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The structures of two aryl­sulfonamide para-alk­oxy­chalcones, namely, N-{4-[(E)-3-(4-methoxy­phenyl)prop-2-en­oyl]phenyl}benzene­sulfon­amide, C22H19NO4S, (I), and N-{4-[(E)-3-(4-ethoxy­phenyl)prop-2-en­oyl]phenyl}benzene­sulfon­amide, C23H21NO4S, (II), reveal the effect of the inclusion of one -CH2- group between the CH3 branch and the alk­oxy O atom on the conformation and crystal structure. Although the mol­ecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent mol­ecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C-H...[pi] and [pi]-[pi] inter­actions, while only C-H...[pi] contacts occur in the structure of (II). The role of the additional methyl­ene group in the crystal packing can also be seen in the fact that the alk­oxy O atom is an acceptor in non­classical hydrogen bonds only in the para-eth­oxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N-H...O hydrogen-bonded ribbons, a synthon commonly found in related compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113002291/uk3058sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113002291/uk3058Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113002291/uk3058IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113002291/uk3058Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113002291/uk3058IIsup5.cml
Supplementary material

CCDC references: 934567; 934568

Comment top

Compounds containing a sulfonamide group are well known to possess strong antibacterial effects, some of them being widely used against common bacterial diseases mainly due to their low cost, low toxicity and excellent pharmacological profiles (Ozbek et al., 2007). The sulfonamide group is also present in many biologically active compounds, such as antimicrobial, antithyroid, antitumour and antimalarial drugs (Ozdemir et al., 2009; Seo et al., 2010; Domínguez et al., 2005; Connor, 1998; Hanson et al., 1999). In addition, many substituted aromatic and heterocyclic sulfonamides have been synthesized and their activity against glaucoma has been evaluated (Remko et al., 2010). Chalcones containing an arylsulfonamide group are emerging compounds for which antimalarial properties have been already demonstrated (Domínguez et al., 2005).

As part of our ongoing studies of sulfonamides in terms of their structural features (Martins et al., 2009; Fernandes et al., 2011), in this study, the two title arylsulfonamide para-alkoxychalcones, (I) and (II), differing only in one methylene group in the para-alkoxy group on the chalcone skeleton, were synthesized and their crystal structures determined using single-crystal X-ray diffraction. This molecular difference of only one CH2 group is enough to change the crystal assembly and symmetry. Likewise, the absence of methylene in the para-alkoxy group of (I) is also related to the conformational variability observed in this compound.

Because of the slight molecular structure differences between (I) and (II), they crystallize in different crystal systems and space groups. While the crystal structure of (I) was solved in the centrosymmetric triclinic space group P1, with two independent molecules in the asymmetric unit, (II) crystallizes in the monoclinic space group P21/c with only one molecule in the asymmetric unit (Fig. 1).

Compound (I) has two conformers in its crystal structure, labelled A and B. The chalcone molecular backbones of both conformers are almost completely planar (r.m.s. deviations = 0.0537 and 0.0440 Å, respectively, for conformers A and B, with the greatest deviations being -0.2053 Å for atom C18A or 0.2076 Å for atom C8B, where the chalcone plane is defined by atoms C13–C15/O3 and the C atoms of rings B and C in Fig. 1) and therefore similar, even though there are slight rotations about the sulfamyl S1—N1 and sulfonyl S1—C1 bridging bond axes (Fig. 2). More specifically, the chalcone group of conformer A is more planar than that of conformer B. In the latter, there are three slight rotations on the bond axes of: (i) C10B—C13B, which displaces phenyl ring B from the neighbouring carbonyl group [e.g. the C9B—C10B—C13B—O3B torsion angle is 8.3 (4)°, cf. 5.6 (5)° for the corresponding torsion angle in conformer A); (ii) C15B—C16B, twisting the para-alkoxy-substituted phenyl ring C from the C14C15 group [e.g. the C14B—C15B—C16B—C21B torsion angle is -7.8 (4)°, cf. -0.6 (6)° for the corresponding torsion angle in conformer A]; and (iii) C19B—O4B, setting the methyl group of the methoxy in the para-position out of the phenyl ring C plane [e.g. the C18B—C19B—O4B—C22B torsion angle is 7.8 (4)°, cf. 6.9 (5)° for the corresponding torsion angle in conformer A]. The rotation on this last bond axis is also appreciable in conformer A of (I) and in (II), which also shows a remarkable planarity of its chalcone skeleton (r.m.s. deviation = 0.0371 Å, with the greatest deviation being 0.1563 Å for atom C8), except that the ethyl group is slightly out of the phenyl ring C plane, as mentioned above.

It is interesting to note that in the crystal structure of the only other example of an arylsulfonamide chalcone hybrid found in the Cambridge Structural Database (CSD, Version?; Allen, 2002), namely, 4'-(para-toluenesulfonylamino)-4-hydroxychalcone (TSAHC) (Seo et al., 2010), the chalcone skeleton is strongly twisted, wherein the least-squares planes through the corresponding rings B and C form an angle of 33.9 (8)°. This measurement has values of 10.8 (1), 10.02 (8) and 5.2 (8)° in molecules A and B of (I) and in (II), respectively. In the structure of TSAHC, such a twist may be related to the presence of a further intermolecular classical O—H···O hydrogen bond involving the para-hydroxyl and sulfamyl groups of TSAHC, which does not occur in (I) and (II). However, the N—H···O hydrogen bonding between the amino and carbonyl groups is conserved in the structures of TSAHC, (I) and (II). In all three sulfonamide chalcone derivatives, these N—H···O interactions give rise to infinite one-dimensional ribbons running along the [001] (or [010] in TSAHC) direction (Fig. 3). In the structures of both (I) and (II), each chain has all phenyl rings A always oriented towards the same side of the sulfonamide–chalcone plane (Fig. 3). These ribbons are made up of alternating molecules A and B in (I), while c-glide-related units assemble these supramolecular motifs in (II). The linear ribbons are stacked face-to-face on top of one another, along the b axis in (I) and along the a axis in (II). In contrast, a zigzag chain is formed with 21-screw axis symmetry-related molecules in TSAHC.

In addition to the classical hydrogen bonds, the ribbons in (I) and (II) are supported by C9—H9···O1 hydrogen bonds (Tables 1 and 2). The pairwise interactions co-exist with a degree of coplanarity between sulfonamide–chalcone fragments of the hydrogen-bonded molecules. Between successive molecules along the chain, these fragments, defined as the chalcone plane plus atoms N1 and S1, form dihedral angles of 15.0 and 6.4° in (I) and (II).

Besides the classical hydrogen-bonded assembly of the ribbons of (I) and (II), C9—H9···O1 contacts between the C9—H9 atoms of phenyl ring B as a non-classical hydrogen-bonding donor and a sulfonyl O atom as acceptor also contribute to keeping the molecules of (I) and (II) in contact with the linear N—H···O hydrogen-bonded ribbons. Furthermore, such intermolecular interactions align the sulfonamide–chalcone planes with the ribbons in both structures. However, these planes (the chalcone plane as defined above plus atoms N1 and S1) are aligned with the ribbons in a more planar fashion in (II) than in (I), so that the sulfonamide–chalcone planes of N—H···O hydrogen-bonded molecules form angles of ca 15.0 and 6.4° in (I) and (II), respectively.

