research communications
Different patterns of supramolecular aggregation in three N-(benzo[d]thiazolyl) substituents
containingaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, India, cInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
Crystal structures are reported for three N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br⋯Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.
containing1. Chemical context
Compounds containing the benzo[d]thiazole unit exhibit a wide range of biological and medicinal activities, which have been reviewed by Henary et al. (2013). Notable examples include the presence of the benzo[d]thiazole nucleus in firefly luciferin, (4S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid (White et al., 1963), action as potent and selective human adenosine A3 receptor antagonists (Jung et al., 2004) and cholinesterase inhibitors (Imramovský et al., 2013). In addition, applications in Green Chemistry have very recently been reviewed (Gao et al., 2020).
Against this diverse background, we report here the synthesis and structures of three d]thiazole nucleus, namely: N-(benzo[d]thiazol-6-yl)-3-bromobenzamide (I), N-(6-methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide (II) and N-(6-methoxybenzo[d]thiazol-2-yl)-5-cyclopropylisoxazole-3-carboxamide (III). Compounds (I)–(III) were prepared in yields exceeding 85% by the reaction of an amino-substituted benzo[d]thiazole with an acid chloride in the presence of triethylamine.
containing the benzo[2. Structural commentary
In compound (I), the amide unit occupies position 6 of the benzo[d]thiazole unit, whereas in compounds (II) and (III), the amide unit is linked to the bicyclic system at position 2. In (I), (Fig. 1) the thiazole ring and the brominated aryl ring are almost parallel, with a dihedral angle between them of 5.8 (2)°. However, these rings are not coplanar, as both ring systems in compound (I) are twisted out of the plane of the central amide spacer unit.
Compound (II) crystallizes with Z′ = 2, but a search for possible additional revealed none. The different conformations of the two independent molecules (Fig. 2) confirm the absence of additional symmetry. For example, the dihedral angle between the thiazole ring and the nitrated phenyl ring is 46.43 (15)° in molecule 1 containing atom S111, but 66.35 (13)° in molecule 2 containing atom S211. Similarly, the dihedral angles between the nitro groups and the adjacent aryl rings are 34.5 (2) and 17.9 (2)° in molecules 1 and 2, respectively.
The molecule of compound (III) exhibits two forms of disorder. The cyclopropylisoxazole unit is disordered over two sets of atomic sites, with occupancies 0.549 (5) and 0.451 (5), where the two orientations of the isoxazole ring are approximately related by small rotations about the N—C and C—C bonds involving atom C31 (Fig. 3). Of more interest is the disorder of the methoxy groups, where the site occupancies are constrained by short non-bonded contacts with adjacent molecules. Thus, the atomic site C18 in the molecule at (x, y, z) is only 1.840 (8) Å from the corresponding site in the molecule at (2 − x, y, 1.5 − z): hence, only one of these sites can be occupied and this, in turn, limits this site occupancy in each molecule to a maximum value of 0.5. Similarly, the atomic site C19 at (x, y, z) is only 1.921 (9) Å from the corresponding site in the molecule at (2 − x, 1 − y, 1 − z), again limiting the site occupancy to a maximum value of 0.5. Hence the site occupancy for each orientation of the methoxy group must each be exactly 0.5.
In each of the independent methoxy groups in compound (II), and for each orientation of the methoxy group in compound (III), the two exocyclic C—C—O angles differ by ca 10%, as is generally found in planar, or nearly planar, alkoxyarenes (Seip & Seip, 1973; Ferguson et al., 1996). In compounds (II) and (III), the maximum displacement of any methoxy C atoms from the plane of the adjacent aryl ring is 0.144 (9) Å for atom C218 in compound (II).
3. Supramolecular features
The supramolecular assembly of compound (I) is built up from N—H⋯O and C—H⋯N hydrogen bonds (Table 1). Molecules related by translation are linked by N—H⋯O hydrogen bonds to form a C(4) (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995) chain, of the type very commonly found in simple (Fun et al., 2011a,b; Praveen et al., 2011; Fun, Quah et al., 2012; Fun, Shahani et al., 2012; Praveen et al., 2013a,b; Nayak et al., 2014): in (I), this chain runs parallel to the [010] direction (Fig. 4). In addition, molecules that are related by the 21 screw axis along (0.5, y, 0.25) are linked by C—H⋯N hydrogen bonds to form a C(6) chain, also running parallel to the [010] direction. The combination of these two chain motifs generates a ribbon of R33(19) rings along [010] (Fig. 4). Also running through the is a second ribbon of this type, related to the first by inversion, and containing molecules that are related by the 21 screw axis along (0.5, y, 0.75). Also present in the structure of compound (I) are two intermolecular Br⋯Br contacts that are shorter than the van der Waals radii sum of 3.74 Å (Rowland & Taylor, 1996). Atom Br3 in the molecule at (x, y, z) makes contacts with the corresponding atoms at (2 − x, 0.5 + y, 1.5 − z) and (2 − x, −0.5 + y, 1.5 − z), with Br⋯Br distances of 3.5812 (6) Å in each case; however, the C—Br⋯Br angles are 92.64 (18) and 166.44 (10)°, respectively (Fig. 5), which are consistent with the angular preferences found for such contacts from database analyses (Ramasubbu et al., 1986). The effects of these halogen bonds (Cavallo et al., 2016) are twofold: firstly to generate a chain running parallel to the [010] direction (Fig. 5) and thence to link the hydrogen-bonded ribbons into sheets lying parallel to the (10) plane (Fig. 6).
The two independent molecules of compound (II) are linked by two N—H⋯N hydrogen bonds and five C—H⋯O hydrogen bonds (Table 1), but the N—H⋯O hydrogen bonds typical of are absent. The hydrogen bonds generate a three-dimensional network, whose formation can readily be analysed in terms of a number of simple sub-structures (Ferguson et al., 1998a,b; Gregson et al., 2000). In the simplest of the sub-structures, the two N—H⋯N hydrogen bonds link the molecules within the selected to form a dimer, and the other sub-structures follow the different ways in which these dimers can be linked. The C—H⋯O hydrogen bonds involving atoms C25 and C115 link the dimers into a chain of alternating R22(8) R33(18) rings running parallel to the [001] direction (Fig. 7); this chain is weakly reinforced by a C—H⋯π(arene) interaction (Table 1). In the third sub-structure, the C—H⋯O hydrogen bonds involving atoms C13 and C217 link the dimers into a chain of rings containing C44(24) chains and running parallel to the [010] direction (Fig. 8). The combination of the chains along [010] and [001] generates a sheet lying parallel to (100) in the domain 0.5 < x < 1.0. A second sheet of the type, related to the first by the 21 screw axes, lies in the domain 0 < x < 0.5, and sheets of this type are linked by the C—H⋯O hydrogen bond in involving atom C117, so forming a three-dimensional network: indeed, it is possible to identify a complex chain running parallel to the [100] direction, which defines the linkage of the (100) sheets (Fig. 9).
Analysis of the supramolecular aggregation in compound (III) is complicated by the disorder of the isoxazole ring, since atoms O1A and N2A in the major disorder form act as hydrogen bond acceptors, but atoms O1B and N2B in the minor disorder form do not. As in (II), the N—H⋯O hydrogen bonds typical of are absent from the structure of (III). Molecules of (III) that are related by a twofold rotation axis are linked into cyclic R22(8) dimers. There is also present an asymmetric three-centre C—H⋯(N,O) system having atoms O1A and N2A as the acceptors: if these sites had full occupancy, this interaction would generate a chain of rings running parallel to the [101] direction (Fig. 10). However, because of the disorder, this chain is punctuated rather than continuous.
4. Database survey
N-(Benzo[d]thiazol-2-yl)-3-bromobenzamide (IV) [CSD (Groom et al., 2016) refcode SUQTAC; Odame et al., 2020] is a positional isomer of compound (I), with the amide substituent as position 2 of the benzothiazole unit, rather than at position 6 as in (I). In contrast to compound (I), but consistent with compounds (II) and (III), where the amide units are also linked to the heterocycle at position 6, the structure of (IV) contains no N—H⋯O hydrogen bonds: instead, inversion-related pairs of molecules are linked by pairwise N—H⋯N hydrogen bonds to form cyclic, centrosymmetric R22(8) dimers. By contrast with (I), there are no short Br⋯Br contacts in the structure of (IV).
In the simple amine 2-amino-6-methylbenzo[d]thiazole, which crystallizes with Z′ = 2 in P (GINBIP; Saeed et al., 2007), the molecules are linked into complex chains by a combination of three N—H⋯N hydrogen bonds and one N—H⋯π(arene) hydrogen bond, while in the closely related 2-amino-6-nitrobenzo[d]thiazole (TIJLUT; Glidewell et al., 2001), inversion-related molecules are once again linked by pairwise N—H⋯N hydrogen bonds to form R22(8) dimers, which are further linked by a three-centre N—H⋯(O,O) system to form a three-dimensional network.
