The title compound, an arylsulfonyl glycinyl aryl hydrazone Schiff base, crystallizes with two independent molecules in the asymmetric unit. In the crystal, a series of N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π and slipped parallel π–π interactions link the molecules, forming a three-dimensional structure.
Keywords: crystal structure, p-toluenelsulfonyl, glycinyl, arylhydrazone, hydrogen bonding
Abstract
The title acylhydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent molecules (A and B) in the asymmetric unit. The molecules are bent at the S atom, with C—SO2—NH—CH2 torsion angles of −67.3 (2) and 67.7 (3)° in molecules A and B, respectively. Further, the dihedral angles between the sulfonylglycine segments and the p-toluenesulfonyl rings are 76.1 (1) and 85.8 (1)° in molecules A and B, respectively. The central hydrazone segments and the toluene rings attached to them are almost co-planar with their mean planes being inclined to one another by 5.2 (2) (molecule A) and 2.9 (2)° (molecule B). The dihedral angles between the benzene rings are 86.83 (12) (molecule A) and 74.00 (14)° (molecule B). In the crystal, the A molecules are linked by a pair of N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are linked via three N—H⋯O hydrogen bonds involving the B molecules, forming chains along [100] and enclosing R 2 2(12) and R 4 4(16) ring motifs. The chains are linked via C—H⋯O hydrogen bonds and a C—H⋯π interaction, forming sheets parallel to (010). There is a further C—H⋯π interaction and a slipped parallel π–π interaction [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.
Chemical context
Hydrazones display numerous biological activities. The hydrazone Schiff bases of aroyl, acyl and heteroaroyl compounds are more versatile and flexible (in the sense that they can be used as reaction intermediates in organic synthesis and as ligands forming complexes with metal ions in coordination chemistry) due to the presence of the C=O group, an additional donor site. N-acylhydrazones containing a glycine residue have been investigated extensively for their biological and medical activities (Tian et al., 2011 ▸). Antiviral activity has been shown for acylhydrazone derivatives which contain an amino acid moiety and an electron-donating substituent in the sulfonyl phenyl ring (Tian et al., 2009 ▸). The biological activities of these Schiff bases are thought to be related to structural aspects.
In a continuation of our studies of substituent effects on the structures of such compounds, for example N-(aryl)-amides (Gowda et al., 2006 ▸; Rodrigues et al., 2011 ▸), N-chloroarylamides (Jyothi & Gowda, 2004 ▸) and N-bromoarylsulfonamides (Usha & Gowda, 2006 ▸), we report herein on the synthesis and crystal structure of the title compound. This acylhydrazone derivative contains a glycine moiety and electron-donating substituents in both the sulfonyl and hydrazone aromatic rings.
Structural commentary
The molecular structures of the two independent molecules (A and B) of the title compound are shown in Fig. 1 ▸. It can be seen quite clearly from Fig. 1 ▸ that molecule A has an extended conformation while molecule B is U-shaped. In molecule A, the conformations of the hydrazide N—H and C—H bonds are syn to each other, while the N—H and C=O bonds are anti to each other. On the sulfonamide side, the conformations of the sulfonamide N—H and C=O bonds are syn to each other. In molecule B, the conformations of the hydrazide N—H and C—H bonds, the hydrazide N—H and C=O, and the C=O and sulfonamide N—H bonds are all syn to each other.
Figure 1.
The molecular structure of the two independent molecules of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
In molecule A, the benzene rings are inclined to one another by 86.83 (12)°. The mean plane through atoms C9/N3/N2/C8/O3/C7 [maximum deviation of 0.043 (2) Å for N2], the central section of the molecule, is inclined to the two benzene rings, C1–C6 and C10–C15, by 86.38 (12) and 7.22 (12)°, respectively. In molecule B, the benzene rings (C18–C23 and C27–C32) are inclined to one another by 74.00 (14)°, and by 76.85 (13) and 2.91 (12)°, respectively, to the mean plane through atoms C26/N6/N5/C25/O6/C24 [maximum deviation of 0.061 (2) Å for C26]. The different conformations of molecules A and B are further demonstrated by the differences in the equivalent torsion angles; N1—C7—C8—N2 = 29.3 (3) ° in A, compared to N4—C24—C25—N5 = 177.2 (2)° in B, and C1—S1—N1—C7 = −67.3 (2)° in A, compared to C18—S2—N4—C24 = 67.7 (3)° in B.
The carbonyl bonds lengths, C8—O3 in A and C25—O6 in B, are 1.214 (3) and 1.229 (3) Å, respectively, indicating that the molecules exist in the keto form in the solid state. The C9=N3 and C26=N6 bond lengths, both 1.272 (3) Å in molecules A and B, respectively, confirm their significant double-bond character. The N2—N3 and N5—N6 bond distances are 1.383 (3) and 1.379 (3) Å, respectively, and the C8—N2 and C25—N5 bond distances are 1.339 (3) and 1.334 (3) Å, respectively, which indicates significant delocalization of π-electron density over the hydrazone portions of the molecules.
Supramolecular features
In the crystal, the A molecules are linked by a pair of N—H⋯O hydrogen bonds, forming inversion dimers with an 
(8) ring motif. The dimers are linked via three N—H⋯O hydrogen bonds involving the B molecules, forming chains along [100] that enclose (12) and 
(16) ring motifs (Table 1 ▸ and Fig. 2 ▸). The chains are linked via C—H⋯O hydrogen bonds and a C—H⋯π interaction, forming sheets parallel to (010). The is a C—H⋯π interaction and a slipped parallel π–π interaction [Cg2⋯Cg2i = 3.8773 (16) Å; inter-planar distance = 3.6071 (11) Å; slippage = 1.422 Å; Cg2 is the centroid of ring C10–C15, symmetry code: (i) −x, −y + 1, −z], between the sheets, leading to the formation of a three-dimensional framework (Fig. 3 ▸).