The supramolecular assemblies of (I) and (II) are thus similar in the formation of linear ribbons, but the structural similarities between them end there. While the crystal packing of (I) is stabilized by weak C—H···π and ππ interactions, only the former interactions occur in (II). In (I), inversion-related molecules A interact through their CH3 and phenyl A groups in very weak but cooperative C—H···π interactions involving two methyl H atoms [CgA···H22D? = 3.28 Å and CgA···H22E?? = 3.33 Å, where CgA is the centroid calculated through the ring A C atoms of molecule A; symmetry codes: Please provide missing details] (Fig. 4). The phenyl rings of both molecules A and B are further connected by weak ππ interactions in (I), with a CgA···CgA' distance between translation symmetry-related molecules of 3.72 (5) Å (Fig. 4) [Please give details of symmetry code]. However, the CH3 group of the terminal ethoxy group in (II) is involved in C—H···π contacts in this structure and ππ interactions do not occur. The intercalation between the CH3 group of the ethoxy group in (II) leads to the formation of a C23—H23A···CgA interaction [CgA···H23A = 3.04 Å; symmetry code: Please provide missing details], assembling dimers made up of inversion-related molecules (Fig. 5a). In this figure, it is possible to see the occurence of a ππ interaction between the π-electrons of the double bond between the atoms C14 and C15 and the ring B C atoms [CgD···CgBv = 3.56 Å, where CgD is the centroid calculated through atoms C14 and C15, and CgB is the centroid calculated through the ring B C atoms; symmetry code: (v) -x+1, -y, -z+2]. In this structure, the role of the additional methylene group in the crystal packing and symmetry can be also seen in the fact that the alkoxy atom O4 is involved as an acceptor in weak bifurcated non-classical hydrogen bonds, having as donors the neighbouring C2—H2 and C3—H3 groups of phenyl ring A. Both C2—H2···O4 and C3—H3···O4 contacts occur between 21-screw axis symmetry-related molecules assembled into zigzag chains along the [010] direction (Fig. 5b). These contacts and chains are not observed in (I). In the structure of (I), the methoxy group is involved in non-classical C—H···O hydrogen bonding, C22B—H22A···O2B???, as a donor to an O atom of SO2 in an inversion-related molecule B (Fig. 4) [symmetry code: Please provide missing details].

In conclusion, this study presents an interesting example in which a molecular difference of only one CH2 group in the terminal alkoxy group has altered the crystal packing and symmetry in two otherwise identical compounds. While classical hydrogen-bonding patterns are conserved in both structures investigated here, the combination of weak C—H···O, C—H···π and ππ contacts involving the phenyl heads and alkoxy tails differs, and this is responsible for the changes observed in the conformation and intermolecular architecture of these two chalcone–sulfonamide analogues. From a crystallographic point of view, not only are the crystal systems and space groups different for (I) and (II), but the Z' contents also differ. This reveals that their crystal structures must depend on the intermolecular contact patterns involving the methylene group of the alkoxy substituent.

Related literature top

For related literature, see: Allen (2002); Connor (1998); Domínguez et al. (2005); Fernandes et al. (2011); Hanson et al. (1999); Martins et al. (2009); Ozbek et al. (2007); Ozdemir et al. (2009); Remko et al. (2010); Seo et al. (2010).

Experimental top

Compounds (I) and (II) were synthesized by Claisen–Schmidt condensation from N-(4-acetylphenyl)benzenesulfonamide with either p-methoxybenzene [compound (I)] or p-etoxybenzaldehyde [compound (II)], using sodium hydroxide in ethanol (50% w/w) as catalyst. The reactions were performed at 343 K for about either 22 [compound (I)] or 24 [compound (II)] h. In each case, the precipitate was re-crystallized from suitable solvents [Which solvent for each?] to obtain single crystals. The reaction yields were 57 and 65% for (I) and (II), respectively. Their melting point ranges were 446–448 K and 425–427 K, respectively.

Refinement top

All C-bound H atoms were placed geometrically and refined using a riding model, with C—H = 0.97 (CH2), 0.96 (CH3) or 0.93 Å (aromatic groups), and with Uiso(H) = 1.2Ueq(C). Atom H1 bonded to N was found in a difference Fourier map and its positional parameters were refined freely; Uiso(H) = 1.2Ueq(N)