5. Synthesis and crystallization
All reagents were obtained commercially and all were used as received. For the synthesis of compound (I), a solution of triethylamine (1.11 g, 0.01 mol) in dry toluene (5 ml) was added to a mixture of 6-aminobenzo[d]thiazole (1.50 g, 0.01 mol) and 3-bromobenzoyl chloride (2.18 g, 0.01 mol) in dry toluene (20 ml), and the resulting mixture was heated under reflux for 4 h. When the reaction was complete, as indicated by TLC monitoring, the mixture was cooled to room temperature and the triethylammonium chloride was removed by filtration. The solvent was then removed under reduced pressure and the resulting solid product was washed with water and then crystallized from ethanol solution. Yield 86%, m.p. 439–441 K: IR (cm−1) 3125 (N—H), 1667 (C=O), 1616 (C=N); NMR (CDCl3) δ(1H) 7.90 (s, 1H, thiazole), 8.21 (s, 1H), NH), 6.8–7.9 (m, 7H, aromatic); MS (70 eV) m/z 335/333, relative intensities 1:1 (M+ + 1). Compound (II) was prepared in a similar manner, using 2-amino-6-methoxybenzo[d]thiazole (1.80 g, 0.01 mol) and 2-nitrobenzoyl chloride (1.85 g, 0.01 mol). Yield 87%, m.p. 468–470 K; IR (cm−1) 3150 (N—H), 1681 (C=O), 1615 (C=N), 1560 and 1346 (nitro); NMR (CDCl3) δ(1H) 3.80 (s, 3H, OMe), 7.2–8.6 (m, 7H, aromatic), 8.10 (s, 1H, NH); MS (70 eV) m/z 330 (M+ + 1). Compound (III) was similarly prepared using 2-amino-6-methoxybenzo[d]thiazole (1.80 g, 0.01 mol) and 5-cyclopropylisoxazole-3-carboxylchloride (1.71 g, 0.01mol). Yield 88%, m.p. 453 K: IR (cm−1) 3120 (N—H), 1676 (C=O), 1625 (C=N); NMR (DMSO-d6) δ(1H) 0.2–2.1 (m, 5H, cyclopropyl), 3.83 (s, 3H, OMe), 6.90 (s, 1H, H-17), 7.20 (d, 1H, J = 7.4 Hz) and 7.46 (d, 1H, J = 7.4 Hz) ((H-14 and H-15), 7.80 (s, 1H, H-4); MS (70 eV) m/z 316 (M+ + 1).
6. Refinement
Crystal data, data collection and structure . One bad outlier reflection (0,23,3) was omitted from the final of compound (II). All H atoms, apart from those in the disordered components of compound (III), were located in difference maps. The H atoms bonded to C atoms were treated as riding atoms in geometrically idealized positions, with C—H distances of 0.93 Å (aromatic and heterocyclic), 0.96 Å (CH3), 0.97 Å (CH2) or 0.98 Å (aliphatic C—H) and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were allowed to rotate but not to tilt, and 1.2 for all other H atoms bonded to C atoms. For the H atoms bonded to N atoms, the atomic coordinates were refined with Uiso(H) = 1.2Ueq(N), giving the N—H distances shown in Table 1. For the disordered methyl group in compound N3, the site occupancies were fixed at 0.5 (see Section 2, above): when these occupancies were refined, the resulting values were 0.504 (7) and 0.496 (7), much as expected. For each of the disordered fragments in (III), the corresponding bonded distances and the 1,3 non-bonded distances were restrained to be equal, subject to s.u. values of 0.01 and 0.02 Å, respectively. In addition, the anisotropic displacement parameters for corresponding pairs of atoms in the 3-cyclopropyl-5-carbonyloxazole fragments were constrained to be equal. Subject to these conditions, the occupancies of this disordered fragment refined to 0.549 (5) and 0.451 (5). The correct orientation of the structure of the crystal of compound (II) chosen for data collection relative to the polar axis direction was established by means of the Flack x parameter (Flack, 1983); x = 0.02 (5), calculated (Parsons et al., 2013) using 708 quotients of the type [(I+) − (I−)]/[(I+) + (I−)].
details are summarized in Table 2
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Supporting information
https://doi.org/10.1107/S2056989021003637/hb7974sup1.cif
contains datablocks global, I, II, III. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021003637/hb7974Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989021003637/hb7974IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989021003637/hb7974IIIsup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021003637/hb7974Isup5.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989021003637/hb7974IIsup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989021003637/hb7974IIIsup7.cml
For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).C14H9BrN2OS | F(000) = 664 |
Mr = 333.19 | Dx = 1.686 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.221 (1) Å | Cell parameters from 2805 reflections |
b = 4.9481 (3) Å | θ = 2.5–27.8° |
c = 10.9981 (6) Å | µ = 3.28 mm−1 |
β = 95.371 (5)° | T = 296 K |
V = 1312.31 (12) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.36 × 0.08 mm |
Oxford Diffraction Xcalibur CCD diffractometer | 2805 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.8°, θmin = 2.5° |
Absorption correction: multi-scan (CrysalisRed; Oxford Diffraction, 2009) | h = −31→24 |
Tmin = 0.168, Tmax = 0.769 | k = −4→6 |
4839 measured reflections | l = −10→14 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0826P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2805 reflections | Δρmax = 1.00 e Å−3 |
175 parameters | Δρmin = −0.73 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 | ||
C1 | 0.82689 (14) | 0.5633 (6) | 0.8202 (3) | 0.0285 (7) | |
C2 | 0.86414 (13) | 0.3673 (6) | 0.7894 (3) | 0.0292 (7) | |
H2 | 0.8588 | 0.2773 | 0.7150 | 0.035* | |
C3 | 0.90946 (13) | 0.3081 (7) | 0.8714 (3) | 0.0300 (7) | |
Br3 | 0.96192 (2) | 0.05035 (8) | 0.82512 (3) | 0.04011 (16) | |
C4 | 0.91689 (15) | 0.4331 (7) | 0.9832 (3) | 0.0387 (8) | |
H4 | 0.9468 | 0.3866 | 1.0383 | 0.046* | |
C5 | 0.88018 (16) | 0.6257 (8) | 1.0131 (3) | 0.0422 (9) | |
H5 | 0.8855 | 0.7119 | 1.0884 | 0.051* | |
C6 | 0.83486 (14) | 0.6942 (7) | 0.9320 (3) | 0.0375 (8) | |
H6 | 0.8101 | 0.8266 | 0.9525 | 0.045* | |
C11 | 0.77814 (13) | 0.6452 (7) | 0.7322 (3) | 0.0307 (7) | |
O11 | 0.76470 (12) | 0.8823 (5) | 0.7208 (3) | 0.0490 (7) | |
N11 | 0.75247 (12) | 0.4425 (6) | 0.6688 (3) | 0.0327 (6) | |
H11 | 0.7634 (15) | 0.274 (7) | 0.689 (3) | 0.039* | |
S11 | 0.55928 (5) | 0.8448 (3) | 0.49883 (12) | 0.0659 (4) | |
C12 | 0.53824 (18) | 0.6976 (10) | 0.3595 (4) | 0.0604 (12) | |
H12 | 0.5048 | 0.7447 | 0.3163 | 0.072* | |
N13 | 0.57051 (15) | 0.5206 (8) | 0.3178 (3) | 0.0594 (10) | |
