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The title compound, C21H21NO7S3, consists of an SO2ON(SO2)2 central fragment and three terminal 4-methyl­phenyl groups each attached at a sulfonyl S atom. The most obvious characteristic is the presence of two nearly face-to-face benzene rings, with their centroids separated by a rather short distance [3.7808 (18) Å], but with a rather slanted relative orientation [dihedral angle = 20.63 (13)°] so as to preclude a strong intra­molecular π–π inter­action. The third benzene ring is nearly perpendicular to the other two [dihedral angles = 71.62 (14) and 70.4 (13)°]. The packing of the structure is directed by two C—H...O hydrogen bonds involving aromatic H atoms (methyl H atoms are strictly non-inter­acting), which define chains running in the [100] direction. These one-dimensional chains evolve parallel to each other and exhibit no significant lateral inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112039182/dt3015sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112039182/dt3015Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112039182/dt3015Isup3.cml
Supplementary material

CCDC reference: 906588

Comment top

The hydroxylamine (–NH2OH) group has proven to be, through H-atom substitution, the basis of a number of different compounds having varied formulation and interesting structures. One of these groups, with the general formula(RSO2)2NOSO2R is attracting our current interest. Many members of this family (viz. R = OH, F, Me, CF3, Ph, PhCH3 and PhBr; Birchall & Glidewell, 1977; Brink & Mattes, 1985; Ruff & Merritt, 1968; Tomita, 2002) and even some R,R' mixed combinations (viz. R = Ph; R' = PhCH3, PhNO2; Farrar, 1960; Wowski & Scheittele, 1965) have been reported. In addition, their formation mechanisms starting from radicals (Birchall & Glidewell, 1978) and their characterization using a diversity of spectroscopic techniques (Glidewell & Davie, 1981) have been studied. [Do you want to put specific references with specific substituents?]

In this context, it is surprising that only a couple of structures of this family have been reported so far, namely those with R = Ph, (II) (Scholz et al., 1989), and R = Me, (III) (Brink & Mattes, 1986). We present herein the structural study of a third member of the family, that with R = Ph-4-CH3 (p-tosyl), namely bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate, (I), and the results are compared with those of the related structures (II) and (III).

The molecule of (I) (Fig. 1) is built around the S2—N—OS nucleus and the pyramidal geometry around the N atom seems to be sensitive to the characteristics of the R groups attached to the S atoms, as a comparison within the (I)–(III) family highlights; Table 1 presents some relevant distances and angles in the neighbourhood of atom N1 in all three structures and it is apparent from inspection that the distances are basically stable, while the angles, in particular the S—N—S angles, are not.

The most obvious characteristic in the molecular geometry of (I) is the presence of two nearly face-to-face benzene rings [denoted Ph1 (atoms C11/C21/C31/C41/C51/C61) and Ph2 (C12/C22/C32/C42/C52/C62)], the third ring, Ph3 (atoms C13/C23/C33/C43/C53/C63), being nearly perpendicular to Ph1 and Ph2, subtending dihedral angles of 71.62 (14) and 70.4 (13)°, respectively. The face-to-face relative positioning of Ph1 and Ph2 is not the result of steric hindrance (there are enough rotational degrees of freedom as to avoid any Ph···Ph bumping), but what this positioning suggests is some kind of ππ interaction, albeit weak; the centroids are at a rather short distance of 3.7808 (18) Å, but they present a rather slanted relative orientation for a strong intramolecular ππ bond to build up. A similar disposition (discussed below) is found in the closely related structure (II) (R = Ph instead of R = Ph-4-CH3). Fig. 2 presents a schematic overlap of both structures which allows similarities (mainly in the central nuclei) and differences (rotated terminal benzene arms) between the structures to be assessed.

The packing of (I) is directed by a couple of C—H···O hydrogen bonds involving aromatic H atoms (Table 2), methyl H atoms being strictly non-interacting. These hydrogen bonds define chains running in the [100] direction (Fig. 3a), parallel to each other and display no significant lateral interactions. This fact can be appreciated in Fig. 3(b), where chains are seen in projection and from which it is clear that aromatic rings are not located in favourable positions for interchain ππ bonding, the most significant contact of this sort being that presented in Table 3 for compound (I) (2nd entry).