Computing details top

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecular structures of (a) (I) and (b) (II), showing the atom- and ring-labelling schemes. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A superposition of the conformers A (grey) and B (black) of (I). H atoms have been omitted for clarity.
[Figure 3] Fig. 3. (a) The infinite one-dimensional chains of (I), growing along the [001] direction, (b) the stacking of the chains of (I), (c) the infinite one-dimensional chains of (II), growing along the [001] direction, and (d) the stacking of the chains of (II). Classical N—H···O and non-classical C—H···O hydrogen-bonding interactions are shown as dashed lines. [Symmetry codes: (a) (i) -x + 1, -y + 1, -z; (ii), -x + 1, -y + 1, -z + 1; (b) (i) x, -y + 1/2, z - 1/2; (ii) x, -y + 1/2, z + 1/2].
[Figure 4] Fig. 4. The C—H···O, C—H···π and ππ interactions (dashed lines) in the structure of (I). [Symmetry codes: (iii) -x, -y + 1, -z; (iv) x, y - 1, z + 1; (v) -x, -y + 1, -z + 2].
[Figure 5] Fig. 5. (a) The C—H···π interaction and (b) the bifurcated C—H···O hydrogen-bonding contacts in the structure of (II). These interactions are shown as dashed lines. [Symmetry codes: (iii) -x + 1, -y, -z + 2; (iv) -x + 1, y + 1/2, -z + 3/2].
(I) N-{4-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide top
Crystal data top
C22H19NO4SZ = 4
Mr = 393.44F(000) = 824
Triclinic, P1Dx = 1.341 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 11.8650 (3) ÅCell parameters from 6621 reflections
b = 12.2420 (3) Åθ = 2.4–22.8°
c = 14.7287 (3) ŵ = 0.19 mm1
α = 68.075 (1)°T = 298 K
β = 81.665 (1)°Prism, yellow
γ = 80.437 (1)°0.28 × 0.15 × 0.08 mm
V = 1948.99 (8) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
5268 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 9 pixels mm-1θmax = 26.9°, θmin = 1.5°
CCD scansh = 1514
22723 measured reflectionsk = 1415
8378 independent reflectionsl = 1817
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.7349P]
where P = (Fo2 + 2Fc2)/3
8378 reflections(Δ/σ)max < 0.001
512 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C22H19NO4Sγ = 80.437 (1)°
Mr = 393.44V = 1948.99 (8) Å3
Triclinic, P1Z = 4
a = 11.8650 (3) ÅMo Kα radiation
b = 12.2420 (3) ŵ = 0.19 mm1
c = 14.7287 (3) ÅT = 298 K
α = 68.075 (1)°0.28 × 0.15 × 0.08 mm
β = 81.665 (1)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
5268 reflections with I > 2σ(I)
22723 measured reflectionsRint = 0.039
8378 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å3
8378 reflectionsΔρmin = 0.27 e Å3
512 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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) top
xyzUiso*/Ueq
S1A0.17904 (5)0.79421 (6)0.03767 (5)0.0646 (2)
S1B0.36203 (6)0.34197 (7)0.55077 (5)0.0694 (2)
O3B0.52135 (14)0.35404 (17)0.02461 (12)0.0722 (5)
O2B0.25459 (15)0.40900 (18)0.52211 (13)0.0816 (6)
O1B0.41481 (16)0.3584 (2)0.62501 (13)0.0854 (6)
N1A0.24599 (18)0.70776 (19)0.05831 (16)0.0661 (6)
O1A0.21279 (16)0.73965 (17)0.10896 (14)0.0795 (5)
O2A0.05999 (14)0.81540 (18)0.00745 (14)0.0799 (5)
O4B0.05735 (17)0.4984 (2)0.28263 (16)0.0947 (6)
O3A0.31611 (18)0.7139 (2)0.47768 (16)0.1072 (8)
C7B0.4446 (2)0.3629 (2)0.36402 (17)0.0602 (6)
C16B0.2188 (2)0.4344 (2)0.11850 (18)0.0582 (6)
C17B0.2373 (2)0.4527 (2)0.21827 (18)0.0635 (6)
H17B0.31230.44980.24710.076*
N1B0.45667 (19)0.3690 (2)0.45617 (16)0.0751 (7)
C11B0.3353 (2)0.3661 (3)0.23888 (19)0.0766 (8)
H11B0.26420.36870.2180.092*
C7A0.2392 (2)0.7274 (2)0.14772 (18)0.0602 (6)
C21B0.1051 (2)0.4378 (2)0.0777 (2)0.0706 (7)
H21B0.08970.4250.0110.085*
C12B0.3402 (2)0.3639 (3)0.3323 (2)0.0850 (9)
H12B0.27340.36310.37410.102*
C15B0.3171 (2)0.4082 (2)0.06264 (18)0.0601 (6)
H15B0.38790.39880.09710.072*
C18B0.1485 (2)0.4750 (2)0.27569 (19)0.0689 (7)
H18B0.16350.48730.34230.083*
C8B0.5424 (2)0.3574 (2)0.30272 (18)0.0647 (6)
H8B0.61350.35330.32420.078*
C13B0.4309 (2)0.3695 (2)0.07319 (17)0.0565 (6)
C9B0.5370 (2)0.3578 (2)0.21029 (18)0.0630 (6)
H9B0.60460.35350.17030.076*
C1A0.2357 (2)0.9295 (2)0.07958 (17)0.0630 (6)
C10B0.43259 (19)0.3645 (2)0.17527 (17)0.0546 (5)
O4A0.2762 (2)0.9286 (3)0.78912 (19)0.1242 (9)
C14B0.3211 (2)0.3955 (2)0.03014 (18)0.0618 (6)
H14B0.2530.40320.06870.074*
C13A0.2292 (3)0.7493 (3)0.4336 (2)0.0765 (8)
C10A0.2314 (2)0.7464 (2)0.3332 (2)0.0689 (7)
C16A0.0107 (3)0.8190 (2)0.62976 (19)0.0719 (7)
C6A0.1643 (3)1.0319 (3)0.0857 (2)0.0810 (8)
H6A0.08651.02940.06520.097*
C11A0.1398 (2)0.7892 (3)0.2768 (2)0.0840 (9)
H11A0.07350.8260.30070.101*
C21A0.0923 (3)0.8748 (3)0.5895 (2)0.0926 (9)
H21A0.09830.8890.52370.111*
C15A0.1104 (3)0.7821 (3)0.5737 (2)0.0760 (8)
H15A0.17460.74660.60830.091*
C1B0.3442 (3)0.1908 (3)0.58692 (18)0.0731 (7)
C5A0.2092 (3)1.1388 (3)0.1228 (3)0.0997 (10)
H5A0.16131.20890.12830.12*
C19B0.0369 (2)0.4788 (2)0.2336 (2)0.0690 (7)