Table 1. Hydrogen-bond geometry (, ).
Cg1 and Cg3 are the centroids of the p-toluenesulfonamide rings C1C6 and C18C23, respectively.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| N1H1NO2i | 0.84(2) | 2.13(2) | 2.947(2) | 162(2) |
| N2H2NO6ii | 0.85(2) | 2.21(2) | 3.047(3) | 169(2) |
| N4H4NO2iii | 0.83(2) | 2.18(2) | 2.965(3) | 157(3) |
| N5H5NO3iv | 0.86(2) | 1.96(2) | 2.809(3) | 169(3) |
| C6H6O6v | 0.93 | 2.55 | 3.305(3) | 139 |
| C7H7AO5v | 0.97 | 2.51 | 3.256(3) | 133 |
| C19H19O4v | 0.93 | 2.57 | 3.212(4) | 127 |
| C14H14Cg1vi | 0.93 | 2.91 | 3.832(3) | 171 |
| C29H29Cg3iv | 0.93 | 2.84 | 3.753(4) | 167 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
; (v) 
; (vi) 
.
Figure 2.
Hydrogen-bonding pattern in the title compound (see Table 1 ▸ for details).
Figure 3.
A view along the b axis of the crystal packing of the title compound. For details of the hydrogen bonds and C—H⋯π interactions (dashed lines), see Table 1 ▸ (molecule A is blue and molecule B is red).
Database survey
A search of the Cambridge Structural Database (Version 5.36; Groom & Allen, 2014 ▸) for the fragment –NH–CH2–C(=O)–NH–N=CH– yielded only one hit, namely N-(2-hydroxy-1-naphthylmethylene)-N′-(N-phenylglycyl)hydrazine (MEMTOO; Gudasi et al., 2006 ▸). We have also very recently reported the crystal structure of a similar compound, namely (E)-N-{2-[2-(3-chlorobenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide monohydrate (Purandara et al., 2015 ▸).
Synthesis and crystallization
p-Toluenesulfonyl chloride (0.01 mol) was added to glycine (0.02 mol) dissolved in an aqueous solution of potassium carbonate (0.06 mol, 50 ml). The reaction mixture was stirred at 373 K for 6 h, left overnight at room temperature, then filtered and treated with dilute hydrochloric acid. The solid N-(p-toluenesulfonyl)glycine (L1) obtained was crystallized from aqueous ethanol.
Sulfuric acid (0.5 ml) was added to L1 (0.02 mol) dissolved in ethanol (30 ml) and the mixture was refluxed. The reaction was monitored by TLC at regular intervals. After completion of the reaction, the reaction mixture was concentrated to remove the excess ethanol. The product, N-(p-toluenesulfonyl)glycine ethyl ester (L2) was poured into water, neutralized with sodium bicarbonate and recrystallized from acetone.
The pure L2 (0.01 mol) was then added in small portions to a stirred solution of 99% hydrazine hydrate (10 ml) in 30 ml ethanol and the mixture was refluxed for 6 h. After cooling to room temperature, the resulting precipitate was filtered, washed with cold water and dried to give N-(p-toluenesulfonyl)glycinyl hydrazide (L3).
A mixture of L3 (0.01 mol) and p-methylbenzaldehyde (0.01 mol) in anhydrous methanol (30 ml) and two drops of glacial acetic acid was refluxed for 8 h. After cooling, the precipitate was collected by vacuum filtration, washed with cold methanol and dried. It was recrystallized to constant melting point from methanol (455–457 K). Prism-like colourless single crystals were grown from a DMF solution by slow evaporation of the solvent. The purity of the compound was checked by TLC and characterized by its IR spectrum. The characteristic absorptions observed are 3286.7, 1678.1, 1606.7, 1323.2 and 1157.3 cm−1 for the stretching bands of N—H, C—O, C—N, S—O asymmetric and S—O symmetric, respectively.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The amino H atoms were located in difference Fourier maps and refined with distance restraints: N—H = 0.86 (2) Å with U iso(H) = 1.2U eq(N). The C-bound H atoms were positioned with idealized geometry and refined using a riding model: C—H = 0.93–0.97 Å with U iso(H) = 1.5U eq(C) for methyl H atoms and 1.2U eq(C) for other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C17H19N3O3S |
| M r | 345.41 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 293 |
| a, b, c () | 11.2595(7), 11.2697(9), 14.538(1) |
| , , () | 70.562(6), 87.330(7), 82.262(6) |
| V (3) | 1723.8(2) |
| Z | 4 |
| Radiation type | Mo K |
| (mm1) | 0.21 |
| Crystal size (mm) | 0.36 0.28 0.24 |
| Data collection | |
| Diffractometer | Oxford Diffraction Xcalibur with a Sapphire CCD detector |
| Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸) |
| T min, T max | 0.929, 0.952 |
| No. of measured, independent and observed [I > 2(I)] reflections | 11371, 6281, 4859 |
| R int | 0.020 |
| (sin /)max (1) | 0.602 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.047, 0.115, 1.07 |
| No. of reflections | 6281 |
| No. of parameters | 449 |
| No. of restraints | 4 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| max, min (e 3) | 0.21, 0.37 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015009330/su5131sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009330/su5131Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015009330/su5131Isup3.cml
CCDC reference: 1401257
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
HP thanks the Department of Science and Technology, Government of India, New Delhi for a research fellowship under its INSPIRE Program. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.
