−x + 1, −y + 1, −z + 1)], B⋯C = 3.51 and B⋯D = 3.66 Å [both with the symmetry code (−x + 2, −y + 1, −z + 1)]. The ring offsets (in the same order) are 1.44, 1.32, 0.80, 0.86 and 1.39 Å.
4. Database survey
The searches employed the routine ConQuest (Bruno et al., 2002), part of Version 2022.3.0 of the Cambridge Structural Database (Groom et al., 2016). A search for structures containing both a coumarin and a benzothiazole ring system in the same residue gave 16 hits. After excluding ring systems with more extended annelation and molecules where the ring systems were not directly bonded to each other, 7 hits remained. In all of these, the benzothiazole was bonded via its 2-position. The structure with refcode AKUCUG (Bakthadoss & Selvakumar, 2016) involved a linkage via the 8-position of the coumarin; the other 6 hits [VIVWEF and VIWDOX (Shi et al., 2019); WINZAU (Jasinski & Paight, 1995); SECSEC (Abdallah et al., 2022); PEGMEX and PEGMIB (Singh et al., 2022)] all had this linkage at the 3-position, as in compound 4. In all cases, a short intramolecular S⋯O=C contact was observed, with distances in the range 2.681–2.786 Å.
5. Synthesis and crystallization
5-Methylsalicylaldehyde, 2 (1.36 g, 0.01 mol) and ammonium acetate (0.77 g, 0.01 mol) were added to a solution of N-[2-(benzo[d]thiazol-2-yl)acetyl]benzohydrazide, 1 (3.11 g, 0.01 mol), in ethanol (10 mL). The reaction mixture was refluxed for ca 3 h and the resulting precipitate was collected by filtration and recrystallized from ethanol.
Pale-yellow crystals; yield: 96% (2.82 g); m.p. 495–497 K; IR (KBr, cm−1): ν 3062, (CH-aromatic), 2918 (CH3), 1710 (C=O), 1582 (C=N) and 1619, 1485 (C=C). 1H NMR (400 MHz, DMSO-d6): δ 2.40 (s, 3H, CH3), 7.42–8.18 (m, 7H, C6H4, C6H3), 9.19 (s, 1H, CH-pyran). 13C NMR (100 MHz, DMSO-d6): δ 20.8 (CH3), 116.5, 119.0, 120.0, 122.7, 123.0, 124.5, 125.9, 127.2, 128.6, 130.2, 135.2, 136.4, 142.4, 152.4 (aromatic C atoms, pyran ring), 160.0 (C=N), 160.4 (C=O). MS (EI): m/z (%) 293 [M+] (100.00). Analysis calculated (%) for C17H11NO2S: C 69.61, H 3.78, N 4.77, S 10.93; found: C 69.42, H 3.90, N 4.66, S 10.99.
6. Refinement
The title crystal was a non-merohedral two-component twin. The orientations are related by a 180° rotation around the reciprocal axis c*. The structure was refined using the HKLF5 method, whereby the relative volume of the smaller twin component refined to 0.387 (1). For non-merohedral twins thus refined, Rint is not a valid concept, and the number of reflections should be interpreted with caution, because the equivalent reflections in the intensity file have already been merged.
Crystal data, data collection and structure . The methyl group was included as an idealized rigid group allowed to rotate but not tip (C—H = 0.98 Å and H—C—H = 109.5°). Other H atoms were included using a riding model starting from calculated positions (aromatic C—H = 0.95 Å). The Uiso(H) values were fixed at 1.5 times Ueq of the parent C atoms for methyl groups and at 1.2 times Ueq for the other H atoms.