C12A0.1428 (2)0.7795 (3)0.1863 (2)0.0888 (9)
H12A0.07860.80860.15090.107*
C8A0.3326 (2)0.6855 (3)0.2022 (2)0.0859 (9)
H8A0.39950.65070.17730.103*
C17A0.0138 (3)0.8004 (3)0.7279 (2)0.0867 (9)
H17A0.08080.76270.75750.104*
C18A0.0784 (3)0.8354 (3)0.7838 (2)0.0889 (9)
H18A0.07280.82220.84950.107*
C19A0.1785 (3)0.8901 (3)0.7413 (2)0.0907 (9)
C2A0.3500 (3)0.9334 (3)0.1101 (3)0.0908 (9)
H2A0.3980.8640.10670.109*
C14A0.1232 (3)0.7920 (3)0.4799 (2)0.0790 (8)
H14A0.06150.82770.44210.095*
C22B0.0381 (3)0.5009 (3)0.3814 (3)0.1051 (11)
H22A0.11040.51430.4080.158*
H22B0.00240.42650.3820.158*
H22C0.00670.56380.42030.158*
C20B0.0157 (2)0.4595 (3)0.1338 (2)0.0755 (8)
H20B0.05940.46120.10510.091*
C4A0.3235 (4)1.1419 (3)0.1512 (2)0.0980 (10)
H4A0.35381.21380.17440.118*
C4B0.3128 (6)0.0426 (4)0.6518 (3)0.1318 (15)
H4B0.3020.12220.67340.158*
C3A0.3934 (3)1.0399 (3)0.1455 (3)0.1055 (11)
H3A0.47121.04250.16590.127*
C9A0.3279 (3)0.6945 (3)0.2930 (2)0.0925 (10)
H9A0.39190.66460.32860.111*
C20A0.1851 (3)0.9093 (3)0.6440 (3)0.1008 (10)
H20A0.25280.94590.61510.121*
C6B0.2361 (3)0.1570 (4)0.6157 (2)0.0991 (10)
H6B0.17290.21420.61210.119*
C5B0.2204 (4)0.0392 (5)0.6498 (3)0.1245 (15)
H5B0.14740.01610.67110.149*
C3B0.4211 (5)0.0121 (4)0.6233 (4)0.1494 (19)
H3B0.48340.06980.62510.179*
C2B0.4373 (4)0.1087 (4)0.5910 (3)0.1212 (13)
H2B0.51060.13160.57270.145*
C22A0.2706 (4)0.9231 (4)0.8865 (3)0.1404 (16)
H22D0.3440.9530.91080.211*
H22E0.21360.97040.88650.211*
H22F0.25050.84230.9280.211*
H1B0.521 (4)0.361 (4)0.471 (3)0.169*
H1A0.308 (4)0.679 (4)0.040 (3)0.169*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0553 (4)0.0775 (4)0.0618 (4)0.0065 (3)0.0138 (3)0.0289 (3)
S1B0.0604 (4)0.1005 (5)0.0534 (4)0.0051 (4)0.0090 (3)0.0352 (4)
O3B0.0583 (10)0.0951 (13)0.0643 (11)0.0153 (9)0.0088 (8)0.0392 (10)
O2B0.0657 (11)0.1114 (15)0.0710 (12)0.0104 (10)0.0165 (9)0.0414 (11)
O1B0.0745 (12)0.1324 (17)0.0662 (11)0.0121 (11)0.0132 (9)0.0524 (12)
N1A0.0606 (13)0.0687 (13)0.0635 (13)0.0062 (11)0.0115 (10)0.0211 (11)
O1A0.0751 (12)0.0964 (14)0.0790 (12)0.0091 (10)0.0203 (10)0.0484 (11)
O2A0.0517 (10)0.1042 (15)0.0810 (12)0.0051 (10)0.0121 (9)0.0340 (11)
O4B0.0730 (13)0.1227 (17)0.1015 (16)0.0099 (12)0.0369 (11)0.0536 (14)
O3A0.0757 (14)0.164 (2)0.0926 (15)0.0032 (14)0.0336 (12)0.0555 (15)
C7B0.0583 (14)0.0712 (16)0.0510 (13)0.0083 (12)0.0085 (11)0.0204 (12)
C16B0.0558 (14)0.0639 (15)0.0597 (14)0.0014 (11)0.0119 (11)0.0290 (12)
C17B0.0593 (15)0.0751 (17)0.0599 (15)0.0029 (12)0.0062 (12)0.0305 (13)
N1B0.0599 (13)0.1186 (19)0.0549 (12)0.0170 (13)0.0065 (10)0.0374 (13)
C11B0.0513 (14)0.122 (2)0.0639 (16)0.0070 (15)0.0116 (12)0.0412 (16)
C7A0.0553 (14)0.0580 (14)0.0621 (15)0.0011 (11)0.0114 (12)0.0159 (12)
C21B0.0653 (16)0.0911 (19)0.0630 (16)0.0027 (14)0.0069 (13)0.0411 (15)
C12B0.0521 (15)0.150 (3)0.0620 (16)0.0130 (16)0.0034 (12)0.0483 (18)
C15B0.0570 (14)0.0673 (15)0.0591 (14)0.0024 (12)0.0082 (11)0.0294 (12)
C18B0.0739 (17)0.0772 (17)0.0601 (15)0.0018 (14)0.0158 (13)0.0292 (13)
C8B0.0514 (14)0.0833 (18)0.0603 (15)0.0081 (12)0.0112 (11)0.0246 (13)
C13B0.0575 (14)0.0554 (13)0.0564 (14)0.0043 (11)0.0095 (11)0.0230 (11)
C9B0.0479 (13)0.0803 (17)0.0600 (15)0.0009 (12)0.0055 (11)0.0268 (13)
C1A0.0626 (15)0.0704 (16)0.0516 (13)0.0099 (13)0.0095 (11)0.0226 (12)
C10B0.0537 (13)0.0562 (13)0.0531 (13)0.0010 (11)0.0097 (10)0.0201 (11)
O4A0.126 (2)0.159 (2)0.1018 (18)0.0054 (18)0.0049 (16)0.0699 (17)
C14B0.0543 (14)0.0764 (16)0.0590 (15)0.0043 (12)0.0090 (11)0.0327 (13)
C13A0.0696 (18)0.089 (2)0.0734 (18)0.0095 (15)0.0217 (15)0.0258 (15)
C10A0.0612 (16)0.0761 (17)0.0700 (17)0.0040 (13)0.0155 (13)0.0251 (14)
C16A0.0840 (19)0.0770 (18)0.0593 (15)0.0168 (15)0.0189 (14)0.0223 (14)
C6A0.0802 (19)0.079 (2)0.0747 (19)0.0129 (16)0.0063 (15)0.0275 (16)
C11A0.0661 (17)0.114 (2)0.0673 (17)0.0186 (16)0.0137 (14)0.0364 (17)
C21A0.100 (2)0.120 (3)0.0650 (18)0.002 (2)0.0263 (17)0.0391 (18)
C15A0.0801 (19)0.0826 (19)0.0682 (17)0.0127 (15)0.0256 (15)0.0221 (15)
C1B0.0768 (18)0.093 (2)0.0503 (14)0.0054 (16)0.0095 (13)0.0269 (14)
C5A0.118 (3)0.074 (2)0.092 (2)0.012 (2)0.004 (2)0.0243 (18)
C19B0.0652 (16)0.0740 (17)0.0773 (18)0.0078 (13)0.0270 (14)0.0371 (14)
C12A0.0637 (17)0.127 (3)0.0692 (18)0.0210 (17)0.0213 (14)0.0364 (18)
C8A0.0595 (16)0.114 (2)0.092 (2)0.0184 (16)0.0214 (15)0.0536 (19)
C17A0.097 (2)0.102 (2)0.0659 (18)0.0175 (18)0.0259 (17)0.0260 (17)
C18A0.108 (3)0.108 (2)0.0611 (17)0.028 (2)0.0124 (18)0.0346 (17)
C19A0.103 (3)0.102 (2)0.078 (2)0.021 (2)0.0070 (19)0.0424 (19)
C2A0.0691 (19)0.074 (2)0.116 (3)0.0040 (16)0.0033 (17)0.0263 (18)
C14A0.0752 (19)0.098 (2)0.0655 (17)0.0035 (16)0.0215 (14)0.0293 (16)
C22B0.099 (2)0.136 (3)0.099 (2)0.002 (2)0.050 (2)0.055 (2)
C20B0.0546 (15)0.101 (2)0.0814 (19)0.0029 (14)0.0103 (13)0.0483 (17)
C4A0.121 (3)0.078 (2)0.085 (2)0.014 (2)0.002 (2)0.0197 (17)