C13A | 0.61798 (16) | 0.4886 (8) | 0.4010 (3) | 0.0421 (9) | |
C14 | 0.66075 (17) | 0.3153 (10) | 0.3870 (3) | 0.0530 (11) | |
H14 | 0.6603 | 0.2073 | 0.3177 | 0.064* | |
C15 | 0.70478 (16) | 0.3012 (8) | 0.4767 (3) | 0.0455 (9) | |
H15 | 0.7336 | 0.1800 | 0.4687 | 0.055* | |
C16 | 0.70600 (14) | 0.4690 (7) | 0.5795 (3) | 0.0310 (7) | |
C17 | 0.66363 (14) | 0.6445 (7) | 0.5954 (3) | 0.0375 (8) | |
H17 | 0.6645 | 0.7552 | 0.6639 | 0.045* | |
C17A | 0.61882 (14) | 0.6514 (8) | 0.5046 (3) | 0.0397 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0266 (16) | 0.0218 (16) | 0.0363 (16) | 0.0008 (13) | −0.0016 (12) | 0.0046 (14) |
C2 | 0.0307 (17) | 0.0245 (16) | 0.0313 (16) | −0.0011 (13) | −0.0026 (12) | 0.0009 (13) |
C3 | 0.0270 (16) | 0.0284 (17) | 0.0338 (16) | 0.0008 (14) | −0.0008 (12) | 0.0076 (14) |
Br3 | 0.0313 (2) | 0.0432 (3) | 0.0450 (2) | 0.01066 (16) | −0.00006 (14) | 0.00559 (16) |
C4 | 0.040 (2) | 0.045 (2) | 0.0296 (16) | −0.0045 (17) | −0.0045 (14) | 0.0042 (16) |
C5 | 0.047 (2) | 0.046 (2) | 0.0321 (18) | 0.0028 (18) | −0.0032 (15) | −0.0062 (16) |
C6 | 0.038 (2) | 0.035 (2) | 0.0389 (18) | 0.0046 (16) | 0.0054 (14) | −0.0022 (16) |
C11 | 0.0263 (17) | 0.0246 (16) | 0.0404 (18) | 0.0033 (14) | −0.0011 (13) | 0.0048 (14) |
O11 | 0.0486 (17) | 0.0207 (12) | 0.0733 (19) | 0.0058 (11) | −0.0175 (13) | 0.0014 (12) |
N11 | 0.0316 (16) | 0.0199 (14) | 0.0444 (16) | 0.0061 (12) | −0.0078 (12) | 0.0036 (13) |
S11 | 0.0404 (6) | 0.0748 (8) | 0.0777 (8) | 0.0279 (6) | −0.0188 (5) | −0.0133 (7) |
C12 | 0.038 (2) | 0.077 (3) | 0.062 (3) | 0.013 (2) | −0.0154 (18) | 0.006 (2) |
N13 | 0.039 (2) | 0.087 (3) | 0.049 (2) | 0.0027 (19) | −0.0172 (16) | 0.0004 (19) |
C13A | 0.036 (2) | 0.054 (2) | 0.0348 (18) | 0.0020 (17) | −0.0072 (15) | 0.0039 (16) |
C14 | 0.045 (2) | 0.069 (3) | 0.043 (2) | 0.008 (2) | −0.0041 (16) | −0.016 (2) |
C15 | 0.036 (2) | 0.047 (2) | 0.052 (2) | 0.0107 (18) | −0.0015 (16) | −0.0086 (19) |
C16 | 0.0284 (17) | 0.0274 (17) | 0.0358 (17) | 0.0020 (14) | −0.0047 (13) | 0.0043 (14) |
C17 | 0.0339 (19) | 0.0341 (18) | 0.0426 (19) | 0.0060 (16) | −0.0063 (14) | −0.0040 (16) |
C17A | 0.0290 (18) | 0.041 (2) | 0.047 (2) | 0.0100 (16) | −0.0061 (14) | 0.0043 (17) |
C1—C6 | 1.387 (4) | N11—H11 | 0.90 (4) |
C1—C2 | 1.388 (5) | S11—C17A | 1.727 (4) |
C1—C11 | 1.510 (4) | S11—C12 | 1.730 (5) |
C2—C3 | 1.385 (4) | C12—N13 | 1.287 (6) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C4 | 1.373 (5) | N13—C13A | 1.410 (5) |
C3—Br3 | 1.903 (3) | C13A—C14 | 1.365 (6) |
C4—C5 | 1.364 (5) | C13A—C17A | 1.394 (5) |
C4—H4 | 0.9300 | C14—C15 | 1.385 (5) |
C5—C6 | 1.390 (5) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—C16 | 1.400 (5) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C11—O11 | 1.221 (4) | C16—C17 | 1.368 (5) |
C11—N11 | 1.341 (4) | C17—C17A | 1.405 (4) |
N11—C16 | 1.429 (4) | C17—H17 | 0.9300 |
C6—C1—C2 | 120.2 (3) | C17A—S11—C12 | 88.6 (2) |
C6—C1—C11 | 118.6 (3) | N13—C12—S11 | 117.6 (3) |
C2—C1—C11 | 121.2 (3) | N13—C12—H12 | 121.2 |
C3—C2—C1 | 118.8 (3) | S11—C12—H12 | 121.2 |
C3—C2—H2 | 120.6 | C12—N13—C13A | 109.3 (4) |
C1—C2—H2 | 120.6 | C14—C13A—C17A | 120.1 (3) |
C4—C3—C2 | 121.2 (3) | C14—C13A—N13 | 125.4 (4) |
C4—C3—Br3 | 120.4 (2) | C17A—C13A—N13 | 114.5 (4) |
C2—C3—Br3 | 118.4 (2) | C13A—C14—C15 | 119.6 (4) |
C5—C4—C3 | 119.8 (3) | C13A—C14—H14 | 120.2 |
C5—C4—H4 | 120.1 | C15—C14—H14 | 120.2 |
C3—C4—H4 | 120.1 | C14—C15—C16 | 120.1 (3) |
C4—C5—C6 | 120.6 (3) | C14—C15—H15 | 120.0 |
C4—C5—H5 | 119.7 | C16—C15—H15 | 120.0 |
C6—C5—H5 | 119.7 | C17—C16—C15 | 121.4 (3) |
C1—C6—C5 | 119.4 (3) | C17—C16—N11 | 121.5 (3) |
C1—C6—H6 | 120.3 | C15—C16—N11 | 117.1 (3) |
C5—C6—H6 | 120.3 | C16—C17—C17A | 117.6 (3) |
O11—C11—N11 | 124.0 (3) | C16—C17—H17 | 121.2 |
O11—C11—C1 | 120.6 (3) | C17A—C17—H17 | 121.2 |
N11—C11—C1 | 115.4 (3) | C13A—C17A—C17 | 121.2 (3) |
C11—N11—C16 | 125.9 (3) | C13A—C17A—S11 | 110.0 (3) |
C11—N11—H11 | 117 (2) | C17—C17A—S11 | 128.8 (3) |
C16—N11—H11 | 117 (2) | ||
C6—C1—C2—C3 | −0.8 (5) | C12—N13—C13A—C17A | −0.3 (6) |
C11—C1—C2—C3 | 177.2 (3) | C17A—C13A—C14—C15 | 0.4 (7) |
C1—C2—C3—C4 | 2.2 (5) | N13—C13A—C14—C15 | −179.2 (4) |
C1—C2—C3—Br3 | −177.3 (2) | C13A—C14—C15—C16 | −1.7 (7) |
C2—C3—C4—C5 | −2.2 (5) | C14—C15—C16—C17 | 1.6 (6) |
Br3—C3—C4—C5 | 177.3 (3) | C14—C15—C16—N11 | 179.6 (4) |
C3—C4—C5—C6 | 0.8 (6) | C11—N11—C16—C17 | −39.9 (5) |
C2—C1—C6—C5 | −0.5 (5) | C11—N11—C16—C15 | 142.2 (4) |
C11—C1—C6—C5 | −178.6 (3) | C15—C16—C17—C17A | −0.3 (6) |
C4—C5—C6—C1 | 0.5 (6) | N11—C16—C17—C17A | −178.1 (3) |
C6—C1—C11—O11 | 39.0 (5) | C14—C13A—C17A—C17 | 1.0 (6) |
C2—C1—C11—O11 | −139.0 (4) | N13—C13A—C17A—C17 | −179.4 (4) |
C6—C1—C11—N11 | −141.9 (3) | C14—C13A—C17A—S11 | −179.1 (3) |
C2—C1—C11—N11 | 40.0 (4) | N13—C13A—C17A—S11 | 0.6 (5) |
O11—C11—N11—C16 | −0.2 (6) | C16—C17—C17A—C13A | −1.0 (6) |
C1—C11—N11—C16 | −179.2 (3) | C16—C17—C17A—S11 | 179.0 (3) |
C17A—S11—C12—N13 | 0.3 (4) | C12—S11—C17A—C13A | −0.5 (3) |
S11—C12—N13—C13A | 0.0 (6) | C12—S11—C17A—C17 | 179.5 (4) |
C12—N13—C13A—C14 | 179.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O11i | 0.90 (4) | 1.97 (3) | 2.840 (4) | 164 (3) |
C12—H12···N13ii | 0.93 | 2.62 | 3.512 (6) | 161 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+1/2. |
C15H11N3O4S | Dx = 1.475 Mg m−3 |
Mr = 329.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 4785 reflections |
a = 20.085 (2) Å | θ = 2.9–28.8° |
b = 20.165 (2) Å | µ = 0.24 mm−1 |
c = 7.3220 (6) Å | T = 296 K |
V = 2965.5 (5) Å3 | Needle, yellow |
Z = 8 | 0.50 × 0.12 × 0.10 mm |
F(000) = 1360 |
Oxford Diffraction Xcalibur CCD diffractometer | 4784 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2969 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 28.0°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRed; Oxford Diffraction, 2009) | h = −22→25 |
Tmin = 0.787, Tmax = 0.976 | k = −25→23 |
8012 measured reflections | l = −3→9 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.019P)2 + 0.5603P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.19 e Å−3 |
4784 reflections | Δρmin = −0.22 e Å−3 |
423 parameters | Absolute structure: Flack x parameter (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.02 (5) |
