research communications
Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzylidene-N-methyl-2-(thiophen-2-yl)acetohydrazides
aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos–FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, Brazil, bInstituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, Brazil, and cDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: w.harrison@abdn.ac.uk
The syntheses and crystal structures of (E)-N′-(3-cyanobenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N′-(4-methoxybenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two molecules in the with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thiophene rings in (I) are well ordered, whereas those in (II) exhibit `flip' rotational disorder [occupancies 0.662 (2) and 0.338 (2) for molecule 1, and 0.549 (3) and 0.451 (3) for molecule 2]. The packing for (I) features short C—H⋯O interactions arising from the C—H grouping adjacent to the cyanide group and C—H⋯Nc (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H⋯π interactions interlink the chains into a three-dimensional network. The packing for (II) features numerous C—H⋯O and C—H⋯π interactions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).
Keywords: crystal structure; carbohydrazide; methylation; weak hydrogen bonds.
1. Chemical context
Thiophene derivatives are important ). A valuable group of thiophenyl derivatives are the series of acylhydrazine derivatives, 2-[ArCH=N—NRCO(CH2)n-thiophene, where R = Me or H, and n = 0 or 1. Recent studies have investigated their anti-TB activities (Cardoso et al., 2014) and anti-cancer activities (Cardoso et al., 2017). We now report the crystal structures of two derivatives of the 2-[ArCH=N—NMeCOCH2-thiophene series, bearing different substituents at the meta and para positions of the benzene ring, viz. (E)-N′-(3-cyanobenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, (I), and (E)-N′-(4-methoxybenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, (II). These complement our recent structural study (Cardoso et al., 2016a) of isomeric ortho-, meta- and para-nitro derivatives in the same family.
widely used as building blocks in many agrochemicals and pharmaceuticals (Swanston, 20062. Structural commentary
The molecular structure of (I) is shown in Fig. 1, which indicates the presence of two molecules, A (containing S1) and B (containing S2), in the of the triclinic The thiophene rings are well ordered [C11—S1—C14 = 92.14 (8); C26—S2—C29 = 92.39 (8)°]. For molecule A, the dihedral angle between the thiophene and benzene rings is 64.44 (5)°. The central CH=N—N(CH3)—C(=O) fragment (C7/C8/C9/N1/N2/O1) in (I) is almost planar (r.m.s. deviation = 0.022 Å) and subtends dihedral angles of 2.28 (9) and 66.47 (5)° with the benzene and thiophene rings, respectively. The major twist in the molecule occurs about the C9—C10 bond [N2—C9—C10—C11 = −91.98 (16)°], giving the molecule an approximate overall L-shape. As seen for related compounds (Cardoso et al., 2016a), the N1—N2 bond length of 1.3797 (17) Å is significantly shortened compared to the reference value of ∼1.41 Å for an isolated N—N single bond and the C9—N2 amide bond of 1.3702 (19) Å is lengthened: these distance data can be interpreted in terms of significant delocalization of electrons over the methylidene–acetohydrazide fragment of the molecule. For molecule B, comparable geometrical data are as follows: C16–C21 benzene ring = A, C26–C29/S2 thiophene ring = B, C22/N4/N5/C23/C4/O2 linking chain (r.m.s. deviation = 0.033 Å) = C; dihedral angles A/B, A/C and B/C = 66.40 (8), 10.85 (9) and 58.33 (5)°, respectively; N5—C24—C25—C26 = −82.29 (18)°, N4—N5 = 1.3651 (17), C24—N5 = 1.3766 (19) Å. These data are generally similar to the corresponding values for molecule A and the r.m.s. overlay fit of molecules A and B of 0.334 Å and visual inspection (Fig. 2) confirms this.
Compound (II) (Fig. 3) also crystallizes in P with Z′ = 2 (molecule A containing S1 and molecule B containing S2). In this case, both thiophene ring show `flip' disorder over two conformations rotated by ∼180° in a 0.662 (2):0.338 (2) ratio about the C10—C11 bond for A and a 0.549 (3):0.451 (3) ratio about the C25—C26 bond for B. The major orientation for A has the S atom pointing towards the benzene ring. For B, the disorder is close to statistical, but there is a slight preference for the S atom to point away from the benzene ring. For molecule A, the dihedral angle between the thiophene and benzene rings is 79.38 (7)°. The central CH=N—N(CH3)—C(=O) fragment (C7/C8/C9/N1/N2/O1) is almost planar (r.m.s. deviation = 0.013 Å) and the benzene and thiophene rings are twisted from it by 0.89 (12) and 78.80 (9)°, respectively. Thus, as for (I), the major twist in the molecule occurs about C9—C10 [N2—C9—C10—C11 = −86.1 (3)°], and an approximate overall L-shape results. Atom C15 of the methoxy group deviates slightly, by 0.068 (2) Å, from the plane of its attached ring. The N1—N2 [1.3780 (16) Å] and C9—N2 [1.3690 (18) Å] bond lengths show the same pattern as for (I), again indicating delocalization of electrons over the central grouping. Corresponding data for molecule B in (II) are as follows: C16–C21 benzene ring = A, C26–C29/S2 thiophene ring = B, C22/N3/N4/C23/C4/O3 linking chain (r.m.s. deviation = 0.021 Å) = C; dihedral angles A/B, A/C and B/C = 70.61 (8), 9.73 (17) and 77.66 (6)°, respectively; N4—C24—C25—C26 = 84.33 (17)°, N3—N4 = 1.3768 (17), C24—N4 = 1.375 (2) Å, displacement of C30 from the A ring = 0.155 (3) Å. Again, the two molecules have broadly similar conformations (Fig. 4) and the r.m.s. overlay fit is 0.280 Å.
3. Supramolecular features
Given that there are no classical donor groups, the packing motifs for (I) and (II) are dominated by a variety of non-classical C—H⋯O, C—H⋯N and C—H⋯S, C—H⋯π and π-π- interactions (Tables 1 and 2).
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In (I), it is notable that both C—H groupings adjacent to the cyanide groups [i.e.:C4 (molecule A) and C19 (molecule B) in the 4-positions of the benzene rings] participate in short C—H⋯O interactions to generate separate [110] chains of A and B molecules, both of which feature C(10) chain motifs, with adjacent molecules in the chain related by translation symmetry. We may speculate that these C—H groupings have been `activated' (made more acidic) by being adjacent to the electron-withdrawing cyanide group (Pedireddi & Desiraju, 1992). The chains are cross-linked by C—H⋯N hydrogen bonds: in each case the donor is the methine group [i.e. C7 (molecule A) and C22 (molecule B)] and the acceptor is the cyanide-N atom of the other asymmetric molecule, i.e. A → B and B → A. This results in double chains (Fig. 5) propagating in [110] in which R33(18) loops are apparent. The chains are cross-linked by C—H⋯π interactions, with all the rings (i.e. both thiophene and both benzene rings) acting as acceptors. The shortest centroid–centroid separation between aromatic rings is 3.9895 (10) Å, indicating that any π–π stacking effects in (I) are very weak at best.
The packing for (II) is less `tidy' in the sense that C—H entities belonging to several different groups (benzene ring, methylene group adjacent to the thiophene ring, thiophene ring, methoxy group) act as donors and none of the C—H⋯O links are particularly short. There are molecule A → molecule A, A → B, B → A and B → B links. Perhaps the most notable are a pair of bonds arising from the methylene groups that generate A + B dimers incorporating R22(8) loops, as shown in Fig. 3 above. A number of C—H⋯π interactions are observed, with all the rings acting as acceptors, but there are no aromatic π–π stacking interactions in (II) (shortest centroid–centroid separation > 4.9Å). When the different intermolecular interactions are taken together, a three-dimensional network arises in the crystal of (II).
4. Hirshfeld analysis
Hirshfeld surface fingerprint plots for (I) (Fig. 6) and (II) (Fig. 7) were calculated with CrystalExplorer17 (Turner et al., 2017). The plot for (I) has `wingtip' features that correspond to the short C—H⋯O hydrogen bonds described above, although the wingtips are not as pronounced as those seen for classical hydrogen bonds (compare: McKinnon et al., 2007). In (II), the wingtips are less apparent, presumably reflecting the longer (and weaker) C—H⋯O interactions in this structure, even though there are more of them in (II) than in (I).
When the fingerprint plots for (I) and (II) are decomposed into the separate types of contacts (McKinnon et al., 2007), some interesting differences arise (Table 3): H⋯H contacts represent the highest percentage in both structures, but they are far more significant in (II), representing over half the contact area, some 20% more than in (I). This deficit is largely made up by N⋯H/H⋯N contacts (i.e. the C—H⋯N hydrogen bonds) in (I), which are barely present in (II). The O⋯H/H⋯O contacts are slightly higher in (II) than (I), presumably reflecting that fact that there are many more C—H⋯O bonds in (II) (compare Table 2), although the H⋯O contacts are shorter in (I). The percentages of C⋯H/H⋯C contacts in the two compounds are very similar, whereas C⋯C contacts are insignificant in both structures, which presumably correlates with the very weak π–π stacking described above. Finally, S⋯H/H⋯S contacts are clearly more prominent in (I) although any C—H⋯S bonds in (I) would be regarded as very weak at best (shortest H⋯S separation = 2.95 Å). When the two molecules in the of (I) are compared with each other (Table 3), there is little difference between them and the same applies to (II).