This lack of significant intermolecular interactions introduces some differences in comparison with (II), which displays a clear well established intermolecular ππ bond around an inversion centre [Table 3, compound (II), 2nd entry], defining a close dimeric entity. In addition to the more diffuse (and difficult to assess) packing forces, this latter interaction might be partially responsible for the more open disposition of the benzene rings [Ph1···Ph2 internal angle = 32.67 (16)° in (II) versus 20.63 (13)° in (I)], leading to weaker intramolecular interactions [Table 3, compound (II), 1st entry]. There are no further intermolecular interactions in (II), apart from the dimeric contact described. This different affinity for ππ bonding in otherwise similar molecular structures might well be due to the disrupting presence of the bulky methyl groups in (I).

Comparison with the much simpler structure (III) is perhaps less significant in that the substituent groups are very different [R = Me in (III) versus R = Ph in (I)], but it allows nonetheless for an interesting digression regarding hydrogen -bonding affinity of the usually `inert' methyl H atoms. In fact, the Ph-4-CH3 groups in (I) do not exhibit intra/interatomic interactions of any kind (this is an expected behaviour for this type of group for unpolarized H atoms [rewording OK?]). In contrast with this situation, the methyl groups in (III) are very active from a hydrogen-bonding point of view, probably due to their more acidic character derived from their direct binding to sulfur. As a result, packing is achieved in the form of very broad two-dimensional structures where (C—H)methyl···O hydrogen bonds are the only `gluing' agent.

As a final remark regarding packing efficiency, as measured by the `packing index' (pi) provided by the 2012 version of PLATON (Spek, 2009), viz. 65.9 for (I), 67.7 for (II) and 70.6 for (III), the most compact structure is (III), achieved through the usually inert (C—H)methyl donors. This is followed by (II), with only one significant intermolecular Cg···Cg interaction defining centrosymmetric dimers but no further relevant inter-dimeric contacts. Bottom ranked is (I) with a variety of presumably significant (C—H)ar···O and Cg···Cg interactions. This analysis confirms that packing efficiency should be thought of as a complex combination of factors (molecular geometry, steric effects etc), rather than the straightforward result of intermolecular interactions alone.

Related literature top

For related literature, see: Birchall & Glidewell (1977, 1978); Brink & Mattes (1985, 1986); Farrar (1960); Glidewell & Davie (1981); Ruff & Merritt (1968); Scholz et al. (1989); Spek (2009); Tomita (2002); Wowski & Scheittele (1965).

Experimental top

The title compound was obtained as a by-product during the synthesis of N-hydroxy-4-methylbenzenesulfonamide according to the procedure of Scholz et al. (1989). A few colorless prism-shaped crystals were obtained by evaporation from an acetonitrile solution.