C4B0.179 (5)0.113 (3)0.105 (3)0.033 (4)0.019 (3)0.032 (3)
C3A0.084 (2)0.092 (2)0.124 (3)0.010 (2)0.003 (2)0.025 (2)
C9A0.0646 (18)0.129 (3)0.094 (2)0.0162 (18)0.0349 (16)0.053 (2)
C20A0.089 (2)0.133 (3)0.087 (2)0.006 (2)0.0235 (18)0.050 (2)
C6B0.089 (2)0.116 (3)0.090 (2)0.019 (2)0.0312 (18)0.024 (2)
C5B0.132 (4)0.127 (4)0.109 (3)0.046 (3)0.045 (3)0.011 (3)
C3B0.167 (5)0.107 (4)0.137 (4)0.012 (3)0.030 (3)0.029 (3)
C2B0.111 (3)0.110 (3)0.117 (3)0.000 (2)0.026 (2)0.030 (2)
C22A0.186 (5)0.159 (4)0.090 (3)0.029 (3)0.015 (3)0.067 (3)
Geometric parameters (Å, º) top
S1A—O1A1.4220 (18)C10A—C9A1.381 (4)
S1A—O2A1.4293 (17)C16A—C17A1.381 (4)
S1A—N1A1.637 (2)C16A—C21A1.393 (4)
S1A—C1A1.749 (3)C16A—C15A1.451 (4)
S1B—O2B1.4235 (19)C6A—C5A1.382 (4)
S1B—O1B1.4258 (18)C6A—H6A0.93
S1B—N1B1.624 (2)C11A—C12A1.377 (4)
S1B—C1B1.764 (3)C11A—H11A0.93
O3B—C13B1.229 (3)C21A—C20A1.371 (4)
N1A—C7A1.414 (3)C21A—H21A0.93
N1A—H1A0.82 (4)C15A—C14A1.330 (4)
O4B—C19B1.359 (3)C15A—H15A0.93
O4B—C22B1.428 (4)C1B—C2B1.356 (4)
O3A—C13A1.228 (3)C1B—C6B1.373 (4)
C7B—C8B1.372 (3)C5A—C4A1.362 (5)
C7B—C12B1.382 (3)C5A—H5A0.93
C7B—N1B1.416 (3)C19B—C20B1.389 (4)
C16B—C17B1.391 (3)C12A—H12A0.93
C16B—C21B1.396 (3)C8A—C9A1.375 (4)
C16B—C15B1.447 (3)C8A—H8A0.93
C17B—C18B1.375 (3)C17A—C18A1.381 (4)
C17B—H17B0.93C17A—H17A0.93
N1B—H1B0.80 (4)C18A—C19A1.374 (4)
C11B—C12B1.376 (4)C18A—H18A0.93
C11B—C10B1.380 (3)C19A—C20A1.374 (4)
C11B—H11B0.93C2A—C3A1.369 (4)
C7A—C12A1.371 (4)C2A—H2A0.93
C7A—C8A1.377 (3)C14A—H14A0.93
C21B—C20B1.370 (4)C22B—H22A0.96
C21B—H21B0.93C22B—H22B0.96
C12B—H12B0.93C22B—H22C0.96
C15B—C14B1.323 (3)C20B—H20B0.93
C15B—H15B0.93C4A—C3A1.361 (5)
C18B—C19B1.379 (4)C4A—H4A0.93
C18B—H18B0.93C4B—C5B1.351 (6)
C8B—C9B1.370 (3)C4B—C3B1.362 (6)
C8B—H8B0.93C4B—H4B0.93
C13B—C14B1.467 (3)C3A—H3A0.93
C13B—C10B1.485 (3)C9A—H9A0.93
C9B—C10B1.389 (3)C20A—H20A0.93
C9B—H9B0.93C6B—C5B1.374 (5)
C1A—C2A1.368 (4)C6B—H6B0.93
C1A—C6A1.372 (4)C5B—H5B0.93
O4A—C19A1.375 (4)C3B—C2B1.411 (6)
O4A—C22A1.421 (4)C3B—H3B0.93
C14B—H14B0.93C2B—H2B0.93
C13A—C14A1.456 (4)C22A—H22D0.96
C13A—C10A1.489 (4)C22A—H22E0.96
C10A—C11A1.376 (4)C22A—H22F0.96
O1A—S1A—O2A119.61 (12)C12A—C11A—H11A118.8
O1A—S1A—N1A104.80 (11)C20A—C21A—C16A121.9 (3)
O2A—S1A—N1A109.01 (11)C20A—C21A—H21A119
O1A—S1A—C1A108.43 (12)C16A—C21A—H21A119
O2A—S1A—C1A107.90 (12)C14A—C15A—C16A129.1 (3)
N1A—S1A—C1A106.36 (12)C14A—C15A—H15A115.4
O2B—S1B—O1B119.17 (12)C16A—C15A—H15A115.4
O2B—S1B—N1B109.69 (12)C2B—C1B—C6B120.6 (3)
O1B—S1B—N1B105.01 (12)C2B—C1B—S1B120.0 (3)
O2B—S1B—C1B107.17 (13)C6B—C1B—S1B119.3 (3)
O1B—S1B—C1B109.08 (13)C4A—C5A—C6A120.2 (3)
N1B—S1B—C1B106.03 (13)C4A—C5A—H5A119.9
C7A—N1A—S1A125.13 (17)C6A—C5A—H5A119.9
C7A—N1A—H1A116 (3)O4B—C19B—C18B124.5 (3)
S1A—N1A—H1A110 (3)O4B—C19B—C20B115.7 (3)
C19B—O4B—C22B116.9 (2)C18B—C19B—C20B119.7 (2)
C8B—C7B—C12B118.7 (2)C7A—C12A—C11A120.8 (3)
C8B—C7B—N1B117.6 (2)C7A—C12A—H12A119.6
C12B—C7B—N1B123.7 (2)C11A—C12A—H12A119.6
C17B—C16B—C21B117.1 (2)C9A—C8A—C7A120.6 (3)
C17B—C16B—C15B118.8 (2)C9A—C8A—H8A119.7
C21B—C16B—C15B124.0 (2)C7A—C8A—H8A119.7
C18B—C17B—C16B122.3 (2)C18A—C17A—C16A122.8 (3)
C18B—C17B—H17B118.9C18A—C17A—H17A118.6
C16B—C17B—H17B118.9C16A—C17A—H17A118.6
C7B—N1B—S1B126.34 (18)C19A—C18A—C17A119.2 (3)
C7B—N1B—H1B117 (3)C19A—C18A—H18A120.4
S1B—N1B—H1B112 (3)C17A—C18A—H18A120.4
C12B—C11B—C10B121.9 (2)C20A—C19A—C18A119.6 (3)
C12B—C11B—H11B119C20A—C19A—O4A115.6 (3)
C10B—C11B—H11B119C18A—C19A—O4A124.8 (3)
C12A—C7A—C8A117.9 (3)C1A—C2A—C3A119.7 (3)
C12A—C7A—N1A123.8 (2)C1A—C2A—H2A120.1
C8A—C7A—N1A118.1 (2)C3A—C2A—H2A120.1
C20B—C21B—C16B121.3 (2)C15A—C14A—C13A122.9 (3)
C20B—C21B—H21B119.3C15A—C14A—H14A118.5
C16B—C21B—H21B119.3C13A—C14A—H14A118.5
C11B—C12B—C7B120.0 (2)O4B—C22B—H22A109.5
C11B—C12B—H12B120O4B—C22B—H22B109.5
C7B—C12B—H12B120H22A—C22B—H22B109.5
C14B—C15B—C16B129.6 (2)O4B—C22B—H22C109.5
C14B—C15B—H15B115.2H22A—C22B—H22C109.5
C16B—C15B—H15B115.2H22B—C22B—H22C109.5
C17B—C18B—C19B119.4 (2)C21B—C20B—C19B120.2 (2)
C17B—C18B—H18B120.3C21B—C20B—H20B119.9
C19B—C18B—H18B120.3C19B—C20B—H20B119.9
C9B—C8B—C7B121.0 (2)C3A—C4A—C5A120.1 (3)
C9B—C8B—H8B119.5C3A—C4A—H4A120
C7B—C8B—H8B119.5C5A—C4A—H4A120
O3B—C13B—C14B120.4 (2)C5B—C4B—C3B122.0 (5)
O3B—C13B—C10B120.0 (2)C5B—C4B—H4B119
C14B—C13B—C10B119.7 (2)C3B—C4B—H4B119
C8B—C9B—C10B121.2 (2)C4A—C3A—C2A120.4 (3)
C8B—C9B—H9B119.4C4A—C3A—H3A119.8
C10B—C9B—H9B119.4C2A—C3A—H3A119.8
C2A—C1A—C6A120.3 (3)C8A—C9A—C10A122.3 (3)
C2A—C1A—S1A119.9 (2)C8A—C9A—H9A118.9
C6A—C1A—S1A119.8 (2)C10A—C9A—H9A118.9
C11B—C10B—C9B117.1 (2)C21A—C20A—C19A120.3 (3)
C11B—C10B—C13B123.7 (2)C21A—C20A—H20A119.9
C9B—C10B—C13B119.2 (2)C19A—C20A—H20A119.9
C19A—O4A—C22A118.1 (3)C1B—C6B—C5B120.5 (4)
C15B—C14B—C13B121.2 (2)C1B—C6B—H6B119.7
C15B—C14B—H14B119.4C5B—C6B—H6B119.7
C13B—C14B—H14B119.4C4B—C5B—C6B119.0 (4)
O3A—C13A—C14A120.3 (3)C4B—C5B—H5B120.5