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5. Database survey
A survey of the Cambridge Structural Database (Groom et al., 2016) updated to September 2017 for the common central –CH=N—N(CH3)—C(=O)—CH2– fragment of the title compounds revealed seven matches, viz. ALAHEC (Cardoso et al., 2016b); FOTMUX (Ramírez et al., 2009a); KULREP (Ramírez et al., 2009b); OFEBIL (Cao et al., 2007), and EYUBAD, EYUBEH and EYUBIL: this latter trio of refcodes correspond to the three isomeric (Cardoso et al., 2016a) noted in the Chemical Context section above.
6. Synthesis and crystallization
The appropriate thienyl acetohydrazide derivative (Cardoso et al., 2014) (0.20 g, 1.0 equiv.) was suspended in acetone (5 ml) and potassium carbonate (4.0 equiv.) was added. The reaction mixture was stirred at room temperature for 30 minutes and methyl iodide (4.0 equiv.) was added. The reaction mixture was maintained at 313 K, until TLC indicated the reaction was complete. The mixture was then rotary evaporated to leave a residue, which was dissolved in water (20 ml) and extracted with ethyl acetate (3 × 10 ml). The organic fractions were combined, dried with anhydrous MgSO4, filtered and the solvent evaporated at reduced pressure. The crystals used for the intensity data collections were recrystallized from methanol solution at room temperature to yield colourless plates of (I) and colourless slabs of (II).
(E)-N′-(3-Cyanobenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, (I). Yield: 78%; yellow solid; m.p. 690–692 K. 1H NMR (400 MHz; DMSO) δ: 8.24 (1H; s; N=CH), 8.14 (1H; d; JHH = 7.9 Hz; H-11′), 8.04 (1H; s; H-7′), 7.87 (1H; d; JHH = 7.7 Hz; H-9′), 7.70–7.66 (1H; m; H-10′), 7.36 (1H; dd; JHH = 5.1 and 1.2 Hz; H-5), 6.99–6.98 (1H; m; H-3), 6.96–6.94 (1H; m; H-4) 4.41 (2H; s; CH2), 3.33 (3H; s; N-CH3). 13C NMR (125 MHz; DMSO) δ: 170.9 (C=O), 138.5 (N=CH), 137.0 (C-2), 136.0 (C-6′ and C-9′), 132.8 (C-11′), 131.4 (C-7′), 130.4 (C-10′), 130.0 (C-3), 126.7 (C-4), 125.2 (C-5), 118.5 (CN), 111.9 (C-8′), 34.3 (N—CH3), 28.1 (CH2). MS/ESI: [M + Na]: 306. IR νmax (cm−1; KBr pellets): 1678 (C=O); 3101 (N—CH3).
(E)-N′-(4-Methoxybenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, (II). Yield: 62%; yellow solid; m.p. 629–630 K. 1H NMR (400 MHz; DMSO) δ: 7.94 (1H; s; N=CH), 7.76 (2H; d; JHH = 8.6; H-7′ and H-11′), 7.34 (1H; d; JHH = 4.8 Hz; H-5), 7.03 (2H; d; JHH = 8.6 Hz; H-9′ and H-8′ and H-10′), 6.97–6.93 (2H; m; H-3 and H-4), 4.34 (2H; s; CH2), 3.81 (3H; s; OCH3) 3.33 (3H; s; N-CH3). 13C NMR (125 MHz; DMSO) δ: 170.4 (C=O), 160.5 (C-9′), 140.4 (N=CH), 137.2 (C-2), 128.6 (C-7′ and C-11′), 127.3 (C-3), 126.5 (C-6′), 126.4 (C-4), 125.0 (C-5), 114.2 (C-8′ and C-10′), 55.2 (OCH3), 34.3 (N—CH3), 27.8 (CH2). MS/ESI: [M + Na]: 299. IR νmax (cm−1; KBr pellet): 1668 (C=O); 2962 (N—CH3).
7. Refinement
Crystal data, data collection and structure . The hydrogen atoms were geometrically placed (C—H = 0.95–1.00 Å) and refined as riding atoms. The constraint Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl carrier) was applied in all cases. The N-methyl group was allowed to rotate, but not to tip, to best fit the electron density (AFIX 137 instruction): in every case this group rotated from its initial orientation to minimize steric interaction with H7; the final orientation leads to a rather short C8—H⋯O1 intramolecular contact but we do not regard this as a bond. The thiophene rings in both molecules of (II) show `flip' rotational disorder.
details are summarized in Table 4
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Supporting information
https://doi.org/10.1107/S2056989017014384/vm2205sup1.cif
contains datablocks I, II, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017014384/vm2205Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989017014384/vm2205IIsup3.hkl
For both structures, data collection: CrystalClear (Rigaku, 2012); cell
CrystalClear (Rigaku, 2012); data reduction: CrystalClear (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015) for (I); SHELXL2014 (Sheldrick, 2015) for (II). For both structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).C15H13N3OS | Z = 4 |
Mr = 283.34 | F(000) = 592 |
Triclinic, P1 | Dx = 1.385 Mg m−3 |
a = 9.3594 (7) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 10.1143 (7) Å | Cell parameters from 15155 reflections |
c = 15.8070 (12) Å | θ = 2.2–27.5° |
α = 106.704 (5)° | µ = 0.24 mm−1 |
β = 92.432 (7)° | T = 100 K |
γ = 106.777 (5)° | Plate, colourless |
V = 1359.31 (18) Å3 | 0.18 × 0.12 × 0.03 mm |
Rigaku Mercury CCD diffractometer | 5204 reflections with I > 2σ(I) |
ω scans | Rint = 0.034 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2012) | θmax = 27.5°, θmin = 2.6° |
Tmin = 0.786, Tmax = 1.000 | h = −11→12 |
18105 measured reflections | k = −12→13 |
6217 independent reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.4808P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6217 reflections | Δρmax = 0.51 e Å−3 |
363 parameters | Δρmin = −0.32 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 | 0.44883 (17) | 0.46449 (16) | 0.16930 (10) | 0.0182 (3) | |
C2 | 0.44634 (18) | 0.57507 (16) | 0.24628 (10) | 0.0198 (3) | |
H2 | 0.3740 | 0.5550 | 0.2851 | 0.024* | |
C3 | 0.54885 (18) | 0.71367 (16) | 0.26619 (10) | 0.0196 (3) | |