supplementary crystallographic information
Crystal data
| C17H19N3O3S | Z = 4 |
| Mr = 345.41 | F(000) = 728 |
| Triclinic, P1 | Dx = 1.331 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.2595 (7) Å | Cell parameters from 4653 reflections |
| b = 11.2697 (9) Å | θ = 2.5–27.9° |
| c = 14.538 (1) Å | µ = 0.21 mm−1 |
| α = 70.562 (6)° | T = 293 K |
| β = 87.330 (7)° | Prism, colourless |
| γ = 82.262 (6)° | 0.36 × 0.28 × 0.24 mm |
| V = 1723.8 (2) Å3 |
Data collection
| Oxford Diffraction Xcalibur single crystal X-ray diffractometer with a Sapphire CCD detector | 6281 independent reflections |
| Radiation source: fine-focus sealed tube | 4859 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.020 |
| Rotation method data acquisition using ω scans | θmax = 25.4°, θmin = 2.5° |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −13→11 |
| Tmin = 0.929, Tmax = 0.952 | k = −12→13 |
| 11371 measured reflections | l = −17→17 |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0366P)2 + 1.1753P] where P = (Fo2 + 2Fc2)/3 |
| 6281 reflections | (Δ/σ)max = 0.016 |
| 449 parameters | Δρmax = 0.21 e Å−3 |
| 4 restraints | Δρmin = −0.37 e Å−3 |
Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.43117 (5) | −0.17537 (5) | −0.01465 (4) | 0.03681 (15) | |
| O1 | 0.36089 (15) | −0.22646 (16) | −0.06749 (12) | 0.0489 (4) | |
| O2 | 0.51332 (14) | −0.08895 (15) | −0.06644 (12) | 0.0453 (4) | |
| O3 | 0.07623 (16) | −0.07163 (18) | 0.17483 (13) | 0.0594 (5) | |
| N1 | 0.34260 (16) | −0.09801 (18) | 0.04163 (15) | 0.0392 (4) | |
| H1N | 0.381 (2) | −0.053 (2) | 0.0626 (17) | 0.047* | |
| N2 | 0.13018 (17) | 0.04983 (19) | 0.02447 (15) | 0.0434 (5) | |
| H2N | 0.171 (2) | 0.053 (2) | −0.0265 (15) | 0.052* | |
| N3 | 0.04565 (17) | 0.15249 (19) | 0.02068 (15) | 0.0445 (5) | |
| C1 | 0.51424 (19) | −0.3020 (2) | 0.07298 (16) | 0.0355 (5) | |
| C2 | 0.4918 (2) | −0.4252 (2) | 0.09054 (18) | 0.0464 (6) | |
| H2 | 0.4308 | −0.4418 | 0.0573 | 0.056* | |
| C3 | 0.5606 (3) | −0.5233 (2) | 0.15777 (19) | 0.0544 (7) | |
| H3 | 0.5467 | −0.6063 | 0.1686 | 0.065* | |
| C4 | 0.6499 (2) | −0.5007 (3) | 0.20942 (19) | 0.0533 (7) | |
| C5 | 0.6692 (2) | −0.3763 (3) | 0.19142 (19) | 0.0521 (6) | |
| H5 | 0.7286 | −0.3595 | 0.2260 | 0.062* | |
| C6 | 0.6032 (2) | −0.2771 (2) | 0.12386 (17) | 0.0439 (6) | |
| H6 | 0.6180 | −0.1942 | 0.1124 | 0.053* | |
| C7 | 0.2439 (2) | −0.1537 (2) | 0.10092 (18) | 0.0423 (5) | |
| H7A | 0.2721 | −0.2001 | 0.1668 | 0.051* | |
| H7B | 0.2158 | −0.2134 | 0.0745 | 0.051* | |
| C8 | 0.1414 (2) | −0.0541 (2) | 0.10389 (17) | 0.0408 (5) | |
| C9 | 0.0466 (2) | 0.2452 (2) | −0.05851 (19) | 0.0447 (6) | |
| H9 | 0.0995 | 0.2364 | −0.1076 | 0.054* | |
| C10 | −0.0314 (2) | 0.3642 (2) | −0.07566 (18) | 0.0412 (5) | |
| C11 | −0.0239 (2) | 0.4593 (3) | −0.16435 (19) | 0.0540 (7) | |
| H11 | 0.0298 | 0.4452 | −0.2113 | 0.065* | |
| C12 | −0.0944 (3) | 0.5742 (3) | −0.1843 (2) | 0.0599 (7) | |
| H12 | −0.0873 | 0.6366 | −0.2445 | 0.072* | |
| C13 | −0.1752 (2) | 0.5988 (2) | −0.1170 (2) | 0.0505 (6) | |
| C14 | −0.1822 (2) | 0.5038 (3) | −0.0284 (2) | 0.0530 (7) | |
| H14 | −0.2360 | 0.5183 | 0.0183 | 0.064* | |
| C15 | −0.1120 (2) | 0.3886 (2) | −0.00723 (19) | 0.0473 (6) | |
| H15 | −0.1186 | 0.3267 | 0.0533 | 0.057* | |