O3A—C13A—C10A119.9 (3)C6B—C5B—H5B120.5
C14A—C13A—C10A119.7 (2)C4B—C3B—C2B118.9 (4)
C11A—C10A—C9A116.1 (3)C4B—C3B—H3B120.6
C11A—C10A—C13A123.9 (3)C2B—C3B—H3B120.6
C9A—C10A—C13A120.0 (3)C1B—C2B—C3B119.0 (4)
C17A—C16A—C21A116.1 (3)C1B—C2B—H2B120.5
C17A—C16A—C15A120.7 (3)C3B—C2B—H2B120.5
C21A—C16A—C15A123.2 (3)O4A—C22A—H22D109.5
C1A—C6A—C5A119.2 (3)O4A—C22A—H22E109.5
C1A—C6A—H6A120.4H22D—C22A—H22E109.5
C5A—C6A—H6A120.4O4A—C22A—H22F109.5
C10A—C11A—C12A122.3 (3)H22D—C22A—H22F109.5
C10A—C11A—H11A118.8H22E—C22A—H22F109.5
O1A—S1A—N1A—C7A179.4 (2)C17A—C16A—C15A—C14A179.6 (3)
O2A—S1A—N1A—C7A51.5 (2)C21A—C16A—C15A—C14A0.7 (5)
C1A—S1A—N1A—C7A64.6 (2)O2B—S1B—C1B—C2B161.1 (3)
C21B—C16B—C17B—C18B0.9 (4)O1B—S1B—C1B—C2B68.6 (3)
C15B—C16B—C17B—C18B178.3 (2)N1B—S1B—C1B—C2B44.0 (3)
C8B—C7B—N1B—S1B162.9 (2)O2B—S1B—C1B—C6B22.3 (3)
C12B—C7B—N1B—S1B18.1 (4)O1B—S1B—C1B—C6B108.0 (2)
O2B—S1B—N1B—C7B51.6 (3)N1B—S1B—C1B—C6B139.4 (2)
O1B—S1B—N1B—C7B179.2 (2)C1A—C6A—C5A—C4A1.1 (5)
C1B—S1B—N1B—C7B63.8 (3)C22B—O4B—C19B—C18B7.7 (4)
S1A—N1A—C7A—C12A33.5 (4)C22B—O4B—C19B—C20B170.9 (3)
S1A—N1A—C7A—C8A150.6 (2)C17B—C18B—C19B—O4B179.0 (3)
C17B—C16B—C21B—C20B0.7 (4)C17B—C18B—C19B—C20B0.4 (4)
C15B—C16B—C21B—C20B177.9 (3)C8A—C7A—C12A—C11A0.1 (5)
C10B—C11B—C12B—C7B1.5 (5)N1A—C7A—C12A—C11A175.9 (3)
C8B—C7B—C12B—C11B3.6 (5)C10A—C11A—C12A—C7A0.9 (5)
N1B—C7B—C12B—C11B175.4 (3)C12A—C7A—C8A—C9A0.8 (5)
C17B—C16B—C15B—C14B175.0 (3)N1A—C7A—C8A—C9A175.3 (3)
C21B—C16B—C15B—C14B7.9 (4)C21A—C16A—C17A—C18A0.7 (5)
C16B—C17B—C18B—C19B0.4 (4)C15A—C16A—C17A—C18A179.1 (3)
C12B—C7B—C8B—C9B2.7 (4)C16A—C17A—C18A—C19A0.7 (5)
N1B—C7B—C8B—C9B176.4 (2)C17A—C18A—C19A—C20A0.2 (5)
C7B—C8B—C9B—C10B0.4 (4)C17A—C18A—C19A—O4A179.7 (3)
O1A—S1A—C1A—C2A51.2 (3)C22A—O4A—C19A—C20A173.2 (3)
O2A—S1A—C1A—C2A177.8 (2)C22A—O4A—C19A—C18A6.9 (5)
N1A—S1A—C1A—C2A61.0 (3)C6A—C1A—C2A—C3A0.9 (5)
O1A—S1A—C1A—C6A125.9 (2)S1A—C1A—C2A—C3A178.1 (3)
O2A—S1A—C1A—C6A5.0 (2)C16A—C15A—C14A—C13A179.4 (3)
N1A—S1A—C1A—C6A121.8 (2)O3A—C13A—C14A—C15A8.1 (5)
C12B—C11B—C10B—C9B1.5 (4)C10A—C13A—C14A—C15A170.6 (3)
C12B—C11B—C10B—C13B178.6 (3)C16B—C21B—C20B—C19B0.1 (4)
C8B—C9B—C10B—C11B2.5 (4)O4B—C19B—C20B—C21B179.4 (3)
C8B—C9B—C10B—C13B177.6 (2)C18B—C19B—C20B—C21B0.7 (4)
O3B—C13B—C10B—C11B171.6 (2)C6A—C5A—C4A—C3A1.7 (5)
C14B—C13B—C10B—C11B9.8 (4)C5A—C4A—C3A—C2A0.9 (6)
O3B—C13B—C10B—C9B8.3 (3)C1A—C2A—C3A—C4A0.4 (6)
C14B—C13B—C10B—C9B170.3 (2)C7A—C8A—C9A—C10A0.7 (5)
C16B—C15B—C14B—C13B179.5 (2)C11A—C10A—C9A—C8A0.2 (5)
O3B—C13B—C14B—C15B3.1 (4)C13A—C10A—C9A—C8A177.4 (3)
C10B—C13B—C14B—C15B175.5 (2)C16A—C21A—C20A—C19A0.4 (6)
O3A—C13A—C10A—C11A177.0 (3)C18A—C19A—C20A—C21A0.3 (5)
C14A—C13A—C10A—C11A4.3 (4)O4A—C19A—C20A—C21A179.7 (3)
O3A—C13A—C10A—C9A5.6 (5)C2B—C1B—C6B—C5B0.5 (5)
C14A—C13A—C10A—C9A173.1 (3)S1B—C1B—C6B—C5B176.1 (3)
C2A—C1A—C6A—C5A0.2 (4)C3B—C4B—C5B—C6B1.6 (7)
S1A—C1A—C6A—C5A177.4 (2)C1B—C6B—C5B—C4B1.9 (6)
C9A—C10A—C11A—C12A1.0 (5)C5B—C4B—C3B—C2B0.2 (8)
C13A—C10A—C11A—C12A176.5 (3)C6B—C1B—C2B—C3B1.3 (6)
C17A—C16A—C21A—C20A0.1 (5)S1B—C1B—C2B—C3B177.9 (3)
C15A—C16A—C21A—C20A179.6 (3)C4B—C3B—C2B—C1B1.6 (7)
Hydrogen-bond geometry (Å, º) top
CgA is the centroid calculated through the ring A C atoms of molecule A.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Bi0.81 (5)2.16 (5)2.950 (3)166 (5)
N1B—H1B···O3Aii0.81 (5)2.11 (5)2.892 (3)163 (5)
C9A—H9A···O1Bii0.932.433.320 (4)160
C9B—H9B···O1Ai0.932.493.366 (3)157
C22B—H22A···O2Biii0.962.403.317 (4)160
C22A—H22D···CgAiv0.963.283.580 (4)101
C22A—H22E···CgAiv0.963.333.580 (4)97
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x, y+2, z+1.
(II) N-{4-[(E)-3-(4-Ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide top
Crystal data top
C23H21NO4SF(000) = 856
Mr = 407.47Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 4266 reflections
a = 8.4506 (2) Åθ = 2.9–26.4°
b = 20.1587 (6) ŵ = 0.18 mm1
c = 14.2120 (3) ÅT = 298 K
β = 119.098 (2)°Prism, yellow
V = 2115.49 (9) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
3072 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 9 pixels mm-1θmax = 26.4°, θmin = 3.2°
CCD scansh = 1010
7397 measured reflectionsk = 2325
4185 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0875P)2 + 0.0704P]
where P = (Fo2 + 2Fc2)/3
4185 reflections(Δ/σ)max < 0.001
265 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C23H21NO4SV = 2115.49 (9) Å3
Mr = 407.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4506 (2) ŵ = 0.18 mm1
b = 20.1587 (6) ÅT = 298 K
c = 14.2120 (3) Å0.25 × 0.20 × 0.15 mm
β = 119.098 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3072 reflections with I > 2σ(I)
7397 measured reflectionsRint = 0.036
4185 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.17 e Å3
4185 reflectionsΔρmin = 0.27 e Å3
265 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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) top