H3 | 0.5453 | 0.7879 | 0.3182 | 0.024* | |
C4 | 0.65642 (18) | 0.74502 (16) | 0.21093 (10) | 0.0207 (3) | |
H4 | 0.7269 | 0.8397 | 0.2250 | 0.025* | |
C5 | 0.65933 (17) | 0.63477 (16) | 0.13419 (10) | 0.0183 (3) | |
C6 | 0.55554 (17) | 0.49516 (16) | 0.11306 (10) | 0.0180 (3) | |
H6 | 0.5579 | 0.4215 | 0.0604 | 0.022* | |
C7 | 0.34349 (17) | 0.31634 (16) | 0.14643 (10) | 0.0187 (3) | |
H7 | 0.3492 | 0.2430 | 0.0946 | 0.022* | |
C8 | 0.15716 (19) | 0.03219 (16) | 0.09561 (10) | 0.0227 (3) | |
H8A | 0.1446 | 0.0603 | 0.0421 | 0.034* | |
H8B | 0.0780 | −0.0588 | 0.0904 | 0.034* | |
H8C | 0.2560 | 0.0183 | 0.1018 | 0.034* | |
C9 | 0.04341 (17) | 0.11622 (16) | 0.23031 (10) | 0.0202 (3) | |
C10 | 0.03819 (17) | 0.24178 (16) | 0.30984 (10) | 0.0196 (3) | |
H10A | 0.0702 | 0.3332 | 0.2944 | 0.024* | |
H10B | −0.0668 | 0.2255 | 0.3230 | 0.024* | |
C11 | 0.13786 (17) | 0.25767 (15) | 0.39154 (10) | 0.0182 (3) | |
C12 | 0.09228 (19) | 0.22118 (17) | 0.46509 (10) | 0.0228 (3) | |
H12 | −0.0103 | 0.1799 | 0.4709 | 0.027* | |
C13 | 0.2143 (2) | 0.25137 (18) | 0.53227 (11) | 0.0260 (3) | |
H13 | 0.2019 | 0.2329 | 0.5876 | 0.031* | |
C14 | 0.35045 (19) | 0.30956 (17) | 0.50833 (11) | 0.0251 (3) | |
H14 | 0.4440 | 0.3371 | 0.5449 | 0.030* | |
C15 | 0.77123 (18) | 0.66406 (16) | 0.07614 (10) | 0.0201 (3) | |
N1 | 0.24352 (14) | 0.28688 (13) | 0.19727 (8) | 0.0185 (3) | |
N2 | 0.14646 (15) | 0.14648 (13) | 0.17394 (8) | 0.0194 (3) | |
N3 | 0.86018 (16) | 0.68439 (14) | 0.02951 (9) | 0.0244 (3) | |
O1 | −0.04085 (14) | −0.00766 (12) | 0.21693 (8) | 0.0268 (3) | |
S1 | 0.33237 (4) | 0.32713 (4) | 0.40385 (3) | 0.02304 (10) | |
C16 | 0.12951 (17) | 0.59905 (16) | 0.81831 (10) | 0.0178 (3) | |
C17 | 0.19830 (17) | 0.55084 (16) | 0.74397 (10) | 0.0193 (3) | |
H17 | 0.1600 | 0.4524 | 0.7071 | 0.023* | |
C18 | 0.32126 (17) | 0.64447 (16) | 0.72338 (10) | 0.0199 (3) | |
H18 | 0.3666 | 0.6096 | 0.6726 | 0.024* | |
C19 | 0.37944 (18) | 0.78915 (17) | 0.77615 (10) | 0.0212 (3) | |
H19 | 0.4638 | 0.8534 | 0.7617 | 0.025* | |
C20 | 0.31126 (18) | 0.83843 (16) | 0.85109 (10) | 0.0204 (3) | |
C21 | 0.18679 (17) | 0.74391 (16) | 0.87227 (10) | 0.0192 (3) | |
H21 | 0.1414 | 0.7782 | 0.9232 | 0.023* | |
C22 | −0.00144 (17) | 0.50111 (16) | 0.84135 (10) | 0.0183 (3) | |
H22 | −0.0419 | 0.5329 | 0.8948 | 0.022* | |
C23 | −0.23822 (18) | 0.31465 (17) | 0.89282 (10) | 0.0212 (3) | |
H23A | −0.1578 | 0.3386 | 0.9417 | 0.032* | |
H23B | −0.3220 | 0.2317 | 0.8951 | 0.032* | |
H23C | −0.2736 | 0.3987 | 0.8988 | 0.032* | |
C24 | −0.24432 (18) | 0.14399 (16) | 0.74387 (10) | 0.0205 (3) | |
C25 | −0.17210 (19) | 0.11278 (16) | 0.65922 (10) | 0.0209 (3) | |
H25A | −0.0613 | 0.1532 | 0.6752 | 0.025* | |
H25B | −0.1977 | 0.0061 | 0.6323 | 0.025* | |
C26 | −0.21947 (17) | 0.17434 (16) | 0.59025 (10) | 0.0189 (3) | |
C27 | −0.30906 (18) | 0.09509 (18) | 0.51024 (11) | 0.0240 (3) | |
H27 | −0.3551 | −0.0073 | 0.4928 | 0.029* | |
C28 | −0.32632 (19) | 0.18168 (19) | 0.45580 (11) | 0.0270 (4) | |
H28 | −0.3847 | 0.1437 | 0.3985 | 0.032* | |
C29 | −0.24891 (19) | 0.32583 (18) | 0.49576 (11) | 0.0248 (3) | |
H29 | −0.2465 | 0.3998 | 0.4694 | 0.030* | |
C30 | 0.37254 (18) | 0.98796 (17) | 0.90659 (11) | 0.0225 (3) | |
N4 | −0.05999 (14) | 0.37105 (13) | 0.78716 (8) | 0.0177 (3) | |
N5 | −0.18037 (15) | 0.27735 (13) | 0.80764 (8) | 0.0193 (3) | |
N6 | 0.42280 (17) | 1.10717 (15) | 0.95097 (9) | 0.0275 (3) | |
O2 | −0.35504 (14) | 0.05496 (12) | 0.75548 (8) | 0.0281 (3) | |
S2 | −0.15679 (5) | 0.35686 (4) | 0.59911 (3) | 0.02189 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0199 (8) | 0.0169 (7) | 0.0193 (7) | 0.0065 (6) | 0.0007 (6) | 0.0074 (6) |
C2 | 0.0208 (8) | 0.0197 (7) | 0.0198 (7) | 0.0069 (6) | 0.0033 (6) | 0.0069 (6) |
C3 | 0.0223 (8) | 0.0176 (7) | 0.0174 (7) | 0.0065 (6) | 0.0021 (6) | 0.0029 (6) |
C4 | 0.0212 (8) | 0.0175 (7) | 0.0223 (8) | 0.0042 (6) | 0.0014 (6) | 0.0068 (6) |
C5 | 0.0192 (8) | 0.0195 (7) | 0.0179 (7) | 0.0068 (6) | 0.0022 (6) | 0.0080 (6) |
C6 | 0.0201 (8) | 0.0179 (7) | 0.0171 (7) | 0.0080 (6) | 0.0015 (6) | 0.0055 (6) |
C7 | 0.0207 (8) | 0.0165 (7) | 0.0175 (7) | 0.0060 (6) | −0.0003 (6) | 0.0035 (6) |
C8 | 0.0276 (9) | 0.0159 (7) | 0.0195 (7) | 0.0028 (6) | 0.0031 (6) | 0.0019 (6) |
C9 | 0.0194 (8) | 0.0189 (7) | 0.0210 (7) | 0.0044 (6) | 0.0000 (6) | 0.0062 (6) |
C10 | 0.0176 (7) | 0.0194 (7) | 0.0223 (7) | 0.0074 (6) | 0.0038 (6) | 0.0057 (6) |
C11 | 0.0172 (7) | 0.0143 (6) | 0.0217 (7) | 0.0062 (6) | 0.0038 (6) | 0.0019 (6) |
C12 | 0.0210 (8) | 0.0266 (8) | 0.0213 (8) | 0.0114 (6) | 0.0076 (6) | 0.0038 (6) |
C13 | 0.0300 (9) | 0.0307 (8) | 0.0177 (7) | 0.0149 (7) | 0.0043 (6) | 0.0028 (6) |
C14 | 0.0246 (8) | 0.0238 (8) | 0.0235 (8) | 0.0101 (6) | −0.0023 (6) | 0.0007 (6) |
C15 | 0.0220 (8) | 0.0161 (7) | 0.0205 (7) | 0.0051 (6) | −0.0003 (6) | 0.0046 (6) |
N1 | 0.0191 (7) | 0.0142 (6) | 0.0205 (6) | 0.0035 (5) | −0.0001 (5) | 0.0049 (5) |
N2 | 0.0218 (7) | 0.0128 (6) | 0.0191 (6) | 0.0022 (5) | 0.0020 (5) | 0.0019 (5) |
N3 | 0.0259 (7) | 0.0223 (7) | 0.0219 (7) | 0.0049 (6) | 0.0046 (6) | 0.0048 (5) |
O1 | 0.0274 (6) | 0.0181 (5) | 0.0268 (6) | −0.0018 (5) | 0.0043 (5) | 0.0038 (5) |
S1 | 0.0175 (2) | 0.02163 (19) | 0.0281 (2) | 0.00403 (15) | 0.00253 (15) | 0.00725 (16) |