| C16 | 0.7256 (3) | −0.6088 (3) | 0.2820 (3) | 0.0899 (11) | |
| H16A | 0.7480 | −0.6756 | 0.2549 | 0.135* | |
| H16B | 0.6805 | −0.6403 | 0.3408 | 0.135* | |
| H16C | 0.7964 | −0.5795 | 0.2963 | 0.135* | |
| C17 | −0.2530 (3) | 0.7248 (3) | −0.1391 (3) | 0.0770 (9) | |
| H17A | −0.3310 | 0.7174 | −0.1591 | 0.115* | |
| H17B | −0.2171 | 0.7877 | −0.1906 | 0.115* | |
| H17C | −0.2604 | 0.7494 | −0.0817 | 0.115* | |
| S2 | 0.55311 (6) | 0.09396 (8) | 0.65448 (5) | 0.0589 (2) | |
| O4 | 0.59893 (19) | −0.0024 (2) | 0.61467 (17) | 0.0774 (6) | |
| O5 | 0.63233 (18) | 0.1381 (2) | 0.70615 (17) | 0.0843 (7) | |
| O6 | 0.24349 (16) | 0.07650 (17) | 0.82524 (13) | 0.0546 (5) | |
| N4 | 0.4440 (2) | 0.0538 (3) | 0.72822 (16) | 0.0628 (7) | |
| H4N | 0.460 (3) | 0.035 (3) | 0.7870 (14) | 0.075* | |
| N5 | 0.13783 (18) | −0.0168 (2) | 0.74840 (15) | 0.0457 (5) | |
| H5N | 0.0720 (18) | 0.000 (2) | 0.7769 (18) | 0.055* | |
| N6 | 0.13391 (17) | −0.07035 (18) | 0.67618 (14) | 0.0415 (5) | |
| C18 | 0.4840 (2) | 0.2221 (3) | 0.55871 (19) | 0.0528 (7) | |
| C19 | 0.4764 (3) | 0.2135 (3) | 0.4672 (2) | 0.0648 (8) | |
| H19 | 0.5095 | 0.1401 | 0.4548 | 0.078* | |
| C20 | 0.4195 (3) | 0.3142 (3) | 0.3940 (2) | 0.0727 (9) | |
| H20 | 0.4146 | 0.3073 | 0.3324 | 0.087* | |
| C21 | 0.3698 (3) | 0.4244 (3) | 0.4090 (2) | 0.0680 (8) | |
| C22 | 0.3772 (3) | 0.4304 (3) | 0.5017 (3) | 0.0737 (9) | |
| H22 | 0.3432 | 0.5034 | 0.5142 | 0.088* | |
| C23 | 0.4334 (3) | 0.3316 (3) | 0.5761 (2) | 0.0675 (8) | |
| H23 | 0.4374 | 0.3381 | 0.6379 | 0.081* | |
| C24 | 0.3458 (2) | −0.0013 (3) | 0.70435 (18) | 0.0488 (6) | |
| H24A | 0.3676 | −0.0919 | 0.7187 | 0.059* | |
| H24B | 0.3272 | 0.0366 | 0.6354 | 0.059* | |
| C25 | 0.2387 (2) | 0.0232 (2) | 0.76443 (17) | 0.0423 (5) | |
| C26 | 0.0308 (2) | −0.0913 (2) | 0.65790 (17) | 0.0422 (5) | |
| H26 | −0.0352 | −0.0703 | 0.6928 | 0.051* | |
| C27 | 0.0140 (2) | −0.1478 (2) | 0.58330 (16) | 0.0404 (5) | |
| C28 | −0.0982 (2) | −0.1755 (2) | 0.56938 (18) | 0.0497 (6) | |
| H28 | −0.1627 | −0.1557 | 0.6063 | 0.060* | |
| C29 | −0.1157 (3) | −0.2325 (3) | 0.50103 (19) | 0.0559 (7) | |
| H29 | −0.1916 | −0.2520 | 0.4936 | 0.067* | |
| C30 | −0.0230 (3) | −0.2610 (2) | 0.44395 (19) | 0.0552 (7) | |
| C31 | 0.0883 (2) | −0.2282 (3) | 0.4552 (2) | 0.0566 (7) | |
| H31 | 0.1516 | −0.2437 | 0.4156 | 0.068* | |
| C32 | 0.1069 (2) | −0.1732 (2) | 0.52392 (18) | 0.0489 (6) | |
| H32 | 0.1826 | −0.1528 | 0.5306 | 0.059* | |
| C33 | 0.3084 (4) | 0.5341 (4) | 0.3279 (3) | 0.0983 (12) | |
| H33A | 0.2243 | 0.5456 | 0.3419 | 0.147* | |
| H33B | 0.3195 | 0.5168 | 0.2675 | 0.147* | |
| H33C | 0.3422 | 0.6099 | 0.3226 | 0.147* | |
| C34 | −0.0421 (3) | −0.3240 (3) | 0.3695 (2) | 0.0814 (10) | |
| H34A | −0.1259 | −0.3127 | 0.3547 | 0.122* | |
| H34B | −0.0140 | −0.4130 | 0.3955 | 0.122* | |
| H34C | 0.0016 | −0.2863 | 0.3110 | 0.122* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0365 (3) | 0.0364 (3) | 0.0384 (3) | −0.0033 (2) | −0.0001 (2) | −0.0141 (2) |
| O1 | 0.0531 (10) | 0.0495 (10) | 0.0487 (10) | −0.0065 (8) | −0.0111 (8) | −0.0209 (8) |
| O2 | 0.0442 (9) | 0.0439 (9) | 0.0455 (9) | −0.0082 (7) | 0.0067 (7) | −0.0116 (8) |
| O3 | 0.0507 (11) | 0.0712 (13) | 0.0507 (11) | 0.0006 (9) | 0.0139 (9) | −0.0177 (9) |