Refinement top

H atoms attached to C atoms atoms were found in a difference map, were further idealized and were finally allowed to ride. Methyl groups were also free to rotate. For methyl H atoms, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C), and for aromatic H atoms, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 40% probability level.
[Figure 2] Fig. 2. A schematic superposition of (I) (full lines) and (II) (broken lines), where only the NS2O inner groups were included in a least-squares match. Note the almost perfect fit displayed by the nuclei and the (rotational) misfit in the pendant arms.
[Figure 3] Fig. 3. Packing views of (I) for (a) a projection down [010] showing a couple of isolated chains and the way in which they are formed, and (b) a projection down [100] showing chains (with different shading for clarity) coming upwards. Note the lack of relevant interchain interactions. [Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+2, -y+2, -z+2.]
Bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate top
Crystal data top
C21H21NO7S3F(000) = 1032
Mr = 495.57Dx = 1.424 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4103 reflections
a = 14.6523 (6) Åθ = 3.7–28.8°
b = 9.9342 (5) ŵ = 0.36 mm1
c = 16.0953 (6) ÅT = 295 K
β = 99.355 (4)°Prisms, colourless
V = 2311.65 (17) Å30.20 × 0.15 × 0.15 mm
Z = 4
Data collection top
Oxford Diffraction Gemini CCD S Ultra
diffractometer
5389 independent reflections
Radiation source: fine-focus sealed tube2771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ω scans, thick slicesθmax = 28.8°, θmin = 3.7°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
h = 1919
Tmin = 0.945, Tmax = 0.952k = 1313
15723 measured reflectionsl = 2021
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0356P)2 + 0.486P]
where P = (Fo2 + 2Fc2)/3
5389 reflections(Δ/σ)max = 0.001
292 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C21H21NO7S3V = 2311.65 (17) Å3
Mr = 495.57Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.6523 (6) ŵ = 0.36 mm1
b = 9.9342 (5) ÅT = 295 K
c = 16.0953 (6) Å0.20 × 0.15 × 0.15 mm
β = 99.355 (4)°
Data collection top
Oxford Diffraction Gemini CCD S Ultra
diffractometer
5389 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
2771 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.952Rint = 0.068
15723 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.99Δρmax = 0.28 e Å3
5389 reflectionsΔρmin = 0.20 e Å3
292 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.64217 (5)1.05279 (8)0.84217 (4)0.0590 (2)
S20.70071 (5)1.03700 (7)1.03406 (4)0.05370 (19)
S30.88243 (5)1.17019 (8)0.92356 (4)0.0583 (2)
O110.68307 (14)1.1219 (2)0.78017 (11)0.0757 (6)
O210.55578 (12)1.0922 (2)0.86219 (12)0.0747 (6)
O120.61333 (12)1.09443 (18)1.04105 (11)0.0644 (5)
O220.78335 (12)1.08180 (19)1.08539 (11)0.0666 (5)
O130.83000 (14)1.29006 (19)0.91856 (12)0.0741 (6)
O230.95277 (12)1.1446 (2)0.99318 (11)0.0763 (6)
N10.71880 (13)1.0808 (2)0.93407 (12)0.0516 (5)
C110.64351 (18)0.8815 (3)0.82238 (15)0.0535 (7)
C210.5743 (2)0.8003 (3)0.84448 (16)0.0642 (8)
H210.52660.83710.86890.077*
C310.5776 (2)0.6633 (4)0.82941 (18)0.0760 (9)
H310.53140.60790.84370.091*
C410.6481 (3)0.6076 (4)0.79354 (19)0.0793 (10)
C510.7144 (2)0.6914 (4)0.77068 (19)0.0790 (10)
H510.76110.65480.74490.095*
C610.7136 (2)0.8264 (3)0.78470 (16)0.0692 (8)
H610.75960.88110.76920.083*
C710.6501 (3)0.4576 (4)0.7794 (2)0.1166 (14)
H71A0.64540.43960.72020.175*
H71B0.59910.41630.80030.175*
H71C0.70720.42140.80860.175*
C120.69481 (17)0.8623 (3)1.03894 (14)0.0481 (6)
C220.61244 (19)0.8027 (3)1.05039 (15)0.0580 (7)