C16 | 0.0182 (7) | 0.0169 (7) | 0.0187 (7) | 0.0056 (6) | −0.0002 (6) | 0.0065 (6) |
C17 | 0.0202 (8) | 0.0169 (7) | 0.0201 (7) | 0.0059 (6) | 0.0003 (6) | 0.0052 (6) |
C18 | 0.0206 (8) | 0.0225 (7) | 0.0174 (7) | 0.0080 (6) | 0.0033 (6) | 0.0063 (6) |
C19 | 0.0197 (8) | 0.0216 (7) | 0.0224 (8) | 0.0042 (6) | 0.0005 (6) | 0.0095 (6) |
C20 | 0.0226 (8) | 0.0170 (7) | 0.0201 (7) | 0.0046 (6) | −0.0021 (6) | 0.0060 (6) |
C21 | 0.0206 (8) | 0.0192 (7) | 0.0183 (7) | 0.0060 (6) | 0.0012 (6) | 0.0069 (6) |
C22 | 0.0199 (8) | 0.0185 (7) | 0.0176 (7) | 0.0073 (6) | 0.0027 (6) | 0.0057 (6) |
C23 | 0.0241 (8) | 0.0208 (7) | 0.0185 (7) | 0.0060 (6) | 0.0050 (6) | 0.0063 (6) |
C24 | 0.0241 (8) | 0.0163 (7) | 0.0215 (7) | 0.0064 (6) | 0.0025 (6) | 0.0066 (6) |
C25 | 0.0264 (8) | 0.0146 (7) | 0.0208 (7) | 0.0071 (6) | 0.0045 (6) | 0.0035 (6) |
C26 | 0.0201 (8) | 0.0174 (7) | 0.0194 (7) | 0.0071 (6) | 0.0067 (6) | 0.0044 (6) |
C27 | 0.0212 (8) | 0.0251 (8) | 0.0221 (8) | 0.0049 (6) | 0.0039 (6) | 0.0045 (6) |
C28 | 0.0243 (9) | 0.0352 (9) | 0.0221 (8) | 0.0121 (7) | 0.0015 (6) | 0.0072 (7) |
C29 | 0.0288 (9) | 0.0297 (8) | 0.0211 (8) | 0.0159 (7) | 0.0060 (6) | 0.0089 (6) |
C30 | 0.0235 (8) | 0.0210 (8) | 0.0228 (8) | 0.0041 (6) | 0.0041 (6) | 0.0093 (6) |
N4 | 0.0178 (6) | 0.0165 (6) | 0.0198 (6) | 0.0047 (5) | 0.0031 (5) | 0.0078 (5) |
N5 | 0.0203 (7) | 0.0168 (6) | 0.0201 (6) | 0.0041 (5) | 0.0059 (5) | 0.0063 (5) |
N6 | 0.0310 (8) | 0.0216 (7) | 0.0260 (7) | 0.0038 (6) | 0.0058 (6) | 0.0060 (6) |
O2 | 0.0301 (7) | 0.0188 (5) | 0.0294 (6) | −0.0007 (5) | 0.0063 (5) | 0.0068 (5) |
S2 | 0.0295 (2) | 0.01730 (18) | 0.01936 (19) | 0.00892 (15) | 0.00386 (15) | 0.00484 (14) |
C1—C6 | 1.392 (2) | C16—C17 | 1.396 (2) |
C1—C2 | 1.403 (2) | C16—C21 | 1.397 (2) |
C1—C7 | 1.467 (2) | C16—C22 | 1.470 (2) |
C2—C3 | 1.389 (2) | C17—C18 | 1.381 (2) |
C2—H2 | 0.9500 | C17—H17 | 0.9500 |
C3—C4 | 1.388 (2) | C18—C19 | 1.391 (2) |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C4—C5 | 1.399 (2) | C19—C20 | 1.402 (2) |
C4—H4 | 0.9500 | C19—H19 | 0.9500 |
C5—C6 | 1.400 (2) | C20—C21 | 1.399 (2) |
C5—C15 | 1.444 (2) | C20—C30 | 1.442 (2) |
C6—H6 | 0.9500 | C21—H21 | 0.9500 |
C7—N1 | 1.2848 (19) | C22—N4 | 1.2887 (19) |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C8—N2 | 1.4607 (19) | C23—N5 | 1.4615 (19) |
C8—H8A | 0.9800 | C23—H23A | 0.9800 |
C8—H8B | 0.9800 | C23—H23B | 0.9800 |
C8—H8C | 0.9800 | C23—H23C | 0.9800 |
C9—O1 | 1.2246 (18) | C24—O2 | 1.2210 (19) |
C9—N2 | 1.3702 (19) | C24—N5 | 1.3766 (19) |
C9—C10 | 1.523 (2) | C24—C25 | 1.518 (2) |
C10—C11 | 1.502 (2) | C25—C26 | 1.510 (2) |
C10—H10A | 0.9900 | C25—H25A | 0.9900 |
C10—H10B | 0.9900 | C25—H25B | 0.9900 |
C11—C12 | 1.367 (2) | C26—C27 | 1.373 (2) |
C11—S1 | 1.7316 (16) | C26—S2 | 1.7294 (15) |
C12—C13 | 1.426 (2) | C27—C28 | 1.427 (2) |
C12—H12 | 0.9500 | C27—H27 | 0.9500 |
C13—C14 | 1.360 (2) | C28—C29 | 1.368 (2) |
C13—H13 | 0.9500 | C28—H28 | 0.9500 |
C14—S1 | 1.7175 (17) | C29—S2 | 1.7146 (17) |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C15—N3 | 1.148 (2) | C30—N6 | 1.151 (2) |
N1—N2 | 1.3797 (17) | N4—N5 | 1.3651 (17) |
C6—C1—C2 | 119.22 (14) | C17—C16—C21 | 119.18 (14) |
C6—C1—C7 | 118.67 (13) | C17—C16—C22 | 121.66 (14) |
C2—C1—C7 | 122.10 (14) | C21—C16—C22 | 119.17 (13) |
C3—C2—C1 | 120.46 (14) | C18—C17—C16 | 120.83 (14) |
C3—C2—H2 | 119.8 | C18—C17—H17 | 119.6 |
C1—C2—H2 | 119.8 | C16—C17—H17 | 119.6 |
C4—C3—C2 | 120.75 (14) | C17—C18—C19 | 120.78 (14) |
C4—C3—H3 | 119.6 | C17—C18—H18 | 119.6 |
C2—C3—H3 | 119.6 | C19—C18—H18 | 119.6 |
C3—C4—C5 | 118.88 (14) | C18—C19—C20 | 118.77 (14) |
C3—C4—H4 | 120.6 | C18—C19—H19 | 120.6 |
C5—C4—H4 | 120.6 | C20—C19—H19 | 120.6 |
C4—C5—C6 | 120.80 (14) | C21—C20—C19 | 120.65 (14) |
C4—C5—C15 | 119.99 (13) | C21—C20—C30 | 120.45 (14) |
C6—C5—C15 | 119.21 (13) | C19—C20—C30 | 118.90 (14) |
C1—C6—C5 | 119.88 (14) | C16—C21—C20 | 119.79 (14) |
C1—C6—H6 | 120.1 | C16—C21—H21 | 120.1 |
C5—C6—H6 | 120.1 | C20—C21—H21 | 120.1 |
N1—C7—C1 | 119.32 (13) | N4—C22—C16 | 118.31 (13) |
N1—C7—H7 | 120.3 | N4—C22—H22 | 120.8 |
C1—C7—H7 | 120.3 | C16—C22—H22 | 120.8 |
N2—C8—H8A | 109.5 | N5—C23—H23A | 109.5 |
N2—C8—H8B | 109.5 | N5—C23—H23B | 109.5 |
H8A—C8—H8B | 109.5 | H23A—C23—H23B | 109.5 |
N2—C8—H8C | 109.5 | N5—C23—H23C | 109.5 |
H8A—C8—H8C | 109.5 | H23A—C23—H23C | 109.5 |
H8B—C8—H8C | 109.5 | H23B—C23—H23C | 109.5 |
O1—C9—N2 | 120.86 (14) | O2—C24—N5 | 120.83 (14) |
O1—C9—C10 | 121.55 (14) | O2—C24—C25 | 121.72 (14) |
N2—C9—C10 | 117.60 (13) | N5—C24—C25 | 117.45 (13) |
C11—C10—C9 | 112.24 (12) | C26—C25—C24 | 114.41 (13) |
C11—C10—H10A | 109.2 | C26—C25—H25A | 108.7 |
C9—C10—H10A | 109.2 | C24—C25—H25A | 108.7 |
C11—C10—H10B | 109.2 | C26—C25—H25B | 108.7 |
C9—C10—H10B | 109.2 | C24—C25—H25B | 108.7 |
H10A—C10—H10B | 107.9 | H25A—C25—H25B | 107.6 |
C12—C11—C10 | 126.61 (14) | C27—C26—C25 | 125.78 (14) |
C12—C11—S1 | 110.52 (12) | C27—C26—S2 | 110.37 (12) |
C10—C11—S1 | 122.87 (11) | C25—C26—S2 | 123.74 (11) |
C11—C12—C13 | 113.18 (15) | C26—C27—C28 | 113.37 (15) |
C11—C12—H12 | 123.4 | C26—C27—H27 | 123.3 |
C13—C12—H12 | 123.4 | C28—C27—H27 | 123.3 |
C14—C13—C12 | 112.47 (15) | C29—C28—C27 | 112.07 (15) |
C14—C13—H13 | 123.8 | C29—C28—H28 | 124.0 |
C12—C13—H13 | 123.8 | C27—C28—H28 | 124.0 |
C13—C14—S1 | 111.68 (13) | C28—C29—S2 | 111.79 (12) |