| N1 | 0.0318 (10) | 0.0384 (11) | 0.0522 (12) | −0.0059 (8) | 0.0004 (9) | −0.0210 (9) |
| N2 | 0.0390 (11) | 0.0467 (12) | 0.0453 (12) | 0.0019 (9) | 0.0053 (9) | −0.0196 (10) |
| N3 | 0.0360 (11) | 0.0466 (12) | 0.0549 (13) | 0.0007 (9) | −0.0010 (9) | −0.0242 (11) |
| C1 | 0.0361 (12) | 0.0356 (12) | 0.0360 (12) | −0.0014 (9) | 0.0029 (9) | −0.0151 (10) |
| C2 | 0.0530 (15) | 0.0435 (14) | 0.0464 (14) | −0.0078 (12) | −0.0003 (11) | −0.0190 (12) |
| C3 | 0.0699 (18) | 0.0355 (14) | 0.0550 (16) | −0.0044 (13) | 0.0057 (14) | −0.0126 (12) |
| C4 | 0.0507 (15) | 0.0528 (16) | 0.0455 (15) | 0.0076 (13) | 0.0030 (12) | −0.0074 (12) |
| C5 | 0.0432 (14) | 0.0616 (17) | 0.0505 (15) | −0.0024 (12) | −0.0064 (12) | −0.0182 (13) |
| C6 | 0.0420 (13) | 0.0426 (13) | 0.0500 (14) | −0.0041 (11) | −0.0034 (11) | −0.0191 (12) |
| C7 | 0.0374 (12) | 0.0408 (13) | 0.0485 (14) | −0.0068 (10) | 0.0045 (10) | −0.0143 (11) |
| C8 | 0.0343 (12) | 0.0492 (14) | 0.0438 (14) | −0.0076 (11) | 0.0012 (10) | −0.0211 (12) |
| C9 | 0.0383 (13) | 0.0510 (15) | 0.0483 (15) | −0.0034 (11) | 0.0004 (11) | −0.0222 (13) |
| C10 | 0.0340 (12) | 0.0454 (14) | 0.0498 (14) | −0.0044 (10) | −0.0031 (10) | −0.0228 (12) |
| C11 | 0.0540 (16) | 0.0580 (17) | 0.0487 (15) | 0.0035 (13) | 0.0081 (12) | −0.0210 (13) |
| C12 | 0.0679 (18) | 0.0546 (17) | 0.0483 (16) | 0.0043 (14) | 0.0018 (13) | −0.0101 (13) |
| C13 | 0.0474 (15) | 0.0528 (15) | 0.0562 (16) | 0.0019 (12) | −0.0058 (12) | −0.0270 (13) |
| C14 | 0.0457 (15) | 0.0632 (17) | 0.0570 (16) | −0.0037 (13) | 0.0086 (12) | −0.0315 (14) |
| C15 | 0.0458 (14) | 0.0494 (15) | 0.0480 (15) | −0.0073 (12) | 0.0044 (11) | −0.0180 (12) |
| C16 | 0.079 (2) | 0.072 (2) | 0.089 (3) | 0.0150 (18) | −0.0154 (19) | 0.0056 (19) |
| C17 | 0.080 (2) | 0.065 (2) | 0.084 (2) | 0.0192 (17) | −0.0088 (18) | −0.0318 (18) |
| S2 | 0.0454 (4) | 0.0787 (5) | 0.0626 (4) | −0.0215 (4) | 0.0047 (3) | −0.0320 (4) |
| O4 | 0.0655 (13) | 0.0849 (15) | 0.0886 (16) | 0.0003 (11) | 0.0035 (11) | −0.0419 (13) |
| O5 | 0.0582 (13) | 0.1185 (19) | 0.0939 (16) | −0.0379 (13) | −0.0071 (11) | −0.0473 (15) |
| O6 | 0.0592 (11) | 0.0601 (11) | 0.0549 (11) | −0.0050 (9) | −0.0064 (9) | −0.0329 (9) |
| N4 | 0.0575 (14) | 0.0940 (18) | 0.0423 (12) | −0.0346 (13) | −0.0014 (11) | −0.0199 (13) |
| N5 | 0.0391 (11) | 0.0578 (13) | 0.0479 (12) | −0.0048 (10) | 0.0018 (9) | −0.0284 (10) |
| N6 | 0.0429 (11) | 0.0435 (11) | 0.0403 (11) | −0.0059 (9) | −0.0022 (9) | −0.0163 (9) |
| C18 | 0.0505 (15) | 0.0647 (17) | 0.0537 (16) | −0.0263 (13) | 0.0157 (12) | −0.0280 (14) |
| C19 | 0.081 (2) | 0.0655 (19) | 0.0554 (18) | −0.0194 (16) | 0.0181 (15) | −0.0285 (16) |
| C20 | 0.092 (2) | 0.079 (2) | 0.0512 (18) | −0.0248 (19) | 0.0127 (16) | −0.0239 (17) |
| C21 | 0.0654 (19) | 0.070 (2) | 0.070 (2) | −0.0253 (16) | 0.0111 (16) | −0.0209 (17) |
| C22 | 0.075 (2) | 0.067 (2) | 0.089 (2) | −0.0143 (17) | 0.0110 (18) | −0.0383 (19) |
| C23 | 0.074 (2) | 0.080 (2) | 0.0650 (19) | −0.0208 (17) | 0.0095 (16) | −0.0428 (18) |
| C24 | 0.0468 (14) | 0.0583 (16) | 0.0448 (14) | −0.0159 (12) | −0.0002 (11) | −0.0182 (12) |
| C25 | 0.0464 (14) | 0.0392 (13) | 0.0411 (13) | −0.0029 (11) | −0.0050 (10) | −0.0134 (11) |
| C26 | 0.0412 (13) | 0.0427 (13) | 0.0408 (13) | −0.0038 (11) | 0.0006 (10) | −0.0121 (11) |