Primary atom site location: difference Fourier map |
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 | ||
C11 | 0.6647 (2) | 0.4210 (2) | 0.1128 (7) | 0.0416 (11) | |
C12 | 0.7079 (3) | 0.4721 (2) | 0.0750 (7) | 0.0485 (13) | |
C13 | 0.7447 (3) | 0.4762 (3) | −0.0845 (8) | 0.0585 (15) | |
H13 | 0.7729 | 0.5119 | −0.1054 | 0.070* | |
C14 | 0.7386 (3) | 0.4264 (3) | −0.2113 (8) | 0.0633 (15) | |
H14 | 0.7617 | 0.4286 | −0.3212 | 0.076* | |
C15 | 0.6983 (3) | 0.3734 (3) | −0.1744 (7) | 0.0578 (15) | |
H15 | 0.6958 | 0.3387 | −0.2576 | 0.069* | |
C16 | 0.6612 (3) | 0.3706 (2) | −0.0159 (7) | 0.0494 (13) | |
H16 | 0.6334 | 0.3344 | 0.0050 | 0.059* | |
C111 | 0.6168 (3) | 0.4224 (3) | 0.2709 (7) | 0.0491 (13) | |
O111 | 0.5820 (2) | 0.47044 (17) | 0.3001 (5) | 0.0719 (11) | |
N111 | 0.6129 (2) | 0.36582 (19) | 0.3718 (6) | 0.0468 (12) | |
H111 | 0.642 (2) | 0.339 (2) | 0.348 (7) | 0.056* | |
N121 | 0.7207 (2) | 0.5232 (2) | 0.2121 (8) | 0.0714 (15) | |
O121 | 0.7199 (3) | 0.5076 (2) | 0.3713 (7) | 0.1044 (17) | |
O122 | 0.7336 (2) | 0.57908 (19) | 0.1580 (7) | 0.1033 (16) | |
S111 | 0.52655 (6) | 0.42259 (6) | 0.61418 (19) | 0.0495 (3) | |
C112 | 0.5731 (2) | 0.3570 (2) | 0.5239 (6) | 0.0394 (12) | |
N113 | 0.57191 (18) | 0.30181 (16) | 0.6124 (6) | 0.0433 (9) | |
C13A | 0.5335 (2) | 0.3086 (2) | 0.7691 (7) | 0.0410 (12) | |
C114 | 0.5238 (2) | 0.2610 (2) | 0.9031 (7) | 0.0498 (13) | |
H114 | 0.5421 | 0.2189 | 0.8892 | 0.060* | |
C115 | 0.4873 (2) | 0.2755 (3) | 1.0550 (7) | 0.0549 (15) | |
H115 | 0.4815 | 0.2434 | 1.1447 | 0.066* | |
C116 | 0.4585 (2) | 0.3382 (2) | 1.0778 (7) | 0.0512 (13) | |
C117 | 0.4667 (2) | 0.3862 (2) | 0.9472 (7) | 0.0459 (13) | |
H117 | 0.4474 | 0.4278 | 0.9603 | 0.055* | |
C17A | 0.5048 (2) | 0.3705 (2) | 0.7939 (6) | 0.0421 (12) | |
O116 | 0.42262 (18) | 0.34579 (18) | 1.2344 (5) | 0.0687 (11) | |
C118 | 0.3883 (3) | 0.4068 (3) | 1.2602 (7) | 0.0763 (18) | |
H18A | 0.3605 | 0.4037 | 1.3665 | 0.115* | |
H18B | 0.3613 | 0.4159 | 1.1551 | 0.115* | |
H18C | 0.4200 | 0.4419 | 1.2765 | 0.115* | |
C21 | 0.5587 (2) | 0.10314 (18) | 0.6179 (7) | 0.0356 (10) | |
C22 | 0.4907 (2) | 0.09346 (19) | 0.6067 (7) | 0.0391 (11) | |
C23 | 0.4527 (3) | 0.0724 (2) | 0.7525 (7) | 0.0475 (13) | |
H23 | 0.4071 | 0.0658 | 0.7400 | 0.057* | |
C24 | 0.4839 (3) | 0.0612 (2) | 0.9165 (7) | 0.0506 (14) | |
H24 | 0.4592 | 0.0472 | 1.0168 | 0.061* | |
C25 | 0.5511 (3) | 0.0706 (2) | 0.9332 (7) | 0.0524 (14) | |
H25 | 0.5717 | 0.0631 | 1.0451 | 0.063* | |
C26 | 0.5889 (3) | 0.0912 (2) | 0.7851 (6) | 0.0449 (13) | |
H26 | 0.6346 | 0.0971 | 0.7979 | 0.054* | |
C211 | 0.6042 (2) | 0.1170 (2) | 0.4589 (6) | 0.0404 (12) | |
O211 | 0.61896 (16) | 0.07405 (15) | 0.3509 (4) | 0.0478 (9) | |
N211 | 0.6313 (2) | 0.17844 (19) | 0.4542 (5) | 0.0428 (10) | |
H211 | 0.617 (2) | 0.210 (2) | 0.522 (5) | 0.051* | |
N221 | 0.4558 (2) | 0.1058 (2) | 0.4325 (6) | 0.0519 (11) | |
O221 | 0.48494 (19) | 0.13925 (18) | 0.3175 (5) | 0.0705 (12) | |
O222 | 0.4004 (2) | 0.0816 (2) | 0.4107 (6) | 0.0818 (13) | |
S211 | 0.70172 (6) | 0.15015 (5) | 0.14183 (17) | 0.0474 (3) | |
C212 | 0.6797 (2) | 0.1980 (2) | 0.3302 (6) | 0.0372 (12) | |
N213 | 0.71002 (18) | 0.25434 (17) | 0.3486 (5) | 0.0384 (9) | |
C23A | 0.7553 (2) | 0.2629 (2) | 0.2067 (6) | 0.0375 (12) | |
C214 | 0.7983 (2) | 0.3165 (2) | 0.1862 (6) | 0.0449 (13) | |
H214 | 0.8000 | 0.3498 | 0.2739 | 0.054* | |
C215 | 0.8381 (2) | 0.3192 (2) | 0.0346 (7) | 0.0488 (14) | |
H215 | 0.8683 | 0.3539 | 0.0229 | 0.059* | |
C216 | 0.8344 (2) | 0.2713 (2) | −0.1031 (7) | 0.0468 (13) | |
C217 | 0.7948 (2) | 0.2163 (2) | −0.0808 (6) | 0.0463 (13) | |
H217 | 0.7942 | 0.1825 | −0.1671 | 0.056* | |
C27A | 0.7560 (2) | 0.2131 (2) | 0.0749 (6) | 0.0393 (12) | |
O216 | 0.87332 (17) | 0.28389 (17) | −0.2525 (5) | 0.0614 (10) | |
C218 | 0.8728 (3) | 0.2358 (3) | −0.3963 (7) | 0.0652 (15) | |
H28A | 0.9029 | 0.2494 | −0.4911 | 0.098* | |
H28B | 0.8286 | 0.2321 | −0.4453 | 0.098* | |
H28C | 0.8866 | 0.1935 | −0.3489 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.047 (3) | 0.038 (2) | 0.040 (3) | 0.000 (2) | −0.002 (3) | 0.007 (3) |
C12 | 0.058 (3) | 0.039 (3) | 0.049 (3) | 0.000 (3) | −0.004 (3) | 0.003 (2) |
C13 | 0.055 (4) | 0.055 (4) | 0.066 (4) | −0.004 (3) | 0.005 (3) | 0.013 (3) |
C14 | 0.061 (4) | 0.082 (4) | 0.048 (3) | 0.001 (4) | 0.002 (3) | 0.010 (3) |
C15 | 0.058 (4) | 0.069 (4) | 0.047 (3) | 0.002 (3) | −0.008 (3) | −0.009 (3) |
C16 | 0.046 (3) | 0.050 (3) | 0.053 (3) | 0.001 (3) | −0.011 (3) | −0.002 (3) |
C111 | 0.054 (4) | 0.044 (3) | 0.049 (3) | −0.003 (3) | 0.001 (3) | 0.002 (3) |
O111 | 0.097 (3) | 0.048 (2) | 0.071 (3) | 0.026 (2) | 0.021 (2) | 0.0119 (19) |
N111 | 0.052 (3) | 0.035 (3) | 0.054 (3) | 0.006 (2) | 0.007 (2) | 0.000 (2) |
N121 | 0.083 (4) | 0.050 (3) | 0.081 (4) | −0.005 (3) | 0.001 (3) | −0.006 (3) |
O121 | 0.159 (5) | 0.088 (4) | 0.066 (3) | −0.017 (3) | −0.020 (3) | −0.016 (3) |
O122 | 0.136 (4) | 0.047 (2) | 0.127 (4) | −0.024 (3) | 0.019 (3) | −0.014 (3) |
S111 | 0.0575 (8) | 0.0389 (6) | 0.0519 (8) | 0.0095 (6) | 0.0048 (8) | 0.0053 (7) |
C112 | 0.036 (3) | 0.037 (3) | 0.045 (3) | −0.001 (2) | 0.001 (2) | −0.004 (2) |
N113 | 0.048 (2) | 0.030 (2) | 0.052 (2) | −0.0026 (18) | 0.003 (2) | 0.004 (2) |
C13A | 0.039 (3) | 0.034 (3) | 0.050 (3) | −0.004 (2) | 0.000 (3) | 0.000 (2) |
C114 | 0.055 (4) | 0.032 (3) | 0.062 (4) | 0.001 (3) | 0.003 (3) | 0.003 (3) |
C115 | 0.059 (4) | 0.045 (3) | 0.060 (4) | −0.007 (3) | 0.008 (3) | 0.013 (2) |
C116 | 0.053 (3) | 0.043 (3) | 0.057 (4) | −0.003 (3) | −0.001 (3) | −0.003 (3) |
C117 | 0.051 (3) | 0.036 (3) | 0.051 (3) | 0.002 (3) | 0.003 (3) | 0.003 (2) |
C17A | 0.043 (3) | 0.033 (3) | 0.050 (3) | −0.003 (2) | −0.005 (3) | 0.003 (2) |
O116 | 0.087 (3) | 0.060 (3) | 0.060 (2) | 0.007 (2) | 0.028 (2) | 0.008 (2) |
C118 | 0.087 (5) | 0.071 (4) | 0.071 (4) | 0.014 (4) | 0.027 (4) | −0.002 (3) |
C21 | 0.037 (3) | 0.030 (2) | 0.040 (3) | −0.007 (2) | 0.002 (3) | −0.002 (2) |
C22 | 0.048 (3) | 0.034 (3) | 0.035 (3) | 0.006 (2) | 0.002 (3) | 0.005 (2) |
C23 | 0.041 (3) | 0.045 (3) | 0.056 (4) | 0.004 (3) | 0.006 (3) | −0.001 (3) |
C24 | 0.062 (4) | 0.045 (3) | 0.045 (3) | 0.000 (3) | 0.013 (3) | 0.006 (2) |