xyzUiso*/Ueq
S10.65679 (6)0.11848 (2)0.42888 (3)0.05750 (19)
N10.76455 (19)0.16732 (8)0.53375 (12)0.0606 (4)
O10.69037 (17)0.14641 (6)0.34799 (10)0.0709 (4)
O20.70805 (17)0.05154 (6)0.46160 (10)0.0678 (3)
O40.74263 (19)0.16891 (7)1.27909 (10)0.0753 (4)
C10.4242 (2)0.12732 (8)0.38628 (13)0.0546 (4)
C70.7578 (2)0.15805 (8)0.63097 (14)0.0565 (4)
C60.3341 (2)0.07890 (9)0.41042 (16)0.0677 (5)
H60.3950.04140.44910.081*
C130.7446 (3)0.13877 (10)0.92840 (15)0.0660 (5)
C210.7434 (3)0.05952 (10)1.07881 (15)0.0723 (5)
H210.75250.06381.01650.087*
C100.7513 (2)0.14366 (9)0.82493 (14)0.0601 (4)
C190.7346 (2)0.11021 (9)1.22857 (14)0.0640 (5)
O30.7338 (2)0.18963 (7)0.97259 (11)0.0833 (4)
C220.7544 (3)0.16605 (10)1.38310 (15)0.0747 (5)
H22A0.64520.14661.37740.09*
H22B0.85690.1391.43150.09*
C150.7296 (3)0.06480 (10)1.06029 (15)0.0700 (5)
H150.71490.10351.09080.084*
C90.7312 (3)0.20515 (9)0.77736 (16)0.0722 (5)
H90.71660.24240.81090.087*
C180.7174 (3)0.04923 (9)1.26476 (15)0.0693 (5)
H180.70810.04551.32710.083*
C170.7140 (3)0.00713 (10)1.20731 (15)0.0716 (5)
H170.70170.04841.23220.086*
C80.7323 (3)0.21237 (9)0.68120 (15)0.0684 (5)
H80.71570.25410.650.082*
C200.7449 (3)0.11520 (10)1.13412 (15)0.0722 (5)
H200.7530.15681.10840.087*
C160.7284 (2)0.00392 (9)1.11405 (14)0.0652 (5)
C20.3369 (3)0.18415 (9)0.33206 (16)0.0700 (5)
H20.40020.21730.31890.084*
C120.7835 (3)0.09649 (10)0.67957 (16)0.0743 (5)
H120.80520.05960.64820.089*
C50.1508 (3)0.08715 (10)0.37601 (17)0.0754 (5)
H50.08820.0550.39180.09*
C140.7485 (3)0.07314 (10)0.97391 (16)0.0720 (5)
H140.76490.0360.94080.086*
C40.0624 (3)0.14239 (10)0.31898 (16)0.0741 (5)
H40.0610.14710.29440.089*
C110.7769 (3)0.08960 (10)0.77449 (15)0.0728 (5)
H110.79010.04770.80480.087*
C30.1549 (3)0.19133 (10)0.29755 (17)0.0783 (5)
H30.09410.22910.25980.094*
C230.7774 (4)0.23565 (12)1.42532 (19)0.0988 (7)
H23A0.78560.23511.49510.148*
H23B0.88610.25441.43090.148*
H23C0.67520.26191.3770.148*
H10.763 (3)0.2108 (14)0.516 (2)0.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0687 (3)0.0501 (3)0.0675 (3)0.00035 (18)0.0439 (2)0.00150 (18)
N10.0657 (8)0.0533 (8)0.0708 (9)0.0046 (6)0.0394 (7)0.0013 (7)
O10.0923 (9)0.0643 (8)0.0829 (8)0.0019 (6)0.0637 (8)0.0005 (6)
O20.0830 (8)0.0490 (7)0.0819 (8)0.0063 (5)0.0485 (7)0.0001 (6)
O40.1070 (10)0.0633 (8)0.0669 (7)0.0010 (7)0.0510 (7)0.0033 (6)
C10.0645 (9)0.0506 (9)0.0551 (9)0.0017 (7)0.0340 (8)0.0008 (7)
C70.0548 (8)0.0524 (10)0.0644 (10)0.0059 (7)0.0306 (8)0.0057 (8)
C60.0702 (11)0.0548 (10)0.0800 (12)0.0034 (8)0.0382 (9)0.0082 (9)
C130.0730 (11)0.0624 (11)0.0661 (10)0.0069 (8)0.0367 (9)0.0077 (9)
C210.0931 (13)0.0719 (13)0.0617 (10)0.0031 (10)0.0453 (10)0.0083 (9)
C100.0624 (9)0.0547 (10)0.0650 (10)0.0055 (8)0.0324 (8)0.0062 (8)
C190.0735 (11)0.0605 (11)0.0616 (10)0.0038 (8)0.0356 (9)0.0066 (8)
O30.1218 (12)0.0609 (8)0.0834 (9)0.0081 (7)0.0624 (9)0.0125 (7)
C220.0906 (13)0.0795 (13)0.0630 (11)0.0084 (10)0.0443 (10)0.0071 (10)
C150.0829 (12)0.0629 (11)0.0660 (11)0.0072 (9)0.0378 (10)0.0082 (9)
C90.0961 (14)0.0548 (11)0.0798 (12)0.0048 (9)0.0539 (11)0.0092 (9)
C180.0853 (12)0.0675 (12)0.0656 (11)0.0111 (9)0.0449 (10)0.0133 (9)
C170.0899 (13)0.0631 (12)0.0714 (11)0.0095 (9)0.0466 (10)0.0148 (9)
C80.0866 (12)0.0506 (10)0.0780 (12)0.0048 (8)0.0480 (10)0.0030 (9)
C200.0974 (14)0.0605 (11)0.0687 (11)0.0015 (9)0.0483 (11)0.0093 (9)
C160.0715 (11)0.0628 (11)0.0634 (10)0.0081 (8)0.0345 (9)0.0081 (9)
C20.0730 (11)0.0614 (11)0.0834 (12)0.0005 (9)0.0442 (10)0.0143 (9)
C120.1028 (14)0.0555 (11)0.0735 (12)0.0111 (10)0.0498 (11)0.0002 (9)
C50.0743 (12)0.0674 (13)0.0917 (14)0.0129 (9)0.0462 (11)0.0025 (10)
C140.0874 (13)0.0615 (11)0.0742 (12)0.0045 (9)0.0448 (11)0.0070 (9)
C40.0628 (10)0.0768 (13)0.0832 (12)0.0003 (9)0.0360 (10)0.0007 (11)
C110.0958 (14)0.0563 (11)0.0715 (11)0.0035 (9)0.0447 (11)0.0015 (9)
C30.0718 (12)0.0738 (13)0.0887 (13)0.0083 (9)0.0385 (10)0.0169 (11)
C230.133 (2)0.0928 (17)0.0818 (14)0.0041 (14)0.0610 (15)0.0078 (12)
Geometric parameters (Å, º) top
S1—O21.4245 (13)C22—H22B0.97
S1—O11.4269 (12)C15—C141.324 (3)
S1—N11.6432 (15)C15—C161.448 (2)
S1—C11.7621 (17)C15—H150.93
N1—C71.423 (2)C9—C81.379 (3)
N1—H10.91 (3)C9—H90.93
O4—C191.369 (2)C18—C171.391 (3)
O4—C221.434 (2)C18—H180.93
C1—C21.378 (2)C17—C161.390 (2)
C1—C61.380 (2)C17—H170.93
C7—C81.380 (2)C8—H80.93
C7—C121.385 (2)C20—H200.93
C6—C51.388 (2)C2—C31.376 (3)
C6—H60.93C2—H20.93
C13—O31.228 (2)C12—C111.384 (3)
C13—C141.466 (3)C12—H120.93
C13—C101.502 (2)C5—C41.366 (3)
C21—C201.367 (3)C5—H50.93
C21—C161.402 (2)C14—H140.93
C21—H210.93C4—C31.381 (3)
C10—C111.378 (2)C4—H40.93
C10—C91.382 (3)C11—H110.93
C19—C181.367 (3)C3—H30.93
C19—C201.390 (2)C23—H23A0.96
C22—C231.501 (3)C23—H23B0.96
C22—H22A0.97C23—H23C0.96
O2—S1—O1119.26 (7)C19—C18—C17119.28 (16)
O2—S1—N1108.97 (8)C19—C18—H18120.4