| C27 | 0.0434 (13) | 0.0367 (12) | 0.0381 (12) | −0.0059 (10) | −0.0056 (10) | −0.0074 (10) |
| C28 | 0.0464 (14) | 0.0575 (16) | 0.0431 (14) | −0.0148 (12) | −0.0003 (11) | −0.0108 (12) |
| C29 | 0.0565 (16) | 0.0613 (17) | 0.0511 (16) | −0.0252 (14) | −0.0086 (13) | −0.0123 (13) |
| C30 | 0.0702 (18) | 0.0483 (15) | 0.0493 (15) | −0.0094 (13) | −0.0121 (14) | −0.0167 (13) |
| C31 | 0.0550 (16) | 0.0619 (17) | 0.0578 (17) | 0.0008 (14) | −0.0023 (13) | −0.0292 (14) |
| C32 | 0.0412 (13) | 0.0547 (15) | 0.0542 (15) | −0.0033 (12) | −0.0063 (11) | −0.0228 (13) |
| C33 | 0.098 (3) | 0.089 (3) | 0.098 (3) | −0.007 (2) | −0.008 (2) | −0.018 (2) |
| C34 | 0.104 (3) | 0.081 (2) | 0.074 (2) | −0.017 (2) | −0.0168 (19) | −0.0415 (19) |
Geometric parameters (Å, º)
| S1—O1 | 1.4218 (16) | S2—O4 | 1.421 (2) |
| S1—O2 | 1.4355 (16) | S2—O5 | 1.427 (2) |
| S1—N1 | 1.6090 (19) | S2—N4 | 1.602 (2) |
| S1—C1 | 1.754 (2) | S2—C18 | 1.758 (3) |
| O3—C8 | 1.214 (3) | O6—C25 | 1.229 (3) |
| N1—C7 | 1.453 (3) | N4—C24 | 1.447 (3) |
| N1—H1N | 0.846 (16) | N4—H4N | 0.831 (17) |
| N2—C8 | 1.339 (3) | N5—C25 | 1.334 (3) |
| N2—N3 | 1.383 (3) | N5—N6 | 1.379 (3) |
| N2—H2N | 0.850 (16) | N5—H5N | 0.861 (16) |
| N3—C9 | 1.272 (3) | N6—C26 | 1.272 (3) |
| C1—C2 | 1.382 (3) | C18—C19 | 1.373 (4) |
| C1—C6 | 1.383 (3) | C18—C23 | 1.383 (4) |
| C2—C3 | 1.378 (4) | C19—C20 | 1.376 (4) |
| C2—H2 | 0.9300 | C19—H19 | 0.9300 |
| C3—C4 | 1.380 (4) | C20—C21 | 1.374 (4) |
| C3—H3 | 0.9300 | C20—H20 | 0.9300 |
| C4—C5 | 1.383 (4) | C21—C22 | 1.378 (4) |
| C4—C16 | 1.507 (4) | C21—C33 | 1.508 (5) |
| C5—C6 | 1.372 (3) | C22—C23 | 1.372 (4) |
| C5—H5 | 0.9300 | C22—H22 | 0.9300 |
| C6—H6 | 0.9300 | C23—H23 | 0.9300 |
| C7—C8 | 1.508 (3) | C24—C25 | 1.506 (3) |
| C7—H7A | 0.9700 | C24—H24A | 0.9700 |
| C7—H7B | 0.9700 | C24—H24B | 0.9700 |
| C9—C10 | 1.454 (3) | C26—C27 | 1.459 (3) |
| C9—H9 | 0.9300 | C26—H26 | 0.9300 |
| C10—C11 | 1.383 (3) | C27—C28 | 1.381 (3) |
| C10—C15 | 1.385 (3) | C27—C32 | 1.386 (3) |
| C11—C12 | 1.373 (4) | C28—C29 | 1.384 (4) |
| C11—H11 | 0.9300 | C28—H28 | 0.9300 |
| C12—C13 | 1.375 (4) | C29—C30 | 1.373 (4) |
| C12—H12 | 0.9300 | C29—H29 | 0.9300 |
| C13—C14 | 1.381 (4) | C30—C31 | 1.385 (4) |
| C13—C17 | 1.507 (4) | C30—C34 | 1.515 (4) |
| C14—C15 | 1.373 (3) | C31—C32 | 1.375 (3) |
| C14—H14 | 0.9300 | C31—H31 | 0.9300 |
| C15—H15 | 0.9300 | C32—H32 | 0.9300 |
| C16—H16A | 0.9600 | C33—H33A | 0.9600 |
| C16—H16B | 0.9600 | C33—H33B | 0.9600 |
| C16—H16C | 0.9600 | C33—H33C | 0.9600 |
| C17—H17A | 0.9600 | C34—H34A | 0.9600 |
| C17—H17B | 0.9600 | C34—H34B | 0.9600 |
| C17—H17C | 0.9600 | C34—H34C | 0.9600 |
| O1—S1—O2 | 119.33 (10) | O4—S2—O5 | 119.00 (14) |
| O1—S1—N1 | 108.63 (10) | O4—S2—N4 | 112.07 (14) |
| O2—S1—N1 | 104.92 (10) | O5—S2—N4 | 104.85 (13) |
| O1—S1—C1 | 108.15 (10) | O4—S2—C18 | 107.17 (13) |
| O2—S1—C1 | 107.25 (10) | O5—S2—C18 | 109.91 (14) |
| N1—S1—C1 | 108.09 (10) | N4—S2—C18 | 102.65 (13) |
| C7—N1—S1 | 121.38 (15) | C24—N4—S2 | 122.13 (18) |
| C7—N1—H1N | 117.5 (17) | C24—N4—H4N | 117 (2) |
| S1—N1—H1N | 110.3 (17) | S2—N4—H4N | 115 (2) |
| C8—N2—N3 | 121.0 (2) | C25—N5—N6 | 120.1 (2) |
| C8—N2—H2N | 121.0 (18) | C25—N5—H5N | 120.8 (18) |
| N3—N2—H2N | 117.9 (18) | N6—N5—H5N | 118.5 (18) |