details are summarized in Table 3Supporting information
CCDC reference: 2256779
https://doi.org/10.1107/S205698902300347X/yz2033sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902300347X/yz2033Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2022); cell
CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).C17H11NO2S | Z = 2 |
Mr = 293.33 | F(000) = 304 |
Triclinic, P1 | Dx = 1.486 Mg m−3 |
a = 7.1592 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.0048 (2) Å | Cell parameters from 15669 reflections |
c = 10.8678 (3) Å | θ = 5.1–76.9° |
α = 82.779 (2)° | µ = 2.22 mm−1 |
β = 76.016 (2)° | T = 100 K |
γ = 75.078 (2)° | Lath, yellow |
V = 655.42 (3) Å3 | 0.2 × 0.08 × 0.03 mm |
Rigaku XtaLAB Synergy diffractometer | 4408 measured reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 4408 independent reflections |
Mirror monochromator | 4313 reflections with I > 2σ(I) |
Detector resolution: 10.0000 pixels mm-1 | θmax = 77.7°, θmin = 4.2° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2022) | k = −11→11 |
Tmin = 0.391, Tmax = 1.000 | l = −13→13 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.1477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
4408 reflections | Δρmax = 0.36 e Å−3 |
192 parameters | Δρmin = −0.28 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.51103 (16) | 0.48246 (12) | 0.81168 (9) | 0.0190 (2) | |
O2 | 0.6896 (2) | 0.26471 (13) | 0.73105 (10) | 0.0284 (3) | |
C2 | 0.6325 (2) | 0.40210 (18) | 0.71141 (13) | 0.0193 (3) | |
C3 | 0.6808 (2) | 0.48993 (17) | 0.58998 (12) | 0.0165 (3) | |
C4 | 0.6030 (2) | 0.64361 (17) | 0.57955 (12) | 0.0167 (3) | |
H4 | 0.632732 | 0.699040 | 0.499800 | 0.020* | |
C4A | 0.4771 (2) | 0.72457 (17) | 0.68581 (13) | 0.0163 (3) | |
C5 | 0.3967 (2) | 0.88415 (17) | 0.68151 (13) | 0.0180 (3) | |
H5 | 0.421660 | 0.943350 | 0.603163 | 0.022* | |
C6 | 0.2821 (2) | 0.95747 (18) | 0.78852 (13) | 0.0186 (3) | |
C7 | 0.2475 (2) | 0.86682 (17) | 0.90335 (13) | 0.0179 (3) | |
H7 | 0.169855 | 0.915469 | 0.977831 | 0.022* | |
C8A | 0.4369 (2) | 0.63944 (17) | 0.80150 (13) | 0.0163 (3) | |
C8 | 0.3231 (2) | 0.70939 (17) | 0.91095 (13) | 0.0185 (3) | |
H8 | 0.297826 | 0.650194 | 0.989268 | 0.022* | |
C9 | 0.1992 (3) | 1.12900 (19) | 0.78301 (15) | 0.0253 (3) | |
H9A | 0.109385 | 1.158236 | 0.864314 | 0.038* | |
H9B | 0.126469 | 1.159123 | 0.714667 | 0.038* | |
H9C | 0.307944 | 1.181373 | 0.766476 | 0.038* | |
S11 | 0.92276 (5) | 0.21156 (4) | 0.48745 (3) | 0.01826 (13) | |
C12 | 0.8130 (2) | 0.40930 (16) | 0.48039 (13) | 0.0163 (3) | |
N13 | 0.85618 (18) | 0.48415 (14) | 0.37018 (11) | 0.0170 (3) | |
C13A | 0.9840 (2) | 0.38535 (17) | 0.28225 (13) | 0.0167 (3) | |
C14 | 1.0636 (2) | 0.42978 (18) | 0.15610 (13) | 0.0189 (3) | |
H14 | 1.029684 | 0.533983 | 0.123985 | 0.023* | |
C15 | 1.1927 (2) | 0.31842 (18) | 0.07949 (13) | 0.0200 (3) | |
H15 | 1.249720 | 0.347072 | −0.005730 | 0.024* | |
C16 | 1.2408 (2) | 0.16354 (18) | 0.12571 (14) | 0.0205 (3) | |