C25 | 0.071 (4) | 0.046 (3) | 0.040 (3) | −0.004 (3) | −0.009 (3) | 0.001 (3) |
C26 | 0.043 (3) | 0.050 (3) | 0.042 (3) | −0.005 (3) | −0.008 (3) | −0.003 (3) |
C211 | 0.043 (3) | 0.038 (3) | 0.040 (3) | −0.002 (3) | −0.006 (3) | 0.002 (2) |
O211 | 0.060 (2) | 0.0379 (18) | 0.045 (2) | −0.0039 (17) | 0.0096 (18) | −0.0089 (15) |
N211 | 0.051 (3) | 0.035 (2) | 0.043 (3) | −0.004 (2) | 0.009 (2) | −0.0040 (19) |
N221 | 0.052 (3) | 0.047 (3) | 0.057 (3) | 0.010 (2) | −0.012 (3) | 0.001 (2) |
O221 | 0.077 (3) | 0.080 (3) | 0.054 (2) | 0.005 (2) | −0.007 (2) | 0.027 (2) |
O222 | 0.058 (3) | 0.092 (3) | 0.096 (3) | −0.005 (3) | −0.035 (2) | 0.017 (2) |
S211 | 0.0530 (8) | 0.0404 (7) | 0.0487 (8) | −0.0104 (6) | 0.0091 (7) | −0.0073 (7) |
C212 | 0.041 (3) | 0.032 (3) | 0.039 (3) | −0.002 (2) | 0.002 (2) | 0.002 (2) |
N213 | 0.037 (2) | 0.034 (2) | 0.044 (2) | −0.0061 (19) | 0.008 (2) | −0.0021 (18) |
C23A | 0.035 (3) | 0.032 (3) | 0.045 (3) | −0.002 (2) | −0.006 (2) | −0.003 (2) |
C214 | 0.041 (3) | 0.045 (3) | 0.049 (3) | −0.003 (3) | 0.004 (3) | −0.005 (2) |
C215 | 0.043 (3) | 0.048 (3) | 0.055 (4) | −0.014 (3) | −0.004 (3) | 0.005 (3) |
C216 | 0.039 (3) | 0.056 (3) | 0.046 (3) | −0.003 (3) | 0.007 (3) | 0.007 (3) |
C217 | 0.051 (3) | 0.043 (3) | 0.045 (3) | −0.003 (3) | 0.003 (3) | −0.005 (2) |
C27A | 0.034 (3) | 0.037 (3) | 0.047 (3) | −0.006 (2) | 0.004 (2) | 0.002 (2) |
O216 | 0.063 (3) | 0.068 (3) | 0.053 (2) | −0.017 (2) | 0.012 (2) | 0.0009 (19) |
C218 | 0.058 (4) | 0.088 (4) | 0.050 (3) | −0.010 (3) | 0.011 (3) | 0.002 (3) |
C11—C12 | 1.374 (6) | C21—C22 | 1.382 (5) |
C11—C16 | 1.389 (6) | C21—C26 | 1.388 (6) |
C11—C111 | 1.507 (7) | C21—C211 | 1.507 (6) |
C12—C13 | 1.384 (6) | C22—C23 | 1.379 (6) |
C12—N121 | 1.461 (6) | C22—N221 | 1.477 (6) |
C13—C14 | 1.373 (7) | C23—C24 | 1.373 (6) |
C13—H13 | 0.9300 | C23—H23 | 0.9300 |
C14—C15 | 1.367 (7) | C24—C25 | 1.370 (6) |
C14—H14 | 0.9300 | C24—H24 | 0.9300 |
C15—C16 | 1.381 (7) | C25—C26 | 1.387 (6) |
C15—H15 | 0.9300 | C25—H25 | 0.9300 |
C16—H16 | 0.9300 | C26—H26 | 0.9300 |
C111—O111 | 1.214 (5) | C211—O211 | 1.209 (5) |
C111—N111 | 1.361 (6) | C211—N211 | 1.354 (5) |
N111—C112 | 1.383 (6) | N211—C212 | 1.388 (6) |
N111—H111 | 0.81 (4) | N211—H211 | 0.86 (4) |
N121—O121 | 1.207 (6) | N221—O222 | 1.225 (5) |
N121—O122 | 1.223 (5) | N221—O221 | 1.228 (5) |
S111—C17A | 1.739 (5) | S211—C212 | 1.740 (4) |
S111—C112 | 1.749 (5) | S211—C27A | 1.744 (4) |
C112—N113 | 1.288 (5) | C212—N213 | 1.296 (5) |
N113—C13A | 1.389 (6) | N213—C23A | 1.391 (5) |
C13A—C17A | 1.387 (5) | C23A—C27A | 1.392 (6) |
C13A—C114 | 1.387 (6) | C23A—C214 | 1.393 (6) |
C114—C115 | 1.364 (6) | C214—C215 | 1.368 (6) |
C114—H114 | 0.9300 | C214—H214 | 0.9300 |
C115—C116 | 1.400 (6) | C215—C216 | 1.399 (6) |
C115—H115 | 0.9300 | C215—H215 | 0.9300 |
C116—O116 | 1.364 (6) | C216—O216 | 1.368 (5) |
C116—C117 | 1.370 (6) | C216—C217 | 1.374 (6) |
C117—C17A | 1.395 (6) | C217—C27A | 1.383 (6) |
C117—H117 | 0.9300 | C217—H217 | 0.9300 |
O116—C118 | 1.422 (5) | O216—C218 | 1.432 (6) |
C118—H18A | 0.9600 | C218—H28A | 0.9600 |
C118—H18B | 0.9600 | C218—H28B | 0.9600 |
C118—H18C | 0.9600 | C218—H28C | 0.9600 |
C12—C11—C16 | 116.4 (5) | C22—C21—C26 | 117.4 (4) |
C12—C11—C111 | 123.0 (5) | C22—C21—C211 | 125.5 (4) |
C16—C11—C111 | 120.1 (4) | C26—C21—C211 | 116.6 (4) |
C11—C12—C13 | 123.4 (5) | C23—C22—C21 | 123.0 (5) |
C11—C12—N121 | 120.1 (5) | C23—C22—N221 | 117.3 (4) |
C13—C12—N121 | 116.3 (5) | C21—C22—N221 | 119.7 (4) |
C14—C13—C12 | 118.7 (5) | C24—C23—C22 | 118.4 (5) |
C14—C13—H13 | 120.7 | C24—C23—H23 | 120.8 |
C12—C13—H13 | 120.7 | C22—C23—H23 | 120.8 |
C15—C14—C13 | 119.3 (5) | C25—C24—C23 | 120.3 (5) |
C15—C14—H14 | 120.3 | C25—C24—H24 | 119.8 |
C13—C14—H14 | 120.3 | C23—C24—H24 | 119.8 |
C14—C15—C16 | 121.3 (5) | C24—C25—C26 | 120.8 (5) |
C14—C15—H15 | 119.4 | C24—C25—H25 | 119.6 |
C16—C15—H15 | 119.4 | C26—C25—H25 | 119.6 |
C15—C16—C11 | 120.8 (5) | C25—C26—C21 | 120.1 (5) |
C15—C16—H16 | 119.6 | C25—C26—H26 | 119.9 |
C11—C16—H16 | 119.6 | C21—C26—H26 | 119.9 |
O111—C111—N111 | 122.7 (5) | O211—C211—N211 | 122.7 (5) |
O111—C111—C11 | 121.2 (5) | O211—C211—C21 | 121.4 (4) |
N111—C111—C11 | 116.0 (5) | N211—C211—C21 | 115.6 (4) |
C111—N111—C112 | 125.3 (4) | C211—N211—C212 | 123.9 (4) |
C111—N111—H111 | 113 (4) | C211—N211—H211 | 122 (3) |
C112—N111—H111 | 121 (4) | C212—N211—H211 | 114 (3) |
O121—N121—O122 | 123.8 (5) | O222—N221—O221 | 124.2 (5) |
O121—N121—C12 | 118.5 (5) | O222—N221—C22 | 118.5 (5) |
O122—N121—C12 | 117.7 (5) | O221—N221—C22 | 117.3 (4) |
C17A—S111—C112 | 87.9 (2) | C212—S211—C27A | 88.7 (2) |
N113—C112—N111 | 121.8 (4) | N213—C212—N211 | 120.7 (4) |
N113—C112—S111 | 117.0 (4) | N213—C212—S211 | 116.7 (3) |
N111—C112—S111 | 121.1 (4) | N211—C212—S211 | 122.6 (3) |
C112—N113—C13A | 109.9 (4) | C212—N213—C23A | 109.7 (4) |
C17A—C13A—C114 | 118.2 (4) | N213—C23A—C27A | 115.8 (4) |
C17A—C13A—N113 | 115.3 (4) | N213—C23A—C214 | 125.6 (4) |
C114—C13A—N113 | 126.4 (4) | C27A—C23A—C214 | 118.6 (4) |
C115—C114—C13A | 120.2 (5) | C215—C214—C23A | 118.8 (4) |
C115—C114—H114 | 119.9 | C215—C214—H214 | 120.6 |
C13A—C114—H114 | 119.9 | C23A—C214—H214 | 120.6 |
C114—C115—C116 | 120.9 (5) | C214—C215—C216 | 121.8 (5) |
C114—C115—H115 | 119.6 | C214—C215—H215 | 119.1 |
C116—C115—H115 | 119.6 | C216—C215—H215 | 119.1 |
O116—C116—C117 | 124.8 (5) | O216—C216—C217 | 125.1 (4) |
O116—C116—C115 | 114.8 (5) | O216—C216—C215 | 114.7 (4) |
C117—C116—C115 | 120.3 (5) | C217—C216—C215 | 120.1 (4) |
C116—C117—C17A | 117.9 (4) | C216—C217—C27A | 117.5 (4) |
C116—C117—H117 | 121.1 | C216—C217—H217 | 121.2 |
C17A—C117—H117 | 121.1 | C27A—C217—H217 | 121.2 |
C13A—C17A—C117 | 122.5 (4) | C217—C27A—C23A | 122.9 (4) |
C13A—C17A—S111 | 109.9 (4) | C217—C27A—S211 | 128.2 (4) |
C117—C17A—S111 | 127.6 (4) | C23A—C27A—S211 | 108.9 (3) |
C116—O116—C118 | 117.7 (4) | C216—O216—C218 | 117.3 (4) |
O116—C118—H18A | 109.5 | O216—C218—H28A | 109.5 |
O116—C118—H18B | 109.5 | O216—C218—H28B | 109.5 |
H18A—C118—H18B | 109.5 | H28A—C218—H28B | 109.5 |
O116—C118—H18C | 109.5 | O216—C218—H28C | 109.5 |
H18A—C118—H18C | 109.5 | H28A—C218—H28C | 109.5 |