| C9—N3—N2 | 114.1 (2) | C26—N6—N5 | 115.8 (2) |
| C2—C1—C6 | 120.4 (2) | C19—C18—C23 | 119.4 (3) |
| C2—C1—S1 | 120.50 (18) | C19—C18—S2 | 120.7 (2) |
| C6—C1—S1 | 119.12 (17) | C23—C18—S2 | 119.9 (2) |
| C3—C2—C1 | 119.3 (2) | C18—C19—C20 | 119.5 (3) |
| C3—C2—H2 | 120.3 | C18—C19—H19 | 120.2 |
| C1—C2—H2 | 120.3 | C20—C19—H19 | 120.2 |
| C2—C3—C4 | 121.3 (2) | C21—C20—C19 | 122.2 (3) |
| C2—C3—H3 | 119.3 | C21—C20—H20 | 118.9 |
| C4—C3—H3 | 119.3 | C19—C20—H20 | 118.9 |
| C3—C4—C5 | 118.1 (2) | C20—C21—C22 | 117.2 (3) |
| C3—C4—C16 | 120.8 (3) | C20—C21—C33 | 121.6 (3) |
| C5—C4—C16 | 121.0 (3) | C22—C21—C33 | 121.2 (3) |
| C6—C5—C4 | 121.8 (2) | C23—C22—C21 | 121.8 (3) |
| C6—C5—H5 | 119.1 | C23—C22—H22 | 119.1 |
| C4—C5—H5 | 119.1 | C21—C22—H22 | 119.1 |
| C5—C6—C1 | 119.1 (2) | C22—C23—C18 | 119.7 (3) |
| C5—C6—H6 | 120.4 | C22—C23—H23 | 120.1 |
| C1—C6—H6 | 120.4 | C18—C23—H23 | 120.1 |
| N1—C7—C8 | 111.69 (19) | N4—C24—C25 | 108.2 (2) |
| N1—C7—H7A | 109.3 | N4—C24—H24A | 110.1 |
| C8—C7—H7A | 109.3 | C25—C24—H24A | 110.1 |
| N1—C7—H7B | 109.3 | N4—C24—H24B | 110.1 |
| C8—C7—H7B | 109.3 | C25—C24—H24B | 110.1 |
| H7A—C7—H7B | 107.9 | H24A—C24—H24B | 108.4 |
| O3—C8—N2 | 124.9 (2) | O6—C25—N5 | 121.6 (2) |
| O3—C8—C7 | 120.0 (2) | O6—C25—C24 | 122.2 (2) |
| N2—C8—C7 | 115.1 (2) | N5—C25—C24 | 116.2 (2) |
| N3—C9—C10 | 122.9 (2) | N6—C26—C27 | 121.4 (2) |
| N3—C9—H9 | 118.6 | N6—C26—H26 | 119.3 |
| C10—C9—H9 | 118.6 | C27—C26—H26 | 119.3 |
| C11—C10—C15 | 117.9 (2) | C28—C27—C32 | 118.1 (2) |
| C11—C10—C9 | 118.6 (2) | C28—C27—C26 | 119.6 (2) |
| C15—C10—C9 | 123.5 (2) | C32—C27—C26 | 122.3 (2) |
| C12—C11—C10 | 121.2 (2) | C27—C28—C29 | 120.7 (2) |
| C12—C11—H11 | 119.4 | C27—C28—H28 | 119.7 |
| C10—C11—H11 | 119.4 | C29—C28—H28 | 119.7 |
| C11—C12—C13 | 121.3 (3) | C30—C29—C28 | 121.3 (2) |
| C11—C12—H12 | 119.4 | C30—C29—H29 | 119.4 |
| C13—C12—H12 | 119.4 | C28—C29—H29 | 119.4 |
| C12—C13—C14 | 117.5 (2) | C29—C30—C31 | 117.9 (2) |
| C12—C13—C17 | 121.2 (3) | C29—C30—C34 | 121.2 (3) |
| C14—C13—C17 | 121.3 (3) | C31—C30—C34 | 120.8 (3) |
| C15—C14—C13 | 122.0 (2) | C32—C31—C30 | 121.2 (3) |
| C15—C14—H14 | 119.0 | C32—C31—H31 | 119.4 |
| C13—C14—H14 | 119.0 | C30—C31—H31 | 119.4 |
| C14—C15—C10 | 120.2 (2) | C31—C32—C27 | 120.7 (2) |
| C14—C15—H15 | 119.9 | C31—C32—H32 | 119.6 |
| C10—C15—H15 | 119.9 | C27—C32—H32 | 119.6 |
| C4—C16—H16A | 109.5 | C21—C33—H33A | 109.5 |
| C4—C16—H16B | 109.5 | C21—C33—H33B | 109.5 |
| H16A—C16—H16B | 109.5 | H33A—C33—H33B | 109.5 |
| C4—C16—H16C | 109.5 | C21—C33—H33C | 109.5 |
| H16A—C16—H16C | 109.5 | H33A—C33—H33C | 109.5 |
| H16B—C16—H16C | 109.5 | H33B—C33—H33C | 109.5 |
| C13—C17—H17A | 109.5 | C30—C34—H34A | 109.5 |
| C13—C17—H17B | 109.5 | C30—C34—H34B | 109.5 |
| H17A—C17—H17B | 109.5 | H34A—C34—H34B | 109.5 |
| C13—C17—H17C | 109.5 | C30—C34—H34C | 109.5 |
| H17A—C17—H17C | 109.5 | H34A—C34—H34C | 109.5 |
| H17B—C17—H17C | 109.5 | H34B—C34—H34C | 109.5 |
| O1—S1—N1—C7 | 49.8 (2) | O4—S2—N4—C24 | −47.0 (3) |
| O2—S1—N1—C7 | 178.47 (18) | O5—S2—N4—C24 | −177.4 (2) |
| C1—S1—N1—C7 | −67.3 (2) | C18—S2—N4—C24 | 67.7 (3) |
| C8—N2—N3—C9 | 178.9 (2) | C25—N5—N6—C26 | −171.7 (2) |
| O1—S1—C1—C2 | −9.3 (2) | O4—S2—C18—C19 | 3.5 (3) |
| O2—S1—C1—C2 | −139.20 (19) | O5—S2—C18—C19 | 134.1 (2) |