C13—C14—H14 | 124.2 | C28—C29—H29 | 124.1 |
S1—C14—H14 | 124.2 | S2—C29—H29 | 124.1 |
N3—C15—C5 | 178.57 (16) | N6—C30—C20 | 179.34 (19) |
C7—N1—N2 | 117.84 (12) | C22—N4—N5 | 119.44 (13) |
C9—N2—N1 | 116.96 (12) | N4—N5—C24 | 116.38 (12) |
C9—N2—C8 | 120.85 (12) | N4—N5—C23 | 122.32 (12) |
N1—N2—C8 | 122.11 (12) | C24—N5—C23 | 121.30 (13) |
C14—S1—C11 | 92.14 (8) | C29—S2—C26 | 92.39 (8) |
C6—C1—C2—C3 | 0.1 (2) | C21—C16—C17—C18 | −0.2 (2) |
C7—C1—C2—C3 | 179.36 (14) | C22—C16—C17—C18 | −179.99 (14) |
C1—C2—C3—C4 | −0.6 (2) | C16—C17—C18—C19 | −0.1 (2) |
C2—C3—C4—C5 | 0.5 (2) | C17—C18—C19—C20 | 0.3 (2) |
C3—C4—C5—C6 | 0.2 (2) | C18—C19—C20—C21 | −0.2 (2) |
C3—C4—C5—C15 | −179.27 (14) | C18—C19—C20—C30 | 179.21 (14) |
C2—C1—C6—C5 | 0.5 (2) | C17—C16—C21—C20 | 0.2 (2) |
C7—C1—C6—C5 | −178.73 (13) | C22—C16—C21—C20 | −179.92 (14) |
C4—C5—C6—C1 | −0.7 (2) | C19—C20—C21—C16 | −0.1 (2) |
C15—C5—C6—C1 | 178.75 (13) | C30—C20—C21—C16 | −179.44 (14) |
C6—C1—C7—N1 | −179.33 (14) | C17—C16—C22—N4 | −5.5 (2) |
C2—C1—C7—N1 | 1.4 (2) | C21—C16—C22—N4 | 174.70 (14) |
O1—C9—C10—C11 | 87.85 (18) | O2—C24—C25—C26 | 97.62 (18) |
N2—C9—C10—C11 | −91.98 (16) | N5—C24—C25—C26 | −82.29 (18) |
C9—C10—C11—C12 | −106.11 (17) | C24—C25—C26—C27 | −109.77 (17) |
C9—C10—C11—S1 | 73.77 (15) | C24—C25—C26—S2 | 74.51 (17) |
C10—C11—C12—C13 | −179.17 (14) | C25—C26—C27—C28 | −175.81 (14) |
S1—C11—C12—C13 | 0.93 (17) | S2—C26—C27—C28 | 0.39 (18) |
C11—C12—C13—C14 | −0.3 (2) | C26—C27—C28—C29 | 0.0 (2) |
C12—C13—C14—S1 | −0.46 (18) | C27—C28—C29—S2 | −0.47 (18) |
C1—C7—N1—N2 | −179.87 (12) | C16—C22—N4—N5 | 179.09 (13) |
O1—C9—N2—N1 | −175.82 (14) | C22—N4—N5—C24 | 175.30 (13) |
C10—C9—N2—N1 | 4.0 (2) | C22—N4—N5—C23 | −5.4 (2) |
O1—C9—N2—C8 | 0.9 (2) | O2—C24—N5—N4 | −177.92 (14) |
C10—C9—N2—C8 | −179.28 (13) | C25—C24—N5—N4 | 2.0 (2) |
C7—N1—N2—C9 | 178.23 (14) | O2—C24—N5—C23 | 2.7 (2) |
C7—N1—N2—C8 | 1.6 (2) | C25—C24—N5—C23 | −177.35 (13) |
C13—C14—S1—C11 | 0.84 (13) | C28—C29—S2—C26 | 0.59 (13) |
C12—C11—S1—C14 | −1.01 (12) | C27—C26—S2—C29 | −0.55 (12) |
C10—C11—S1—C14 | 179.09 (12) | C25—C26—S2—C29 | 175.74 (13) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C11–C14/S1, C1–C6, C26–C29/S2 and C16–C21 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.95 | 2.31 | 3.1691 (19) | 151 |
C7—H7···N6ii | 0.95 | 2.53 | 3.452 (2) | 164 |
C19—H19···O2i | 0.95 | 2.27 | 3.1980 (19) | 164 |
C22—H22···N3iii | 0.95 | 2.61 | 3.536 (2) | 164 |
C10—H10B···Cg4iv | 0.99 | 2.97 | 3.4724 (18) | 113 |
C12—H12···Cg3 | 0.95 | 2.60 | 3.436 (2) | 147 |
C23—H23C···Cg2iv | 0.98 | 2.90 | 3.5646 (19) | 126 |
C25—H25B···Cg1v | 0.99 | 2.71 | 3.6910 (18) | 169 |
Symmetry codes: (i) x+1, y+1, z; (ii) x, y−1, z−1; (iii) x−1, y, z+1; (iv) −x, −y+1, −z+1; (v) −x, −y, −z+1. |
C15H16N2O2S | Z = 4 |
Mr = 288.36 | F(000) = 608 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
a = 7.2148 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.8307 (5) Å | Cell parameters from 16502 reflections |
c = 24.1120 (17) Å | θ = 2.4–27.5° |
α = 80.025 (6)° | µ = 0.22 mm−1 |
β = 87.601 (7)° | T = 100 K |
γ = 76.097 (6)° | Slab, colourless |
V = 1468.67 (17) Å3 | 0.19 × 0.13 × 0.05 mm |
Rigaku Mercury CCD diffractometer | 5764 reflections with I > 2σ(I) |
ω scans | Rint = 0.038 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2012) | θmax = 27.5°, θmin = 2.4° |
Tmin = 0.820, Tmax = 1.000 | h = −9→9 |
19273 measured reflections | k = −11→11 |
6732 independent reflections | l = −31→30 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0663P)2 + 0.5738P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
6732 reflections | Δρmax = 0.63 e Å−3 |
367 parameters | Δρmin = −0.51 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 | Occ. (<1) | |
C1 | 0.67008 (18) | 0.60106 (16) | −0.02475 (6) | 0.0180 (3) | |
C2 | 0.5794 (2) | 0.75469 (16) | −0.01600 (6) | 0.0203 (3) | |
H2 | 0.5751 | 0.7804 | 0.0208 | 0.024* | |
C3 | 0.4965 (2) | 0.86847 (16) | −0.06029 (6) | 0.0218 (3) | |
H3 | 0.4357 | 0.9720 | −0.0539 | 0.026* | |
C4 | 0.50131 (19) | 0.83212 (16) | −0.11471 (6) | 0.0200 (3) | |
C5 | 0.5850 (2) | 0.67911 (16) | −0.12395 (6) | 0.0203 (3) | |
H5 | 0.5857 | 0.6529 | −0.1606 | 0.024* | |
C6 | 0.66768 (19) | 0.56475 (16) | −0.07866 (6) | 0.0194 (3) | |
H6 | 0.7235 | 0.4600 | −0.0847 | 0.023* | |
C7 | 0.76607 (19) | 0.48091 (16) | 0.02163 (6) | 0.0187 (3) | |
H7 | 0.8145 | 0.3742 | 0.0166 | 0.022* | |
C8 | 0.9558 (2) | 0.24722 (16) | 0.10720 (6) | 0.0214 (3) | |
H8A | 0.8552 | 0.1999 | 0.0968 | 0.032* | |
H8B | 1.0132 | 0.1882 | 0.1430 | 0.032* | |
H8C | 1.0541 | 0.2431 | 0.0778 | 0.032* | |
C9 | 0.8960 (2) | 0.46599 (17) | 0.16159 (6) | 0.0214 (3) | |
C10 | 0.8168 (2) | 0.64228 (17) | 0.16296 (6) | 0.0235 (3) | |
H10A | 0.6984 | 0.6816 | 0.1403 | 0.028* | |
H10B | 0.7852 | 0.6583 | 0.2022 | 0.028* | |
C11 | 0.9622 (2) | 0.73367 (16) | 0.13961 (6) | 0.0208 (3) | |
C12 | 1.13089 (14) | 0.74915 (10) | 0.17678 (4) | 0.0390 (3) | 0.662 (2) |
H12 | 1.1602 | 0.7098 | 0.2154 | 0.047* | 0.662 (2) |
S1A | 1.13089 (14) | 0.74915 (10) | 0.17678 (4) | 0.0390 (3) | 0.338 (2) |
C13 | 1.2333 (2) | 0.84657 (19) | 0.13194 (8) | 0.0360 (4) | |
H13 | 1.3437 | 0.8787 | 0.1407 | 0.043* | |
C14 | 1.1583 (2) | 0.88417 (18) | 0.07941 (8) | 0.0320 (4) | |