H18B—C118—H18C | 109.5 | H28B—C218—H28C | 109.5 |
C16—C11—C12—C13 | 2.6 (7) | C26—C21—C22—C23 | −0.5 (6) |
C111—C11—C12—C13 | −169.6 (5) | C211—C21—C22—C23 | 171.1 (4) |
C16—C11—C12—N121 | −172.8 (4) | C26—C21—C22—N221 | 179.6 (4) |
C111—C11—C12—N121 | 15.0 (7) | C211—C21—C22—N221 | −8.8 (6) |
C11—C12—C13—C14 | −0.9 (8) | C21—C22—C23—C24 | 0.7 (7) |
N121—C12—C13—C14 | 174.7 (5) | N221—C22—C23—C24 | −179.3 (4) |
C12—C13—C14—C15 | −2.0 (8) | C22—C23—C24—C25 | −0.3 (7) |
C13—C14—C15—C16 | 3.1 (8) | C23—C24—C25—C26 | −0.3 (7) |
C14—C15—C16—C11 | −1.3 (8) | C24—C25—C26—C21 | 0.6 (7) |
C12—C11—C16—C15 | −1.5 (7) | C22—C21—C26—C25 | −0.2 (6) |
C111—C11—C16—C15 | 170.9 (4) | C211—C21—C26—C25 | −172.6 (4) |
C12—C11—C111—O111 | 47.8 (7) | C22—C21—C211—O211 | −73.2 (6) |
C16—C11—C111—O111 | −124.1 (5) | C26—C21—C211—O211 | 98.5 (5) |
C12—C11—C111—N111 | −135.1 (5) | C22—C21—C211—N211 | 111.9 (5) |
C16—C11—C111—N111 | 53.0 (7) | C26—C21—C211—N211 | −76.5 (5) |
O111—C111—N111—C112 | −4.1 (8) | O211—C211—N211—C212 | −2.0 (7) |
C11—C111—N111—C112 | 178.8 (4) | C21—C211—N211—C212 | 172.8 (4) |
C11—C12—N121—O121 | 33.1 (8) | C23—C22—N221—O222 | −18.2 (6) |
C13—C12—N121—O121 | −142.7 (6) | C21—C22—N221—O222 | 161.7 (4) |
C11—C12—N121—O122 | −148.9 (5) | C23—C22—N221—O221 | 162.7 (4) |
C13—C12—N121—O122 | 35.4 (7) | C21—C22—N221—O221 | −17.4 (6) |
C111—N111—C112—N113 | 179.8 (5) | C211—N211—C212—N213 | −170.5 (4) |
C111—N111—C112—S111 | −5.0 (7) | C211—N211—C212—S211 | 10.9 (6) |
C17A—S111—C112—N113 | 1.6 (4) | C27A—S211—C212—N213 | −1.8 (4) |
C17A—S111—C112—N111 | −173.9 (4) | C27A—S211—C212—N211 | 176.9 (4) |
N111—C112—N113—C13A | 173.7 (4) | N211—C212—N213—C23A | −179.2 (4) |
S111—C112—N113—C13A | −1.8 (5) | S211—C212—N213—C23A | −0.4 (5) |
C112—N113—C13A—C17A | 1.1 (6) | C212—N213—C23A—C27A | 3.3 (5) |
C112—N113—C13A—C114 | −176.2 (5) | C212—N213—C23A—C214 | −177.4 (4) |
C17A—C13A—C114—C115 | −0.5 (7) | N213—C23A—C214—C215 | −177.2 (4) |
N113—C13A—C114—C115 | 176.7 (4) | C27A—C23A—C214—C215 | 2.0 (6) |
C13A—C114—C115—C116 | 0.7 (8) | C23A—C214—C215—C216 | 2.8 (7) |
C114—C115—C116—O116 | 179.1 (4) | C214—C215—C216—O216 | 174.8 (4) |
C114—C115—C116—C117 | −0.1 (8) | C214—C215—C216—C217 | −6.3 (7) |
O116—C116—C117—C17A | −179.8 (4) | O216—C216—C217—C27A | −176.7 (4) |
C115—C116—C117—C17A | −0.7 (7) | C215—C216—C217—C27A | 4.5 (7) |
C114—C13A—C17A—C117 | −0.3 (7) | C216—C217—C27A—C23A | 0.4 (7) |
N113—C13A—C17A—C117 | −177.9 (4) | C216—C217—C27A—S211 | −179.4 (4) |
C114—C13A—C17A—S111 | 177.6 (4) | N213—C23A—C27A—C217 | 175.6 (4) |
N113—C13A—C17A—S111 | 0.1 (5) | C214—C23A—C27A—C217 | −3.7 (7) |
C116—C117—C17A—C13A | 0.9 (7) | N213—C23A—C27A—S211 | −4.5 (5) |
C116—C117—C17A—S111 | −176.6 (4) | C214—C23A—C27A—S211 | 176.2 (3) |
C112—S111—C17A—C13A | −0.8 (3) | C212—S211—C27A—C217 | −176.8 (4) |
C112—S111—C17A—C117 | 177.0 (5) | C212—S211—C27A—C23A | 3.4 (4) |
C117—C116—O116—C118 | 3.3 (7) | C217—C216—O216—C218 | −0.3 (7) |
C115—C116—O116—C118 | −175.8 (4) | C215—C216—O216—C218 | 178.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N111—H111···N213 | 0.82 (4) | 2.19 (4) | 2.981 (5) | 165 (4) |
N211—H211···N113 | 0.86 (4) | 2.17 (4) | 2.992 (5) | 162 (4) |
C13—H13···O211i | 0.93 | 2.53 | 3.408 (7) | 158 |
C25—H25···O211ii | 0.93 | 2.44 | 3.349 (6) | 165 |
C115—H115···O221ii | 0.93 | 2.45 | 3.353 (7) | 163 |
C117—H117···O111iii | 0.93 | 2.44 | 3.236 (5) | 144 |
C217—H217···O122iv | 0.93 | 2.51 | 3.412 (6) | 164 |
C16—H16···Cg1v | 0.93 | 2.84 | 3.484 (6) | 128 |
Symmetry codes: (i) −x+3/2, y+1/2, z−1/2; (ii) x, y, z+1; (iii) −x+1, −y+1, z+1/2; (iv) −x+3/2, y−1/2, z−1/2; (v) x, y, z−1. |
C15H13N3O3S | F(000) = 1312 |
Mr = 315.34 | Dx = 1.455 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.720 (1) Å | Cell parameters from 3118 reflections |
b = 11.5255 (8) Å | θ = 2.9–27.8° |
c = 14.7905 (9) Å | µ = 0.24 mm−1 |
β = 115.52 (1)° | T = 296 K |
V = 2879.8 (4) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.20 × 0.10 mm |
Oxford Diffraction Xcalibur CCD diffractometer | 3118 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1730 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 27.8°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRed; Oxford Diffraction, 2009) | h = −24→19 |
Tmin = 0.908, Tmax = 0.976 | k = −15→9 |
5937 measured reflections | l = −18→19 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0504P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3118 reflections | Δρmax = 0.23 e Å−3 |
268 parameters | Δρmin = −0.24 e Å−3 |
26 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 | Occ. (<1) | |
C31B | 0.45159 (15) | 0.6697 (2) | 0.4342 (2) | 0.0494 (7) | 0.451 (5) |
O31B | 0.4916 (12) | 0.682 (3) | 0.5246 (5) | 0.056 (3) | 0.451 (5) |
O1B | 0.2557 (4) | 0.7800 (10) | 0.2806 (7) | 0.0511 (13) | 0.451 (5) |
N2B | 0.3373 (6) | 0.766 (3) | 0.3053 (16) | 0.0495 (13) | 0.451 (5) |
C3B | 0.3650 (8) | 0.703 (4) | 0.387 (3) | 0.0441 (12) | 0.451 (5) |
C4B | 0.3059 (8) | 0.673 (4) | 0.417 (2) | 0.0492 (13) | 0.451 (5) |
H4B | 0.3114 | 0.6272 | 0.4713 | 0.059* | 0.451 (5) |
C5B | 0.2392 (4) | 0.7242 (13) | 0.3499 (8) | 0.0446 (17) | 0.451 (5) |
C51 | 0.1558 (4) | 0.7226 (8) | 0.3338 (5) | 0.057 (2) | 0.451 (5) |
H51 | 0.1464 | 0.6824 | 0.3860 | 0.068* | 0.451 (5) |
C52 | 0.0910 (5) | 0.7088 (8) | 0.2300 (6) | 0.055 (3) | 0.451 (5) |
H52A | 0.1058 | 0.7077 | 0.1747 | 0.066* | 0.451 (5) |
H52B | 0.0467 | 0.6593 | 0.2214 | 0.066* | 0.451 (5) |
C53 | 0.0996 (4) | 0.8175 (6) | 0.2835 (5) | 0.067 (2) | 0.451 (5) |
H53A | 0.0602 | 0.8357 | 0.3077 | 0.080* | 0.451 (5) |
H53B | 0.1194 | 0.8841 | 0.2611 | 0.080* | 0.451 (5) |
C31A | 0.45159 (15) | 0.6697 (2) | 0.4342 (2) | 0.0494 (7) | 0.549 (5) |
O31A | 0.4786 (9) | 0.655 (2) | 0.5251 (4) | 0.056 (3) | 0.549 (5) |
O1A | 0.2719 (3) | 0.8029 (8) | 0.2617 (5) | 0.0511 (13) | 0.549 (5) |
N2A | 0.3533 (5) | 0.778 (2) | 0.2975 (13) | 0.0495 (13) | 0.549 (5) |
C3A | 0.3683 (6) | 0.710 (4) | 0.374 (2) | 0.0441 (12) | 0.549 (5) |
C4A | 0.3025 (6) | 0.690 (3) | 0.3936 (17) | 0.0492 (13) | 0.549 (5) |
H4A | 0.3002 | 0.6471 | 0.4455 | 0.059* | 0.549 (5) |
C5A | 0.2435 (3) | 0.7473 (10) | 0.3203 (7) | 0.0446 (17) | 0.549 (5) |