| N1—S1—C1—C2 | 108.2 (2) | N4—S2—C18—C19 | −114.7 (2) |
| O1—S1—C1—C6 | 170.28 (18) | O4—S2—C18—C23 | −178.6 (2) |
| O2—S1—C1—C6 | 40.4 (2) | O5—S2—C18—C23 | −47.9 (3) |
| N1—S1—C1—C6 | −72.3 (2) | N4—S2—C18—C23 | 63.2 (2) |
| C6—C1—C2—C3 | −1.4 (4) | C23—C18—C19—C20 | 0.6 (4) |
| S1—C1—C2—C3 | 178.15 (18) | S2—C18—C19—C20 | 178.6 (2) |
| C1—C2—C3—C4 | 1.4 (4) | C18—C19—C20—C21 | 0.2 (5) |
| C2—C3—C4—C5 | −0.4 (4) | C19—C20—C21—C22 | −0.9 (5) |
| C2—C3—C4—C16 | −179.3 (3) | C19—C20—C21—C33 | 179.6 (3) |
| C3—C4—C5—C6 | −0.6 (4) | C20—C21—C22—C23 | 1.0 (5) |
| C16—C4—C5—C6 | 178.3 (3) | C33—C21—C22—C23 | −179.6 (3) |
| C4—C5—C6—C1 | 0.5 (4) | C21—C22—C23—C18 | −0.2 (5) |
| C2—C1—C6—C5 | 0.5 (3) | C19—C18—C23—C22 | −0.6 (4) |
| S1—C1—C6—C5 | −179.10 (18) | S2—C18—C23—C22 | −178.6 (2) |
| S1—N1—C7—C8 | −151.08 (17) | S2—N4—C24—C25 | −156.3 (2) |
| N3—N2—C8—O3 | 5.1 (4) | N6—N5—C25—O6 | 176.7 (2) |
| N3—N2—C8—C7 | −175.06 (19) | N6—N5—C25—C24 | −3.6 (3) |
| N1—C7—C8—O3 | −150.8 (2) | N4—C24—C25—O6 | −3.1 (3) |
| N1—C7—C8—N2 | 29.3 (3) | N4—C24—C25—N5 | 177.2 (2) |
| N2—N3—C9—C10 | −177.2 (2) | N5—N6—C26—C27 | −179.9 (2) |
| N3—C9—C10—C11 | −179.8 (2) | N6—C26—C27—C28 | 176.4 (2) |
| N3—C9—C10—C15 | 1.2 (4) | N6—C26—C27—C32 | −4.7 (4) |
| C15—C10—C11—C12 | −0.3 (4) | C32—C27—C28—C29 | 3.0 (4) |
| C9—C10—C11—C12 | −179.3 (2) | C26—C27—C28—C29 | −178.1 (2) |
| C10—C11—C12—C13 | −0.2 (4) | C27—C28—C29—C30 | −1.2 (4) |
| C11—C12—C13—C14 | 0.4 (4) | C28—C29—C30—C31 | −1.5 (4) |
| C11—C12—C13—C17 | −179.7 (3) | C28—C29—C30—C34 | 179.7 (3) |
| C12—C13—C14—C15 | −0.2 (4) | C29—C30—C31—C32 | 2.4 (4) |
| C17—C13—C14—C15 | 180.0 (3) | C34—C30—C31—C32 | −178.7 (3) |
| C13—C14—C15—C10 | −0.3 (4) | C30—C31—C32—C27 | −0.6 (4) |
| C11—C10—C15—C14 | 0.5 (4) | C28—C27—C32—C31 | −2.0 (4) |
| C9—C10—C15—C14 | 179.5 (2) | C26—C27—C32—C31 | 179.0 (2) |
Hydrogen-bond geometry (Å, º)
Cg1 and Cg3 are the centroids of the p-toluenesulfonamide rings C1–C6 and C18–C23, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O2i | 0.84 (2) | 2.13 (2) | 2.947 (2) | 162 (2) |
| N2—H2N···O6ii | 0.85 (2) | 2.21 (2) | 3.047 (3) | 169 (2) |
| N4—H4N···O2iii | 0.83 (2) | 2.18 (2) | 2.965 (3) | 157 (3) |
| N5—H5N···O3iv | 0.86 (2) | 1.96 (2) | 2.809 (3) | 169 (3) |
| C6—H6···O6v | 0.93 | 2.55 | 3.305 (3) | 139 |
| C7—H7A···O5v | 0.97 | 2.51 | 3.256 (3) | 133 |
| C19—H19···O4v | 0.93 | 2.57 | 3.212 (4) | 127 |
| C14—H14···Cg1vi | 0.93 | 2.91 | 3.832 (3) | 171 |
| C29—H29···Cg3iv | 0.93 | 2.84 | 3.753 (4) | 167 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y, z−1; (iii) x, y, z+1; (iv) −x, −y, −z+1; (v) −x+1, −y, −z+1; (vi) x−1, y+1, z.
References
- Gowda, B. T., Kozisek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588–594.
- Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]
- Gudasi, K. B., Patil, M. S., Vadavi, R. S., Shenoy, R. V., Patil, S. A. & Nethaji, M. (2006). Transition Met. Chem. 31, 580–585.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015009330/su5131sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009330/su5131Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015009330/su5131Isup3.cml
CCDC reference: 1401257
Additional supporting information: crystallographic information; 3D view; checkCIF report