H14 | 1.2118 | 0.9443 | 0.0492 | 0.038* | |
C15 | 0.4195 (3) | 0.9248 (2) | −0.21167 (7) | 0.0349 (4) | |
H15A | 0.3625 | 1.0230 | −0.2370 | 0.052* | |
H15B | 0.3453 | 0.8461 | −0.2132 | 0.052* | |
H15C | 0.5512 | 0.8841 | −0.2234 | 0.052* | |
N1 | 0.78323 (16) | 0.52285 (13) | 0.06906 (5) | 0.0181 (2) | |
N2 | 0.87351 (17) | 0.41187 (13) | 0.11301 (5) | 0.0188 (2) | |
O1 | 0.98112 (17) | 0.37640 (13) | 0.20239 (4) | 0.0287 (2) | |
O2 | 0.41861 (15) | 0.95573 (12) | −0.15535 (4) | 0.0257 (2) | |
S1 | 0.96968 (7) | 0.81888 (6) | 0.07181 (2) | 0.02516 (17) | 0.662 (2) |
C12A | 0.96968 (7) | 0.81888 (6) | 0.07181 (2) | 0.02516 (17) | 0.338 (2) |
H12A | 0.8915 | 0.8263 | 0.0402 | 0.030* | 0.338 (2) |
C16 | 0.7764 (2) | 0.37271 (18) | 0.53247 (6) | 0.0232 (3) | |
C17 | 0.8223 (2) | 0.21881 (18) | 0.51957 (6) | 0.0259 (3) | |
H17 | 0.8225 | 0.2045 | 0.4814 | 0.031* | |
C18 | 0.8670 (2) | 0.08863 (18) | 0.56149 (7) | 0.0273 (3) | |
H18 | 0.8965 | −0.0147 | 0.5522 | 0.033* | |
C19 | 0.8691 (2) | 0.10806 (18) | 0.61799 (6) | 0.0246 (3) | |
C20 | 0.8182 (2) | 0.25909 (19) | 0.63179 (6) | 0.0263 (3) | |
H20 | 0.8150 | 0.2731 | 0.6700 | 0.032* | |
C21 | 0.7718 (2) | 0.38993 (18) | 0.58890 (7) | 0.0261 (3) | |
H21 | 0.7363 | 0.4931 | 0.5984 | 0.031* | |
C22 | 0.7391 (2) | 0.51354 (18) | 0.48843 (6) | 0.0246 (3) | |
H22 | 0.6957 | 0.6158 | 0.4983 | 0.030* | |
C23 | 0.6759 (2) | 0.79073 (19) | 0.40919 (7) | 0.0303 (3) | |
H23A | 0.5514 | 0.8036 | 0.4280 | 0.045* | |
H23B | 0.6659 | 0.8684 | 0.3744 | 0.045* | |
H23C | 0.7702 | 0.8073 | 0.4342 | 0.045* | |
C24 | 0.7715 (2) | 0.60876 (19) | 0.34096 (7) | 0.0273 (3) | |
C25 | 0.8229 (2) | 0.43990 (19) | 0.32963 (6) | 0.0269 (3) | |
H25A | 0.8984 | 0.4346 | 0.2945 | 0.032* | |
H25B | 0.9018 | 0.3700 | 0.3609 | 0.032* | |
C26 | 0.6444 (2) | 0.38433 (19) | 0.32416 (7) | 0.0270 (3) | |
C27 | 0.58683 (12) | 0.23749 (10) | 0.36718 (4) | 0.0472 (3) | 0.549 (3) |
H27 | 0.6492 | 0.1698 | 0.3994 | 0.057* | 0.549 (3) |
S2A | 0.58683 (12) | 0.23749 (10) | 0.36718 (4) | 0.0472 (3) | 0.451 (3) |
C28 | 0.3942 (3) | 0.2460 (3) | 0.33734 (10) | 0.0525 (6) | |
H28 | 0.3185 | 0.1725 | 0.3502 | 0.063* | |
C29 | 0.3408 (3) | 0.3617 (3) | 0.29275 (9) | 0.0481 (5) | |
H29 | 0.2236 | 0.3762 | 0.2737 | 0.058* | |
C30 | 0.9352 (3) | −0.0128 (2) | 0.71366 (7) | 0.0395 (4) | |
H30A | 0.9796 | −0.1178 | 0.7365 | 0.059* | |
H30B | 0.8089 | 0.0380 | 0.7268 | 0.059* | |
H30C | 1.0253 | 0.0522 | 0.7172 | 0.059* | |
N3 | 0.76545 (17) | 0.49815 (15) | 0.43654 (5) | 0.0236 (3) | |
N4 | 0.73577 (18) | 0.63152 (15) | 0.39574 (5) | 0.0254 (3) | |
O3 | 0.7577 (2) | 0.72180 (15) | 0.30224 (5) | 0.0378 (3) | |
O4 | 0.92322 (17) | −0.02841 (13) | 0.65599 (5) | 0.0317 (3) | |
S2 | 0.48492 (10) | 0.47394 (10) | 0.27350 (3) | 0.0423 (3) | 0.549 (3) |
C27A | 0.48492 (10) | 0.47394 (10) | 0.27350 (3) | 0.0423 (3) | 0.451 (3) |
H27A | 0.4809 | 0.5607 | 0.2438 | 0.051* | 0.451 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0141 (6) | 0.0180 (6) | 0.0235 (7) | −0.0069 (5) | 0.0000 (5) | −0.0033 (5) |
C2 | 0.0184 (6) | 0.0208 (6) | 0.0234 (7) | −0.0052 (5) | −0.0003 (5) | −0.0073 (5) |
C3 | 0.0185 (6) | 0.0174 (6) | 0.0298 (8) | −0.0027 (5) | −0.0019 (5) | −0.0061 (5) |
C4 | 0.0149 (6) | 0.0189 (6) | 0.0262 (7) | −0.0057 (5) | −0.0022 (5) | −0.0006 (5) |
C5 | 0.0189 (6) | 0.0221 (7) | 0.0215 (7) | −0.0071 (5) | 0.0001 (5) | −0.0045 (5) |
C6 | 0.0176 (6) | 0.0170 (6) | 0.0247 (7) | −0.0054 (5) | 0.0012 (5) | −0.0046 (5) |
C7 | 0.0171 (6) | 0.0163 (6) | 0.0239 (7) | −0.0064 (5) | 0.0015 (5) | −0.0037 (5) |
C8 | 0.0213 (7) | 0.0157 (6) | 0.0276 (7) | −0.0059 (5) | −0.0013 (5) | −0.0022 (5) |
C9 | 0.0230 (7) | 0.0221 (7) | 0.0195 (7) | −0.0085 (5) | 0.0030 (5) | −0.0013 (5) |
C10 | 0.0276 (7) | 0.0225 (7) | 0.0210 (7) | −0.0068 (6) | 0.0047 (5) | −0.0053 (5) |
C11 | 0.0238 (7) | 0.0161 (6) | 0.0224 (7) | −0.0031 (5) | 0.0001 (5) | −0.0047 (5) |
C12 | 0.0445 (6) | 0.0307 (5) | 0.0468 (6) | −0.0145 (4) | 0.0042 (4) | −0.0129 (4) |
S1A | 0.0445 (6) | 0.0307 (5) | 0.0468 (6) | −0.0145 (4) | 0.0042 (4) | −0.0129 (4) |
C13 | 0.0294 (8) | 0.0229 (7) | 0.0597 (12) | −0.0078 (6) | −0.0071 (8) | −0.0141 (7) |
C14 | 0.0331 (8) | 0.0169 (7) | 0.0420 (9) | −0.0014 (6) | 0.0092 (7) | −0.0026 (6) |
C15 | 0.0456 (10) | 0.0298 (8) | 0.0263 (8) | −0.0068 (7) | −0.0088 (7) | 0.0022 (6) |
N1 | 0.0154 (5) | 0.0176 (5) | 0.0213 (6) | −0.0051 (4) | −0.0005 (4) | −0.0012 (4) |
N2 | 0.0196 (6) | 0.0159 (5) | 0.0209 (6) | −0.0053 (4) | −0.0010 (4) | −0.0010 (4) |
O1 | 0.0384 (6) | 0.0264 (5) | 0.0201 (5) | −0.0084 (5) | −0.0030 (4) | 0.0015 (4) |
O2 | 0.0263 (5) | 0.0213 (5) | 0.0265 (5) | −0.0029 (4) | −0.0059 (4) | 0.0011 (4) |
S1 | 0.0214 (3) | 0.0195 (2) | 0.0325 (3) | −0.00284 (18) | 0.00245 (19) | −0.00200 (19) |
C12A | 0.0214 (3) | 0.0195 (2) | 0.0325 (3) | −0.00284 (18) | 0.00245 (19) | −0.00200 (19) |
C16 | 0.0202 (7) | 0.0271 (7) | 0.0231 (7) | −0.0073 (5) | −0.0001 (5) | −0.0036 (6) |
C17 | 0.0260 (7) | 0.0289 (7) | 0.0232 (7) | −0.0057 (6) | 0.0010 (6) | −0.0066 (6) |
C18 | 0.0273 (8) | 0.0247 (7) | 0.0306 (8) | −0.0051 (6) | 0.0006 (6) | −0.0079 (6) |
C19 | 0.0205 (7) | 0.0257 (7) | 0.0269 (8) | −0.0072 (5) | −0.0023 (5) | 0.0008 (6) |
C20 | 0.0280 (8) | 0.0305 (8) | 0.0219 (7) | −0.0093 (6) | −0.0012 (6) | −0.0045 (6) |