O1—S1—N1104.76 (8)C17—C18—H18120.4
O2—S1—C1108.62 (7)C16—C17—C18122.35 (17)
O1—S1—C1108.00 (8)C16—C17—H17118.8
N1—S1—C1106.53 (7)C18—C17—H17118.8
C7—N1—S1122.41 (11)C9—C8—C7120.45 (17)
C7—N1—H1113.0 (16)C9—C8—H8119.8
S1—N1—H1113.6 (17)C7—C8—H8119.8
C19—O4—C22117.85 (14)C21—C20—C19120.54 (17)
C2—C1—C6121.14 (16)C21—C20—H20119.7
C2—C1—S1118.74 (12)C19—C20—H20119.7
C6—C1—S1120.09 (13)C17—C16—C21116.63 (17)
C8—C7—C12118.61 (16)C17—C16—C15119.34 (17)
C8—C7—N1119.22 (15)C21—C16—C15124.02 (17)
C12—C7—N1122.11 (15)C3—C2—C1119.25 (17)
C1—C6—C5118.90 (17)C3—C2—H2120.4
C1—C6—H6120.5C1—C2—H2120.4
C5—C6—H6120.5C11—C12—C7120.35 (17)
O3—C13—C14121.27 (17)C11—C12—H12119.8
O3—C13—C10119.55 (17)C7—C12—H12119.8
C14—C13—C10119.18 (16)C4—C5—C6120.08 (17)
C20—C21—C16121.40 (17)C4—C5—H5120
C20—C21—H21119.3C6—C5—H5120
C16—C21—H21119.3C15—C14—C13122.46 (18)
C11—C10—C9117.89 (16)C15—C14—H14118.8
C11—C10—C13123.20 (17)C13—C14—H14118.8
C9—C10—C13118.90 (16)C5—C4—C3120.54 (18)
C18—C19—O4124.55 (16)C5—C4—H4119.7
C18—C19—C20119.76 (18)C3—C4—H4119.7
O4—C19—C20115.69 (16)C10—C11—C12121.23 (18)
O4—C22—C23107.77 (16)C10—C11—H11119.4
O4—C22—H22A110.2C12—C11—H11119.4
C23—C22—H22A110.2C2—C3—C4120.03 (18)
O4—C22—H22B110.2C2—C3—H3120
C23—C22—H22B110.2C4—C3—H3120
H22A—C22—H22B108.5C22—C23—H23A109.5
C14—C15—C16129.19 (18)C22—C23—H23B109.5
C14—C15—H15115.4H23A—C23—H23B109.5
C16—C15—H15115.4C22—C23—H23C109.5
C8—C9—C10121.40 (17)H23A—C23—H23C109.5
C8—C9—H9119.3H23B—C23—H23C109.5
C10—C9—H9119.3
O2—S1—N1—C754.26 (15)C12—C7—C8—C90.5 (3)
O1—S1—N1—C7177.05 (13)N1—C7—C8—C9177.83 (16)
C1—S1—N1—C762.76 (15)C16—C21—C20—C191.1 (3)
O2—S1—C1—C2167.78 (14)C18—C19—C20—C211.9 (3)
O1—S1—C1—C237.10 (16)O4—C19—C20—C21178.15 (18)
N1—S1—C1—C274.98 (15)C18—C17—C16—C211.1 (3)
O2—S1—C1—C614.36 (17)C18—C17—C16—C15178.05 (18)
O1—S1—C1—C6145.04 (14)C20—C21—C16—C170.4 (3)
N1—S1—C1—C6102.89 (15)C20—C21—C16—C15178.72 (19)
S1—N1—C7—C8135.53 (15)C14—C15—C16—C17177.28 (19)
S1—N1—C7—C1247.2 (2)C14—C15—C16—C211.8 (3)
C2—C1—C6—C52.1 (3)C6—C1—C2—C32.7 (3)
S1—C1—C6—C5179.91 (14)S1—C1—C2—C3179.41 (15)
O3—C13—C10—C11175.02 (19)C8—C7—C12—C112.3 (3)
C14—C13—C10—C115.8 (3)N1—C7—C12—C11179.61 (17)
O3—C13—C10—C94.9 (3)C1—C6—C5—C40.2 (3)
C14—C13—C10—C9174.23 (18)C16—C15—C14—C13179.29 (18)
C22—O4—C19—C187.4 (3)O3—C13—C14—C154.3 (3)
C22—O4—C19—C20172.68 (17)C10—C13—C14—C15174.90 (17)
C19—O4—C22—C23175.26 (17)C6—C5—C4—C31.8 (3)
C11—C10—C9—C81.5 (3)C9—C10—C11—C120.4 (3)
C13—C10—C9—C8178.55 (16)C13—C10—C11—C12179.56 (17)
O4—C19—C18—C17178.87 (18)C7—C12—C11—C102.3 (3)
C20—C19—C18—C171.2 (3)C1—C2—C3—C41.1 (3)
C19—C18—C17—C160.3 (3)C5—C4—C3—C21.2 (3)
C10—C9—C8—C71.5 (3)
Hydrogen-bond geometry (Å, º) top
CgA is the centroid calculated through the ring A C atoms.
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.91 (3)2.08 (3)2.987 (2)175 (3)
C9—H9···O1ii0.932.343.228 (2)160
C23—H23A···CgAiii0.963.043.816 (3)138
C2—H2···O4iv0.932.653.269 (2)125
C3—H3···O4iv0.932.683.285 (2)124
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2; (iii) x+1, y, z+2; (iv) x+1, y+1/2, z+3/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC22H19NO4SC23H21NO4S
Mr393.44407.47
Crystal system, space groupTriclinic, P1Monoclinic, P21/c
Temperature (K)298298
a, b, c (Å)11.8650 (3), 12.2420 (3), 14.7287 (3)8.4506 (2), 20.1587 (6), 14.2120 (3)
α, β, γ (°)68.075 (1), 81.665 (1), 80.437 (1)90, 119.098 (2), 90
V3)1948.99 (8)2115.49 (9)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.190.18
Crystal size (mm)0.28 × 0.15 × 0.080.25 × 0.20 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
22723, 8378, 5268 7397, 4185, 3072
Rint0.0390.036
(sin θ/λ)max1)0.6370.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.152, 1.02 0.049, 0.143, 1.05
No. of reflections83784185
No. of parameters512265
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.270.17, 0.27

Computer programs: COLLECT (Nonius, 2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) for (I) top
CgA is the centroid calculated through the ring A C atoms of molecule A.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Bi0.81 (5)2.16 (5)2.950 (3)166 (5)
N1B—H1B···O3Aii0.81 (5)2.11 (5)2.892 (3)163 (5)
C9A—H9A···O1Bii0.932.433.320 (4)160
C9B—H9B···O1Ai0.932.493.366 (3)157
C22B—H22A···O2Biii0.962.403.317 (4)160
C22A—H22D···CgAiv0.963.283.580 (4)101
C22A—H22E···CgAiv0.963.333.580 (4)97
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
CgA is the centroid calculated through the ring A C atoms.
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.91 (3)2.08 (3)2.987 (2)175 (3)
C9—H9···O1ii0.932.343.228 (2)160
C23—H23A···CgAiii0.963.043.816 (3)138
C2—H2···O4iv0.932.653.269 (2)125
C3—H3···O4iv0.932.683.285 (2)124
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2; (iii) x+1, y, z+2; (iv) x+1, y+1/2, z+3/2.
 

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