C61 | 0.1581 (3) | 0.7625 (6) | 0.2904 (5) | 0.058 (2) | 0.549 (5) |
H61 | 0.1352 | 0.8351 | 0.2554 | 0.069* | 0.549 (5) |
C62 | 0.1039 (5) | 0.6592 (7) | 0.2597 (6) | 0.067 (3) | 0.549 (5) |
H62A | 0.0511 | 0.6696 | 0.2064 | 0.080* | 0.549 (5) |
H62B | 0.1272 | 0.5836 | 0.2613 | 0.080* | 0.549 (5) |
C63 | 0.1224 (3) | 0.7162 (6) | 0.3547 (4) | 0.068 (2) | 0.549 (5) |
H63A | 0.1569 | 0.6757 | 0.4153 | 0.082* | 0.549 (5) |
H63B | 0.0809 | 0.7616 | 0.3605 | 0.082* | 0.549 (5) |
N31 | 0.48732 (12) | 0.6444 (2) | 0.37429 (16) | 0.0474 (6) | |
H31 | 0.4615 (16) | 0.637 (2) | 0.314 (2) | 0.057* | |
S11 | 0.63319 (4) | 0.63305 (6) | 0.53535 (5) | 0.0480 (2) | |
C12 | 0.56815 (13) | 0.6228 (2) | 0.40899 (18) | 0.0404 (6) | |
N13 | 0.59782 (12) | 0.59878 (19) | 0.34675 (15) | 0.0460 (6) | |
C13A | 0.68009 (15) | 0.5844 (2) | 0.39970 (19) | 0.0436 (6) | |
C14 | 0.73158 (16) | 0.5543 (2) | 0.3582 (2) | 0.0556 (8) | |
H14 | 0.7124 | 0.5405 | 0.2898 | 0.067* | |
C15 | 0.81099 (17) | 0.5452 (3) | 0.4194 (2) | 0.0581 (8) | |
H15 | 0.8454 | 0.5232 | 0.3921 | 0.070* | |
C17 | 0.79097 (14) | 0.5970 (2) | 0.5647 (2) | 0.0490 (7) | |
H17 | 0.8106 | 0.6113 | 0.6330 | 0.059* | |
C17A | 0.71007 (14) | 0.6035 (2) | 0.50220 (19) | 0.0406 (6) | |
C16A | 0.84091 (15) | 0.5684 (2) | 0.5213 (2) | 0.0528 (7) | 0.5 |
O16 | 0.9220 (6) | 0.552 (5) | 0.577 (3) | 0.065 (7) | 0.5 |
C18 | 0.9590 (3) | 0.5892 (5) | 0.6867 (4) | 0.0638 (16) | 0.5 |
H18A | 1.0156 | 0.5873 | 0.7124 | 0.096* | 0.5 |
H18B | 0.9424 | 0.5369 | 0.7246 | 0.096* | 0.5 |
H18C | 0.9422 | 0.6665 | 0.6922 | 0.096* | 0.5 |
C16B | 0.84091 (15) | 0.5684 (2) | 0.5213 (2) | 0.0528 (7) | 0.5 |
O17 | 0.9206 (5) | 0.576 (5) | 0.581 (3) | 0.061 (6) | 0.5 |
C19 | 0.9693 (3) | 0.5307 (6) | 0.5324 (4) | 0.0719 (19) | 0.5 |
H19A | 1.0243 | 0.5366 | 0.5780 | 0.108* | 0.5 |
H19B | 0.9591 | 0.5753 | 0.4733 | 0.108* | 0.5 |
H19C | 0.9561 | 0.4509 | 0.5143 | 0.108* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C31B | 0.0317 (14) | 0.065 (2) | 0.0495 (16) | −0.0006 (13) | 0.0160 (13) | 0.0014 (15) |
O31B | 0.024 (5) | 0.096 (10) | 0.0478 (12) | −0.009 (3) | 0.0161 (11) | 0.0036 (15) |
O1B | 0.030 (3) | 0.072 (4) | 0.055 (3) | 0.008 (2) | 0.0215 (15) | 0.0136 (19) |
N2B | 0.023 (3) | 0.068 (5) | 0.059 (3) | 0.002 (5) | 0.019 (3) | 0.0044 (17) |
C3B | 0.0288 (15) | 0.053 (4) | 0.049 (6) | −0.001 (2) | 0.0146 (14) | 0.002 (3) |
C4B | 0.0340 (18) | 0.053 (8) | 0.062 (9) | 0.0033 (16) | 0.022 (3) | 0.017 (4) |
C5B | 0.0375 (19) | 0.055 (5) | 0.051 (5) | −0.002 (2) | 0.028 (2) | 0.004 (4) |
C51 | 0.039 (4) | 0.084 (7) | 0.058 (5) | 0.002 (5) | 0.032 (4) | 0.011 (5) |
C52 | 0.033 (4) | 0.058 (7) | 0.077 (6) | −0.007 (4) | 0.026 (4) | 0.005 (5) |
C53 | 0.043 (4) | 0.058 (5) | 0.103 (6) | −0.002 (3) | 0.035 (4) | −0.007 (5) |
C31A | 0.0317 (14) | 0.065 (2) | 0.0495 (16) | −0.0006 (13) | 0.0160 (13) | 0.0014 (15) |
O31A | 0.024 (5) | 0.096 (10) | 0.0478 (12) | −0.009 (3) | 0.0161 (11) | 0.0036 (15) |
O1A | 0.030 (3) | 0.072 (4) | 0.055 (3) | 0.008 (2) | 0.0215 (15) | 0.0136 (19) |
N2A | 0.023 (3) | 0.068 (5) | 0.059 (3) | 0.002 (5) | 0.019 (3) | 0.0044 (17) |
C3A | 0.0288 (15) | 0.053 (4) | 0.049 (6) | −0.001 (2) | 0.0146 (14) | 0.002 (3) |
C4A | 0.0340 (18) | 0.053 (8) | 0.062 (9) | 0.0033 (16) | 0.022 (3) | 0.017 (4) |
C5A | 0.0375 (19) | 0.055 (5) | 0.051 (5) | −0.002 (2) | 0.028 (2) | 0.004 (4) |
C61 | 0.028 (3) | 0.074 (5) | 0.074 (5) | 0.007 (3) | 0.024 (3) | 0.013 (4) |
C62 | 0.035 (4) | 0.087 (7) | 0.079 (5) | −0.011 (5) | 0.025 (4) | −0.018 (6) |
C63 | 0.039 (4) | 0.109 (6) | 0.067 (4) | 0.001 (4) | 0.033 (3) | 0.000 (4) |
N31 | 0.0273 (11) | 0.0672 (16) | 0.0421 (12) | 0.0001 (11) | 0.0096 (10) | −0.0008 (13) |
S11 | 0.0288 (3) | 0.0700 (5) | 0.0427 (4) | 0.0041 (3) | 0.0131 (3) | −0.0019 (4) |
C12 | 0.0298 (13) | 0.0478 (17) | 0.0410 (13) | 0.0009 (12) | 0.0127 (11) | −0.0001 (13) |
N13 | 0.0367 (12) | 0.0544 (15) | 0.0441 (12) | 0.0048 (10) | 0.0146 (10) | −0.0003 (11) |
C13A | 0.0395 (15) | 0.0444 (17) | 0.0486 (16) | 0.0060 (13) | 0.0204 (13) | 0.0046 (13) |
C14 | 0.0545 (18) | 0.064 (2) | 0.0533 (17) | 0.0134 (15) | 0.0280 (15) | 0.0053 (15) |
C15 | 0.0493 (18) | 0.067 (2) | 0.071 (2) | 0.0172 (15) | 0.0378 (16) | 0.0107 (17) |
C17 | 0.0335 (14) | 0.0581 (19) | 0.0534 (16) | 0.0036 (13) | 0.0168 (13) | −0.0011 (14) |
C17A | 0.0321 (13) | 0.0413 (16) | 0.0490 (15) | 0.0024 (11) | 0.0180 (12) | 0.0013 (12) |
C16A | 0.0331 (15) | 0.0533 (19) | 0.073 (2) | 0.0085 (13) | 0.0232 (15) | 0.0127 (16) |
O16 | 0.038 (6) | 0.081 (17) | 0.067 (8) | 0.012 (4) | 0.014 (5) | 0.001 (8) |
C18 | 0.039 (3) | 0.064 (4) | 0.070 (4) | −0.001 (3) | 0.006 (3) | 0.011 (3) |
C16B | 0.0331 (15) | 0.0533 (19) | 0.073 (2) | 0.0085 (13) | 0.0232 (15) | 0.0127 (16) |
O17 | 0.031 (5) | 0.084 (18) | 0.069 (7) | 0.013 (4) | 0.022 (5) | −0.008 (7) |
C19 | 0.032 (3) | 0.113 (6) | 0.074 (4) | 0.009 (3) | 0.026 (3) | 0.003 (4) |
C31B—O31B | 1.227 (7) | C62—H62B | 0.9700 |
C31B—N31 | 1.352 (3) | C63—H63A | 0.9700 |
C31B—C3B | 1.512 (6) | C63—H63B | 0.9700 |
O1B—C5B | 1.353 (6) | N31—C12 | 1.395 (3) |
O1B—N2B | 1.419 (6) | N31—H31 | 0.82 (3) |
N2B—C3B | 1.310 (6) | S11—C12 | 1.740 (2) |
C3B—C4B | 1.401 (6) | S11—C17A | 1.742 (2) |
C4B—C5B | 1.350 (7) | C12—N13 | 1.293 (3) |
C4B—H4B | 0.9300 | N13—C13A | 1.405 (3) |
C5B—C51 | 1.474 (7) | C13A—C17A | 1.389 (3) |
C51—C53 | 1.477 (7) | C13A—C14 | 1.391 (3) |
C51—C52 | 1.499 (7) | C14—C15 | 1.371 (4) |
C51—H51 | 0.9800 | C14—H14 | 0.9300 |
C52—C53 | 1.454 (8) | C15—C16A | 1.389 (4) |
C52—H52A | 0.9700 | C15—H15 | 0.9300 |
C52—H52B | 0.9700 | C17—C16A | 1.383 (3) |
C53—H53A | 0.9700 | C17—C17A | 1.395 (3) |
C53—H53B | 0.9700 | C17—H17 | 0.9300 |
O1A—C5A | 1.357 (5) | C16A—O16 | 1.393 (8) |
O1A—N2A | 1.412 (5) | O16—C18 | 1.52 (4) |
N2A—C3A | 1.308 (6) | C18—C18i | 1.840 (10) |
C3A—C4A | 1.399 (5) | C18—H18A | 0.9600 |
C4A—C5A | 1.342 (6) | C18—H18B | 0.9600 |
C4A—H4A | 0.9300 | C18—H18C | 0.9600 |
C5A—C61 | 1.473 (6) | O17—C19 | 1.48 (4) |
C61—C63 | 1.478 (6) | C19—C19ii | 1.920 (11) |
C61—C62 | 1.503 (7) | C19—H19A | 0.9600 |
C61—H61 | 0.9800 | C19—H19B | 0.9600 |
C62—C63 | 1.451 (7) | C19—H19C | 0.9600 |
C62—H62A | 0.9700 | ||