C21 | 0.0279 (8) | 0.0238 (7) | 0.0276 (8) | −0.0067 (6) | −0.0010 (6) | −0.0059 (6) |
C22 | 0.0233 (7) | 0.0249 (7) | 0.0262 (7) | −0.0071 (6) | −0.0015 (6) | −0.0033 (6) |
C23 | 0.0324 (8) | 0.0263 (7) | 0.0330 (8) | −0.0101 (6) | −0.0020 (6) | −0.0025 (6) |
C24 | 0.0249 (7) | 0.0348 (8) | 0.0243 (7) | −0.0137 (6) | −0.0049 (6) | −0.0004 (6) |
C25 | 0.0237 (7) | 0.0349 (8) | 0.0224 (7) | −0.0088 (6) | −0.0016 (6) | −0.0024 (6) |
C26 | 0.0248 (7) | 0.0327 (8) | 0.0258 (7) | −0.0075 (6) | −0.0005 (6) | −0.0101 (6) |
C27 | 0.0372 (5) | 0.0359 (4) | 0.0734 (7) | −0.0118 (3) | −0.0040 (4) | −0.0176 (4) |
S2A | 0.0372 (5) | 0.0359 (4) | 0.0734 (7) | −0.0118 (3) | −0.0040 (4) | −0.0176 (4) |
C28 | 0.0597 (13) | 0.0571 (13) | 0.0596 (13) | −0.0358 (11) | 0.0136 (11) | −0.0336 (11) |
C29 | 0.0273 (9) | 0.0755 (15) | 0.0493 (12) | −0.0116 (9) | 0.0014 (8) | −0.0334 (11) |
C30 | 0.0535 (11) | 0.0371 (9) | 0.0285 (9) | −0.0192 (8) | −0.0129 (8) | 0.0075 (7) |
N3 | 0.0208 (6) | 0.0265 (6) | 0.0237 (6) | −0.0088 (5) | −0.0018 (5) | −0.0002 (5) |
N4 | 0.0261 (6) | 0.0255 (6) | 0.0255 (6) | −0.0102 (5) | −0.0030 (5) | −0.0001 (5) |
O3 | 0.0526 (8) | 0.0360 (6) | 0.0263 (6) | −0.0197 (6) | −0.0046 (5) | 0.0047 (5) |
O4 | 0.0369 (6) | 0.0264 (6) | 0.0304 (6) | −0.0091 (5) | −0.0075 (5) | 0.0030 (4) |
S2 | 0.0266 (4) | 0.0548 (5) | 0.0487 (5) | −0.0044 (3) | −0.0049 (3) | −0.0236 (3) |
C27A | 0.0266 (4) | 0.0548 (5) | 0.0487 (5) | −0.0044 (3) | −0.0049 (3) | −0.0236 (3) |
C1—C6 | 1.3935 (19) | C16—C21 | 1.393 (2) |
C1—C2 | 1.4051 (18) | C16—C17 | 1.405 (2) |
C1—C7 | 1.4686 (19) | C16—C22 | 1.467 (2) |
C2—C3 | 1.379 (2) | C17—C18 | 1.376 (2) |
C2—H2 | 0.9500 | C17—H17 | 0.9500 |
C3—C4 | 1.401 (2) | C18—C19 | 1.403 (2) |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C4—O2 | 1.3687 (17) | C19—O4 | 1.3659 (18) |
C4—C5 | 1.3931 (19) | C19—C20 | 1.390 (2) |
C5—C6 | 1.3970 (19) | C20—C21 | 1.395 (2) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—H21 | 0.9500 |
C7—N1 | 1.2811 (18) | C22—N3 | 1.283 (2) |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C8—N2 | 1.4611 (17) | C23—N4 | 1.457 (2) |
C8—H8A | 0.9800 | C23—H23A | 0.9800 |
C8—H8B | 0.9800 | C23—H23B | 0.9800 |
C8—H8C | 0.9800 | C23—H23C | 0.9800 |
C9—O1 | 1.2322 (18) | C24—O3 | 1.231 (2) |
C9—N2 | 1.3690 (18) | C24—N4 | 1.375 (2) |
C9—C10 | 1.5297 (19) | C24—C25 | 1.517 (2) |
C10—C11 | 1.506 (2) | C25—C26 | 1.502 (2) |
C10—H10A | 0.9900 | C25—H25A | 0.9900 |
C10—H10B | 0.9900 | C25—H25B | 0.9900 |
C11—S1A | 1.5863 (17) | C26—S2A | 1.6389 (19) |
C11—C12 | 1.5863 (17) | C26—C27 | 1.6389 (19) |
C11—C12A | 1.6815 (15) | C26—C27A | 1.6695 (17) |
C11—S1 | 1.6815 (15) | C26—S2 | 1.6695 (17) |
C12—C13 | 1.540 (2) | C27—C28 | 1.571 (2) |
C12—H12 | 0.9500 | C27—H27 | 0.9500 |
S1A—C13 | 1.540 (2) | S2A—C28 | 1.571 (2) |
C13—C14 | 1.354 (3) | C28—C29 | 1.347 (3) |
C13—H13 | 0.9500 | C28—H28 | 0.9500 |
C14—C12A | 1.6288 (19) | C29—C27A | 1.605 (2) |
C14—S1 | 1.6288 (19) | C29—S2 | 1.605 (2) |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C15—O2 | 1.430 (2) | C30—O4 | 1.429 (2) |
C15—H15A | 0.9800 | C30—H30A | 0.9800 |
C15—H15B | 0.9800 | C30—H30B | 0.9800 |
C15—H15C | 0.9800 | C30—H30C | 0.9800 |
N1—N2 | 1.3780 (16) | N3—N4 | 1.3768 (17) |
C12A—H12A | 0.9500 | C27A—H27A | 0.9500 |
C6—C1—C2 | 118.52 (13) | C21—C16—C17 | 118.26 (14) |
C6—C1—C7 | 120.41 (12) | C21—C16—C22 | 119.78 (14) |
C2—C1—C7 | 121.07 (13) | C17—C16—C22 | 121.93 (14) |
C3—C2—C1 | 120.60 (13) | C18—C17—C16 | 120.85 (14) |
C3—C2—H2 | 119.7 | C18—C17—H17 | 119.6 |
C1—C2—H2 | 119.7 | C16—C17—H17 | 119.6 |
C2—C3—C4 | 120.31 (13) | C17—C18—C19 | 120.20 (14) |
C2—C3—H3 | 119.8 | C17—C18—H18 | 119.9 |
C4—C3—H3 | 119.8 | C19—C18—H18 | 119.9 |
O2—C4—C5 | 125.10 (13) | O4—C19—C20 | 124.70 (14) |
O2—C4—C3 | 114.90 (12) | O4—C19—C18 | 115.48 (14) |
C5—C4—C3 | 119.99 (13) | C20—C19—C18 | 119.82 (14) |
C4—C5—C6 | 119.10 (13) | C19—C20—C21 | 119.32 (14) |
C4—C5—H5 | 120.5 | C19—C20—H20 | 120.3 |
C6—C5—H5 | 120.5 | C21—C20—H20 | 120.3 |
C1—C6—C5 | 121.40 (12) | C16—C21—C20 | 121.46 (14) |
C1—C6—H6 | 119.3 | C16—C21—H21 | 119.3 |
C5—C6—H6 | 119.3 | C20—C21—H21 | 119.3 |
N1—C7—C1 | 118.66 (12) | N3—C22—C16 | 119.79 (14) |
N1—C7—H7 | 120.7 | N3—C22—H22 | 120.1 |
C1—C7—H7 | 120.7 | C16—C22—H22 | 120.1 |
N2—C8—H8A | 109.5 | N4—C23—H23A | 109.5 |
N2—C8—H8B | 109.5 | N4—C23—H23B | 109.5 |
H8A—C8—H8B | 109.5 | H23A—C23—H23B | 109.5 |
N2—C8—H8C | 109.5 | N4—C23—H23C | 109.5 |
H8A—C8—H8C | 109.5 | H23A—C23—H23C | 109.5 |
H8B—C8—H8C | 109.5 | H23B—C23—H23C | 109.5 |
O1—C9—N2 | 121.10 (13) | O3—C24—N4 | 121.06 (15) |
O1—C9—C10 | 121.10 (13) | O3—C24—C25 | 121.11 (14) |
N2—C9—C10 | 117.78 (12) | N4—C24—C25 | 117.80 (13) |
C11—C10—C9 | 110.00 (11) | C26—C25—C24 | 109.96 (13) |
C11—C10—H10A | 109.7 | C26—C25—H25A | 109.7 |
C9—C10—H10A | 109.7 | C24—C25—H25A | 109.7 |
C11—C10—H10B | 109.7 | C26—C25—H25B | 109.7 |
C9—C10—H10B | 109.7 | C24—C25—H25B | 109.7 |
H10A—C10—H10B | 108.2 | H25A—C25—H25B | 108.2 |
C10—C11—S1A | 122.26 (11) | C25—C26—S2A | 123.86 (12) |
C10—C11—C12 | 122.26 (11) | C25—C26—C27 | 123.86 (12) |
C10—C11—C12A | 123.80 (11) | C25—C26—C27A | 121.30 (12) |
S1A—C11—C12A | 113.85 (10) | S2A—C26—C27A | 114.82 (10) |
C10—C11—S1 | 123.80 (11) | C25—C26—S2 | 121.30 (12) |
C12—C11—S1 | 113.85 (10) | C27—C26—S2 | 114.82 (10) |