H16 | 1.327948 | 0.089102 | 0.070564 | 0.025* | |
C17A | 1.0364 (2) | 0.23021 (17) | 0.32803 (13) | 0.0177 (3) | |
C17 | 1.1641 (2) | 0.11734 (18) | 0.24965 (14) | 0.0198 (3) | |
H17 | 1.196910 | 0.012568 | 0.280584 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0238 (6) | 0.0148 (5) | 0.0158 (5) | −0.0030 (4) | −0.0012 (4) | −0.0006 (4) |
O2 | 0.0399 (7) | 0.0162 (6) | 0.0212 (5) | −0.0006 (5) | 0.0006 (5) | 0.0007 (4) |
C2 | 0.0228 (7) | 0.0171 (7) | 0.0174 (6) | −0.0044 (6) | −0.0029 (5) | −0.0018 (5) |
C3 | 0.0178 (7) | 0.0169 (7) | 0.0151 (6) | −0.0046 (5) | −0.0036 (5) | −0.0016 (5) |
C4 | 0.0188 (7) | 0.0177 (7) | 0.0141 (6) | −0.0050 (6) | −0.0036 (5) | −0.0008 (5) |
C4A | 0.0165 (7) | 0.0178 (7) | 0.0153 (6) | −0.0044 (6) | −0.0037 (5) | −0.0021 (5) |
C5 | 0.0196 (7) | 0.0173 (7) | 0.0163 (6) | −0.0043 (6) | −0.0034 (5) | 0.0009 (5) |
C6 | 0.0179 (7) | 0.0181 (7) | 0.0198 (6) | −0.0034 (6) | −0.0046 (5) | −0.0024 (5) |
C7 | 0.0157 (7) | 0.0205 (7) | 0.0167 (6) | −0.0029 (5) | −0.0017 (5) | −0.0041 (5) |
C8A | 0.0170 (7) | 0.0149 (7) | 0.0174 (6) | −0.0047 (5) | −0.0039 (5) | −0.0004 (5) |
C8 | 0.0198 (7) | 0.0197 (7) | 0.0158 (6) | −0.0060 (6) | −0.0024 (5) | 0.0002 (5) |
C9 | 0.0317 (8) | 0.0180 (8) | 0.0217 (7) | −0.0002 (6) | −0.0027 (6) | −0.0034 (5) |
S11 | 0.0232 (2) | 0.01407 (19) | 0.01565 (19) | −0.00208 (14) | −0.00330 (13) | −0.00092 (13) |
C12 | 0.0172 (6) | 0.0160 (7) | 0.0162 (6) | −0.0040 (5) | −0.0046 (5) | −0.0011 (5) |
N13 | 0.0174 (6) | 0.0172 (6) | 0.0160 (5) | −0.0038 (5) | −0.0031 (4) | −0.0018 (4) |
C13A | 0.0157 (7) | 0.0168 (7) | 0.0180 (6) | −0.0038 (5) | −0.0037 (5) | −0.0027 (5) |
C14 | 0.0190 (7) | 0.0190 (7) | 0.0184 (6) | −0.0047 (6) | −0.0038 (5) | −0.0003 (5) |
C15 | 0.0186 (7) | 0.0240 (8) | 0.0175 (6) | −0.0067 (6) | −0.0017 (5) | −0.0028 (5) |
C16 | 0.0185 (7) | 0.0227 (8) | 0.0211 (7) | −0.0041 (6) | −0.0036 (5) | −0.0076 (6) |
C17A | 0.0186 (7) | 0.0171 (7) | 0.0186 (6) | −0.0052 (6) | −0.0051 (5) | −0.0016 (5) |
C17 | 0.0206 (7) | 0.0176 (7) | 0.0216 (7) | −0.0036 (6) | −0.0054 (5) | −0.0039 (5) |
O1—C2 | 1.3723 (17) | C13A—C14 | 1.4022 (19) |
O1—C8A | 1.3765 (18) | C13A—C17A | 1.409 (2) |
O2—C2 | 1.2077 (19) | C14—C15 | 1.383 (2) |
C2—C3 | 1.4645 (19) | C15—C16 | 1.406 (2) |
C3—C4 | 1.354 (2) | C16—C17 | 1.381 (2) |
C3—C12 | 1.4698 (19) | C17A—C17 | 1.399 (2) |
C4—C4A | 1.4310 (19) | C4—H4 | 0.9500 |
C4A—C8A | 1.3956 (19) | C5—H5 | 0.9500 |
C4A—C5 | 1.403 (2) | C7—H7 | 0.9500 |
C5—C6 | 1.384 (2) | C8—H8 | 0.9500 |
C6—C7 | 1.4083 (19) | C9—H9A | 0.9800 |
C6—C9 | 1.504 (2) | C9—H9B | 0.9800 |
C7—C8 | 1.381 (2) | C9—H9C | 0.9800 |
C8A—C8 | 1.3897 (19) | C14—H14 | 0.9500 |
S11—C17A | 1.7343 (14) | C15—H15 | 0.9500 |
S11—C12 | 1.7515 (15) | C16—H16 | 0.9500 |
C12—N13 | 1.3076 (18) | C17—H17 | 0.9500 |
N13—C13A | 1.3836 (18) | ||
C2—O1—C8A | 122.52 (11) | C14—C15—C16 | 121.07 (13) |
O2—C2—O1 | 116.99 (12) | C17—C16—C15 | 121.37 (14) |
O2—C2—C3 | 125.69 (14) | C17—C17A—C13A | 121.53 (13) |