O31B—C31B—N31 | 119.8 (12) | C62—C63—C61 | 61.8 (4) |
O31B—C31B—C3B | 120.3 (12) | C62—C63—H63A | 117.6 |
N31—C31B—C3B | 119.0 (14) | C61—C63—H63A | 117.6 |
C5B—O1B—N2B | 108.9 (5) | C62—C63—H63B | 117.6 |
C3B—N2B—O1B | 104.8 (5) | C61—C63—H63B | 117.6 |
N2B—C3B—C4B | 112.0 (5) | H63A—C63—H63B | 114.7 |
N2B—C3B—C31B | 119.2 (7) | C31B—N31—C12 | 124.2 (2) |
C4B—C3B—C31B | 128.8 (7) | C31B—N31—H31 | 120.8 (19) |
C5B—C4B—C3B | 105.5 (6) | C12—N31—H31 | 114.9 (19) |
C5B—C4B—H4B | 127.3 | C12—S11—C17A | 87.99 (11) |
C3B—C4B—H4B | 127.3 | N13—C12—N31 | 120.4 (2) |
C4B—C5B—O1B | 108.8 (6) | N13—C12—S11 | 117.56 (18) |
C4B—C5B—C51 | 133.9 (7) | N31—C12—S11 | 121.94 (18) |
O1B—C5B—C51 | 117.1 (6) | C12—N13—C13A | 109.4 (2) |
C5B—C51—C53 | 123.2 (8) | C17A—C13A—C14 | 119.4 (2) |
C5B—C51—C52 | 120.0 (7) | C17A—C13A—N13 | 114.9 (2) |
C53—C51—C52 | 58.5 (4) | C14—C13A—N13 | 125.8 (2) |
C5B—C51—H51 | 114.6 | C15—C14—C13A | 119.2 (3) |
C53—C51—H51 | 114.6 | C15—C14—H14 | 120.4 |
C52—C51—H51 | 114.6 | C13A—C14—H14 | 120.4 |
C53—C52—C51 | 60.0 (4) | C14—C15—C16A | 121.1 (3) |
C53—C52—H52A | 117.8 | C14—C15—H15 | 119.4 |
C51—C52—H52A | 117.8 | C16A—C15—H15 | 119.4 |
C53—C52—H52B | 117.8 | C16A—C17—C17A | 117.6 (3) |
C51—C52—H52B | 117.8 | C16A—C17—H17 | 121.2 |
H52A—C52—H52B | 114.9 | C17A—C17—H17 | 121.2 |
C52—C53—C51 | 61.5 (4) | C13A—C17A—C17 | 121.8 (2) |
C52—C53—H53A | 117.6 | C13A—C17A—S11 | 110.11 (18) |
C51—C53—H53A | 117.6 | C17—C17A—S11 | 128.1 (2) |
C52—C53—H53B | 117.6 | C17—C16A—C15 | 120.8 (3) |
C51—C53—H53B | 117.6 | C17—C16A—O16 | 123 (2) |
H53A—C53—H53B | 114.7 | C15—C16A—O16 | 116 (2) |
C5A—O1A—N2A | 108.8 (4) | C16A—O16—C18 | 118 (3) |
C3A—N2A—O1A | 103.9 (4) | O16—C18—C18i | 151.6 (14) |
N2A—C3A—C4A | 113.4 (5) | O16—C18—H18A | 109.5 |
C5A—C4A—C3A | 104.2 (5) | C18i—C18—H18A | 45.7 |
C5A—C4A—H4A | 127.9 | O16—C18—H18B | 109.5 |
C3A—C4A—H4A | 127.9 | C18i—C18—H18B | 75.2 |
C4A—C5A—O1A | 109.6 (5) | H18A—C18—H18B | 109.5 |
C4A—C5A—C61 | 135.3 (6) | O16—C18—H18C | 109.5 |
O1A—C5A—C61 | 115.1 (5) | C18i—C18—H18C | 94.3 |
C5A—C61—C63 | 119.8 (5) | H18A—C18—H18C | 109.5 |
C5A—C61—C62 | 120.0 (7) | H18B—C18—H18C | 109.5 |
C63—C61—C62 | 58.2 (4) | O17—C19—C19ii | 178.6 (18) |
C5A—C61—H61 | 115.6 | O17—C19—H19A | 109.5 |
C63—C61—H61 | 115.6 | C19ii—C19—H19A | 71.7 |
C62—C61—H61 | 115.6 | O17—C19—H19B | 109.5 |
C63—C62—C61 | 60.0 (3) | C19ii—C19—H19B | 70.7 |
C63—C62—H62A | 117.8 | H19A—C19—H19B | 109.5 |
C61—C62—H62A | 117.8 | O17—C19—H19C | 109.5 |
C63—C62—H62B | 117.8 | C19ii—C19—H19C | 69.2 |
C61—C62—H62B | 117.8 | H19A—C19—H19C | 109.5 |
H62A—C62—H62B | 114.9 | H19B—C19—H19C | 109.5 |
C5B—O1B—N2B—C3B | 0 (4) | C5A—C61—C62—C63 | 108.5 (7) |
O1B—N2B—C3B—C4B | 1 (6) | C5A—C61—C63—C62 | −108.9 (8) |
O1B—N2B—C3B—C31B | 179 (4) | O31B—C31B—N31—C12 | 4.6 (15) |
O31B—C31B—C3B—N2B | 132 (4) | C3B—C31B—N31—C12 | 174 (2) |
N31—C31B—C3B—N2B | −37 (6) | C31B—N31—C12—N13 | 179.8 (3) |
O31B—C31B—C3B—C4B | −49 (6) | C31B—N31—C12—S11 | −3.1 (4) |
N31—C31B—C3B—C4B | 141 (5) | C17A—S11—C12—N13 | 0.7 (2) |
N2B—C3B—C4B—C5B | −2 (6) | C17A—S11—C12—N31 | −176.5 (2) |
C31B—C3B—C4B—C5B | 180 (4) | N31—C12—N13—C13A | 178.1 (2) |
C3B—C4B—C5B—O1B | 2 (5) | S11—C12—N13—C13A | 0.9 (3) |
C3B—C4B—C5B—C51 | 176 (3) | C12—N13—C13A—C17A | −2.6 (3) |
N2B—O1B—C5B—C4B | −1 (3) | C12—N13—C13A—C14 | 177.8 (3) |
N2B—O1B—C5B—C51 | −176.4 (18) | C17A—C13A—C14—C15 | −0.6 (4) |
C4B—C5B—C51—C53 | 155 (3) | N13—C13A—C14—C15 | 178.9 (2) |
O1B—C5B—C51—C53 | −31.4 (18) | C13A—C14—C15—C16A | −1.6 (4) |
C4B—C5B—C51—C52 | −135 (3) | C14—C13A—C17A—C17 | 2.0 (4) |
O1B—C5B—C51—C52 | 38.5 (18) | N13—C13A—C17A—C17 | −177.5 (2) |
C5B—C51—C52—C53 | −112.8 (9) | C14—C13A—C17A—S11 | −177.3 (2) |
C5B—C51—C53—C52 | 107.4 (10) | N13—C13A—C17A—S11 | 3.2 (3) |
C5A—O1A—N2A—C3A | 0 (3) | C16A—C17—C17A—C13A | −1.2 (4) |
O1A—N2A—C3A—C4A | −2 (5) | C16A—C17—C17A—S11 | 177.9 (2) |
N2A—C3A—C4A—C5A | 3 (5) | C12—S11—C17A—C13A | −2.1 (2) |
C3A—C4A—C5A—O1A | −2 (4) | C12—S11—C17A—C17 | 178.7 (3) |
C3A—C4A—C5A—C61 | 178 (2) | C17A—C17—C16A—C15 | −1.1 (4) |
N2A—O1A—C5A—C4A | 2 (2) | C17A—C17—C16A—O16 | −176 (3) |
N2A—O1A—C5A—C61 | −178.5 (14) | C14—C15—C16A—C17 | 2.5 (5) |
C4A—C5A—C61—C63 | 6 (3) | C14—C15—C16A—O16 | 178 (3) |
O1A—C5A—C61—C63 | −173.6 (9) | C17—C16A—O16—C18 | −12 (5) |
C4A—C5A—C61—C62 | −62 (3) | C15—C16A—O16—C18 | 173 (3) |
O1A—C5A—C61—C62 | 118.1 (10) | C16A—O16—C18—C18i | 165.7 (9) |
Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N31—H31···N13iii | 0.82 (3) | 2.19 (3) | 3.003 (3) | 173 (2) |
C17—H17···O1Aiv | 0.93 | 2.51 | 3.293 (7) | 142 |
C17—H17···N2Aiv | 0.93 | 2.55 | 3.440 (19) | 160 |
C63—H63B···O31Av | 0.97 | 2.58 | 3.440 (18) | 148 |
Symmetry codes: (iii) −x+1, y, −z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+1/2, −y+3/2, −z+1. |
Cg1 represents the centroid of the ring C13A/C17A/C117/C116/C115/C114 |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
(I) | N11—H11···O11i | 0.90 (4) | 1.97 (3) | 2.840 (4) | 164 (3)) |
C12—H12···N13ii | 0.93 | 2.62 | 3.512 (6) | 161 | |
(II) | N111—H111···N213 | 0.82 (4) | 2.19 (4) | 2.981 (5) | 165 (4) |
N211—H211···N113 | 0.86 (4) | 2.17 (4) | 2.992 (5) | 162 (4) | |
C13—H13···O211iii | 0.93 | 2.53 | 3.408 (7) | 158 | |
C25—H25···O211iv | 0.93 | 2.44 | 3.349 (6) | 165 | |
C115—H115···O221iv | 0.93 | 2.45 | 3.353 (7) | 163 | |
C117—H117···O111v | 0.93 | 2.44 | 3.236 (5) | 144 | |
C217—H217···O122vi | 0.93 | 2.51 | 3.412 (6) | 164 | |
C16—H16···Cg1vii | 0.93 | 2.84 | 3.484 (6) | 128 | |
(III) | N31—H31···N13viii | 0.82 (3) | 2.19 (3) | 3.003 (3) | 173 (2) |
C17—H17···O1Aix | 0.93 | 2.51 | 3.293 (7) | 142 | |
C17—H17···N2AAix | 0.93 | 2.55 | 3.440 (19) | 160 | |
C63—H63B···O31Ax | 0.97 | 2.58 | 3.440 (18) | 148 |
Symmetry codes: (i) x, -1 + y, z; (ii) 1 - x, 1/2 + y, 1/2 - z; (iii) 3/2 - x, 1/2 + y, -1/2 - z; (iv) x, y, 1 + z; (v) 1 - x, 1 - y, 1/2 + z; (vi) 3/2 - x, -1/2 + y, -1/2 - z; (vii) x, y, -1 + z; (viii) 1 - x, y, 1/2 - z; (ix) 1/2 + x, 3/2 - y, 1/2 + z; (x) 1/2 - x, 3/2 - y, 1 - z. |
Acknowledgements
NM thanks the University of Mysore for research facilities.
Funding information
HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.
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