C13—C12—C11 | 99.52 (10) | C28—C27—C26 | 96.38 (12) |
C13—C12—H12 | 130.2 | C28—C27—H27 | 131.8 |
C11—C12—H12 | 130.2 | C26—C27—H27 | 131.8 |
C13—S1A—C11 | 99.52 (10) | C28—S2A—C26 | 96.38 (12) |
C14—C13—C12 | 116.71 (14) | C29—C28—C27 | 117.29 (17) |
C14—C13—S1A | 116.71 (14) | C29—C28—S2A | 117.29 (17) |
C14—C13—H13 | 121.6 | C29—C28—H28 | 121.4 |
C12—C13—H13 | 121.6 | C27—C28—H28 | 121.4 |
C13—C14—C12A | 115.10 (14) | C28—C29—C27A | 116.63 (16) |
C13—C14—S1 | 115.10 (14) | C28—C29—S2 | 116.63 (16) |
C13—C14—H14 | 122.4 | C28—C29—H29 | 121.7 |
S1—C14—H14 | 122.4 | S2—C29—H29 | 121.7 |
O2—C15—H15A | 109.5 | O4—C30—H30A | 109.5 |
O2—C15—H15B | 109.5 | O4—C30—H30B | 109.5 |
H15A—C15—H15B | 109.5 | H30A—C30—H30B | 109.5 |
O2—C15—H15C | 109.5 | O4—C30—H30C | 109.5 |
H15A—C15—H15C | 109.5 | H30A—C30—H30C | 109.5 |
H15B—C15—H15C | 109.5 | H30B—C30—H30C | 109.5 |
C7—N1—N2 | 119.49 (11) | C22—N3—N4 | 119.20 (13) |
C9—N2—N1 | 116.55 (11) | C24—N4—N3 | 116.90 (13) |
C9—N2—C8 | 120.98 (11) | C24—N4—C23 | 120.61 (13) |
N1—N2—C8 | 122.28 (11) | N3—N4—C23 | 122.45 (13) |
C4—O2—C15 | 117.14 (12) | C19—O4—C30 | 117.02 (13) |
C14—S1—C11 | 94.79 (8) | C29—S2—C26 | 94.82 (11) |
C14—C12A—C11 | 94.79 (8) | C29—C27A—C26 | 94.82 (11) |
C14—C12A—H12A | 132.6 | C29—C27A—H27A | 132.6 |
C11—C12A—H12A | 132.6 | C26—C27A—H27A | 132.6 |
C6—C1—C2—C3 | −2.5 (2) | C21—C16—C17—C18 | −1.8 (2) |
C7—C1—C2—C3 | 177.32 (13) | C22—C16—C17—C18 | 176.36 (15) |
C1—C2—C3—C4 | 0.1 (2) | C16—C17—C18—C19 | −0.6 (2) |
C2—C3—C4—O2 | −178.41 (13) | C17—C18—C19—O4 | −177.30 (14) |
C2—C3—C4—C5 | 2.0 (2) | C17—C18—C19—C20 | 2.7 (2) |
O2—C4—C5—C6 | 178.77 (13) | O4—C19—C20—C21 | 177.79 (14) |
C3—C4—C5—C6 | −1.7 (2) | C18—C19—C20—C21 | −2.2 (2) |
C2—C1—C6—C5 | 2.8 (2) | C17—C16—C21—C20 | 2.3 (2) |
C7—C1—C6—C5 | −177.01 (12) | C22—C16—C21—C20 | −175.90 (14) |
C4—C5—C6—C1 | −0.7 (2) | C19—C20—C21—C16 | −0.3 (2) |
C6—C1—C7—N1 | 172.62 (13) | C21—C16—C22—N3 | 171.72 (14) |
C2—C1—C7—N1 | −7.2 (2) | C17—C16—C22—N3 | −6.4 (2) |
O1—C9—C10—C11 | 92.19 (16) | O3—C24—C25—C26 | −93.93 (18) |
N2—C9—C10—C11 | −86.14 (16) | N4—C24—C25—C26 | 84.33 (17) |
C9—C10—C11—S1A | −82.95 (15) | C24—C25—C26—S2A | −116.66 (14) |
C9—C10—C11—C12 | −82.95 (15) | C24—C25—C26—C27 | −116.66 (14) |
C9—C10—C11—C12A | 93.33 (14) | C24—C25—C26—C27A | 61.63 (16) |
C9—C10—C11—S1 | 93.33 (14) | C24—C25—C26—S2 | 61.63 (16) |
C10—C11—C12—C13 | 178.21 (12) | C25—C26—C27—C28 | −179.91 (14) |
S1—C11—C12—C13 | 1.59 (11) | S2—C26—C27—C28 | 1.71 (13) |
C10—C11—S1A—C13 | 178.21 (12) | C25—C26—S2A—C28 | −179.91 (14) |
C12A—C11—S1A—C13 | 1.59 (11) | C27A—C26—S2A—C28 | 1.71 (13) |
C11—C12—C13—C14 | −0.83 (16) | C26—C27—C28—C29 | −2.45 (19) |
C11—S1A—C13—C14 | −0.83 (16) | C26—S2A—C28—C29 | −2.45 (19) |
S1A—C13—C14—C12A | −0.25 (19) | S2A—C28—C29—C27A | 2.5 (2) |
C12—C13—C14—S1 | −0.25 (19) | C27—C28—C29—S2 | 2.5 (2) |
C1—C7—N1—N2 | −179.76 (11) | C16—C22—N3—N4 | −177.97 (13) |
O1—C9—N2—N1 | −177.36 (13) | O3—C24—N4—N3 | −176.37 (14) |
C10—C9—N2—N1 | 0.97 (18) | C25—C24—N4—N3 | 5.4 (2) |
O1—C9—N2—C8 | −2.3 (2) | O3—C24—N4—C23 | 1.5 (2) |
C10—C9—N2—C8 | 176.08 (12) | C25—C24—N4—C23 | −176.75 (13) |
C7—N1—N2—C9 | 176.67 (12) | C22—N3—N4—C24 | 178.08 (13) |
C7—N1—N2—C8 | 1.63 (19) | C22—N3—N4—C23 | 0.2 (2) |
C5—C4—O2—C15 | −0.3 (2) | C20—C19—O4—C30 | −2.7 (2) |
C3—C4—O2—C15 | −179.90 (13) | C18—C19—O4—C30 | 177.30 (15) |
C13—C14—S1—C11 | 1.12 (13) | C28—C29—S2—C26 | −1.01 (18) |
C10—C11—S1—C14 | −178.21 (12) | C25—C26—S2—C29 | −179.06 (14) |
C12—C11—S1—C14 | −1.65 (10) | C27—C26—S2—C29 | −0.63 (12) |
C13—C14—C12A—C11 | 1.12 (13) | C28—C29—C27A—C26 | −1.01 (18) |
C10—C11—C12A—C14 | −178.21 (12) | C25—C26—C27A—C29 | −179.06 (14) |
S1A—C11—C12A—C14 | −1.65 (10) | S2A—C26—C27A—C29 | −0.63 (12) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C11–C14/S1, C1–C6, C26–C29/S2 and C16–C21 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···S1i | 0.95 | 2.87 | 3.7326 (14) | 152 |
C10—H10B···O3 | 0.99 | 2.56 | 3.5366 (19) | 169 |
C13—H13···O2ii | 0.95 | 2.58 | 3.499 (2) | 164 |
C15—H15A···O3iii | 0.98 | 2.50 | 3.478 (2) | 176 |
C25—H25A···O1 | 0.99 | 2.38 | 3.3206 (19) | 157 |
C28—H28···O4iv | 0.95 | 2.42 | 3.307 (2) | 156 |
C29—H29···O1v | 0.95 | 2.50 | 3.422 (2) | 163 |
C30—H30A···O1vi | 0.98 | 2.45 | 3.419 (2) | 168 |
C6—H6···Cg1i | 0.95 | 2.67 | 3.6071 (15) | 169 |
C8—H8C···Cg2i | 0.98 | 2.72 | 3.4831 (16) | 135 |
C21—H21···Cg3vii | 0.95 | 2.90 | 3.6721 (18) | 140 |
C23—H23A···Cg4vii | 0.98 | 2.81 | 3.6560 (16) | 145 |
C23—H23C···Cg4viii | 0.98 | 2.88 | 3.6067 (16) | 131 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y, −z+1; (v) x−1, y, z; (vi) −x+2, −y, −z+1; (vii) −x+1, −y+1, −z+1; (viii) −x+2, −y+1, −z+1. |
Contact type | (I) A | (I) B | (I) | (II) A | (II) B | (II) |
H···H | 30.8 | 35.1 | 33.0 | 51.0 | 53.9 | 52.5 |
C···H/H···C | 27.1 | 25.7 | 26.4 | 23.9 | 22.6 | 23.2 |
O···H/H···O | 8.4 | 9.4 | 8.9 | 13.7 | 14.5 | 14.1 |
N···H/H···N | 16.2 | 14.1 | 15.1 | 2.6 | 2.3 | 2.4 |
C···C | 2.9 | 3.0 | 2.9 | 2.1 | 1.6 | 1.8 |
C···N/N···C | 2.8 | 3.8 | 3.3 | 1.8 | 2.6 | 2.2 |
S···H/H···S | 9.0 | 6.9 | 7.9 | 3.5 | 2.2 | 2.9 |
others | 2.8 | 2.0 | 2.4 | 1.4 | 0.3 | 0.9 |
Acknowledgements
We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.
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