O1—C2—C3 | 117.32 (13) | C17—C17A—S11 | 129.05 (12) |
C4—C3—C2 | 119.91 (13) | C13A—C17A—S11 | 109.42 (11) |
C4—C3—C12 | 120.78 (12) | C16—C17—C17A | 117.68 (14) |
C2—C3—C12 | 119.31 (13) | C3—C4—H4 | 119.2 |
C3—C4—C4A | 121.57 (12) | C4A—C4—H4 | 119.2 |
C8A—C4A—C5 | 118.28 (13) | C6—C5—H5 | 119.2 |
C8A—C4A—C4 | 117.62 (13) | C4A—C5—H5 | 119.2 |
C5—C4A—C4 | 124.07 (12) | C8—C7—H7 | 119.0 |
C6—C5—C4A | 121.65 (13) | C6—C7—H7 | 119.0 |
C5—C6—C7 | 117.94 (14) | C7—C8—H8 | 120.7 |
C5—C6—C9 | 121.11 (13) | C8A—C8—H8 | 120.7 |
C7—C6—C9 | 120.94 (13) | C6—C9—H9A | 109.5 |
C8—C7—C6 | 122.00 (13) | C6—C9—H9B | 109.5 |
O1—C8A—C8 | 117.40 (12) | H9A—C9—H9B | 109.5 |
O1—C8A—C4A | 121.01 (13) | C6—C9—H9C | 109.5 |
C8—C8A—C4A | 121.59 (14) | H9A—C9—H9C | 109.5 |
C7—C8—C8A | 118.53 (13) | H9B—C9—H9C | 109.5 |
C17A—S11—C12 | 88.94 (7) | C15—C14—H14 | 120.8 |
N13—C12—C3 | 120.72 (13) | C13A—C14—H14 | 120.8 |
N13—C12—S11 | 115.94 (11) | C14—C15—H15 | 119.5 |
C3—C12—S11 | 123.35 (10) | C16—C15—H15 | 119.5 |
C12—N13—C13A | 110.47 (12) | C17—C16—H16 | 119.3 |
N13—C13A—C14 | 124.90 (13) | C15—C16—H16 | 119.3 |
N13—C13A—C17A | 115.23 (12) | C16—C17—H17 | 121.2 |
C14—C13A—C17A | 119.86 (13) | C17A—C17—H17 | 121.2 |
C15—C14—C13A | 118.48 (14) | ||
C8A—O1—C2—O2 | 179.74 (13) | C4A—C8A—C8—C7 | 0.5 (2) |
C8A—O1—C2—C3 | −0.6 (2) | C4—C3—C12—N13 | −0.9 (2) |
O2—C2—C3—C4 | 178.35 (15) | C2—C3—C12—N13 | 178.82 (13) |
O1—C2—C3—C4 | −1.3 (2) | C4—C3—C12—S11 | 178.79 (11) |
O2—C2—C3—C12 | −1.3 (2) | C2—C3—C12—S11 | −1.53 (19) |
O1—C2—C3—C12 | 178.98 (12) | C17A—S11—C12—N13 | −0.22 (11) |
C2—C3—C4—C4A | 1.5 (2) | C17A—S11—C12—C3 | −179.88 (12) |
C12—C3—C4—C4A | −178.79 (13) | C3—C12—N13—C13A | 179.37 (12) |
C3—C4—C4A—C8A | 0.1 (2) | S11—C12—N13—C13A | −0.31 (15) |
C3—C4—C4A—C5 | 178.18 (13) | C12—N13—C13A—C14 | −178.01 (13) |
C8A—C4A—C5—C6 | 0.7 (2) | C12—N13—C13A—C17A | 0.85 (17) |
C4—C4A—C5—C6 | −177.38 (13) | N13—C13A—C14—C15 | 178.86 (13) |
C4A—C5—C6—C7 | 0.0 (2) | C17A—C13A—C14—C15 | 0.1 (2) |
C4A—C5—C6—C9 | 179.11 (13) | C13A—C14—C15—C16 | 1.1 (2) |
C5—C6—C7—C8 | −0.4 (2) | C14—C15—C16—C17 | −1.2 (2) |
C9—C6—C7—C8 | −179.54 (14) | N13—C13A—C17A—C17 | 179.81 (13) |
C2—O1—C8A—C8 | −177.01 (13) | C14—C13A—C17A—C17 | −1.3 (2) |
C2—O1—C8A—C4A | 2.3 (2) | N13—C13A—C17A—S11 | −1.00 (16) |
C5—C4A—C8A—O1 | 179.81 (12) | C14—C13A—C17A—S11 | 177.92 (11) |
C4—C4A—C8A—O1 | −2.0 (2) | C12—S11—C17A—C17 | 179.76 (15) |
C5—C4A—C8A—C8 | −1.0 (2) | C12—S11—C17A—C13A | 0.66 (11) |
C4—C4A—C8A—C8 | 177.23 (13) | C15—C16—C17—C17A | 0.0 (2) |
C6—C7—C8—C8A | 0.2 (2) | C13A—C17A—C17—C16 | 1.2 (2) |
O1—C8A—C8—C7 | 179.80 (12) | S11—C17A—C17—C16 | −177.78 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O2i | 0.95 | 2.43 | 3.3235 (19) | 157 |
Symmetry code: (i) −x+2, −y, −z+1. |
Acknowledgements
The authors acknowledge support by the Open Access Publication Funds of the Technical University of Braunschweig.
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