H220.56050.85511.05340.070*
C320.6082 (2)0.6651 (3)1.05717 (16)0.0668 (8)
H320.55310.62551.06610.080*
C420.6830 (2)0.5841 (3)1.05120 (16)0.0646 (8)
C520.7645 (2)0.6458 (3)1.03959 (18)0.0725 (9)
H520.81590.59271.03540.087*
C620.77195 (18)0.7825 (3)1.03406 (17)0.0655 (8)
H620.82780.82181.02710.079*
C720.6760 (2)0.4331 (3)1.0568 (2)0.0937 (11)
H72A0.67060.40791.11340.141*
H72B0.73050.39271.04160.141*
H72C0.62250.40261.01910.141*
C130.92562 (17)1.1392 (3)0.83080 (15)0.0509 (6)
C230.88491 (19)1.1969 (3)0.75569 (17)0.0638 (8)
H230.83131.24790.75310.077*
C330.9245 (2)1.1781 (3)0.68498 (16)0.0684 (8)
H330.89781.21840.63470.082*
C431.0027 (2)1.1010 (3)0.68671 (17)0.0644 (8)
C531.04090 (19)1.0425 (3)0.76170 (17)0.0686 (8)
H531.09350.98940.76370.082*
C631.00350 (18)1.0603 (3)0.83377 (16)0.0608 (7)
H631.03031.01980.88390.073*
C731.0461 (2)1.0825 (4)0.60865 (18)0.1033 (13)
H73A1.07431.16540.59550.155*
H73B0.99941.05700.56240.155*
H73C1.09241.01330.61840.155*
O330.80876 (11)1.04082 (17)0.92177 (10)0.0543 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0591 (4)0.0663 (5)0.0511 (4)0.0075 (4)0.0073 (3)0.0033 (4)
S20.0558 (4)0.0581 (4)0.0492 (4)0.0018 (4)0.0144 (3)0.0024 (3)
S30.0619 (4)0.0613 (5)0.0542 (4)0.0092 (4)0.0168 (3)0.0041 (4)
O110.0903 (14)0.0822 (15)0.0552 (11)0.0033 (11)0.0140 (10)0.0149 (10)
O210.0580 (12)0.0880 (15)0.0770 (13)0.0228 (11)0.0074 (10)0.0018 (11)
O120.0630 (12)0.0654 (13)0.0703 (12)0.0135 (10)0.0276 (10)0.0025 (10)
O220.0672 (12)0.0775 (14)0.0534 (10)0.0118 (10)0.0052 (9)0.0075 (10)
O130.0844 (14)0.0528 (13)0.0927 (14)0.0022 (11)0.0371 (11)0.0049 (11)
O230.0689 (12)0.1063 (17)0.0517 (11)0.0163 (12)0.0038 (10)0.0085 (11)
N10.0451 (12)0.0591 (14)0.0530 (12)0.0032 (11)0.0149 (10)0.0018 (10)
C110.0534 (16)0.0668 (19)0.0392 (14)0.0062 (15)0.0040 (12)0.0057 (13)
C210.0567 (18)0.079 (2)0.0550 (16)0.0031 (16)0.0034 (13)0.0052 (16)
C310.088 (2)0.072 (2)0.0615 (19)0.020 (2)0.0054 (17)0.0009 (18)
C410.097 (3)0.076 (2)0.0561 (19)0.017 (2)0.0143 (18)0.0110 (18)
C510.080 (2)0.090 (3)0.065 (2)0.021 (2)0.0092 (17)0.0172 (19)
C610.069 (2)0.083 (2)0.0567 (17)0.0016 (18)0.0134 (14)0.0079 (17)
C710.156 (4)0.079 (3)0.100 (3)0.016 (3)0.024 (2)0.018 (2)
C120.0481 (16)0.0569 (17)0.0399 (13)0.0023 (13)0.0088 (11)0.0023 (12)
C220.0535 (17)0.060 (2)0.0619 (17)0.0070 (14)0.0129 (13)0.0023 (14)
C320.0641 (19)0.071 (2)0.0679 (19)0.0089 (17)0.0190 (15)0.0021 (17)
C420.082 (2)0.060 (2)0.0542 (17)0.0031 (17)0.0185 (15)0.0020 (14)
C520.072 (2)0.065 (2)0.087 (2)0.0227 (17)0.0287 (17)0.0115 (17)
C620.0497 (18)0.071 (2)0.078 (2)0.0124 (15)0.0179 (15)0.0100 (16)
C720.127 (3)0.064 (2)0.094 (2)0.005 (2)0.030 (2)0.0081 (19)
C130.0491 (15)0.0562 (17)0.0482 (14)0.0017 (13)0.0100 (12)0.0044 (13)
C230.0570 (17)0.072 (2)0.0650 (18)0.0173 (15)0.0167 (14)0.0163 (15)
C330.073 (2)0.084 (2)0.0482 (16)0.0168 (18)0.0082 (14)0.0168 (16)
C430.0658 (18)0.075 (2)0.0555 (17)0.0161 (16)0.0179 (14)0.0067 (15)
C530.0636 (18)0.077 (2)0.0684 (18)0.0247 (17)0.0207 (15)0.0139 (17)
C630.0524 (16)0.077 (2)0.0524 (15)0.0090 (15)0.0076 (13)0.0172 (15)
C730.113 (3)0.145 (4)0.0572 (19)0.051 (3)0.0297 (18)0.012 (2)
O330.0540 (10)0.0541 (11)0.0584 (10)0.0013 (9)0.0201 (8)0.0000 (9)
Geometric parameters (Å, º) top
S1—O211.4115 (19)C12—C621.393 (3)
S1—O111.4214 (19)C22—C321.373 (4)
S1—N11.728 (2)C22—H220.9300
S1—C111.732 (3)C32—C421.376 (4)
S2—O221.4218 (18)C32—H320.9300
S2—O121.4228 (17)C42—C521.382 (4)
S2—N11.729 (2)C42—C721.507 (4)
S2—C121.740 (3)C52—C621.367 (4)
S3—O131.412 (2)C52—H520.9300
S3—O231.4167 (19)C62—H620.9300
S3—O331.6756 (18)C72—H72A0.9600
S3—C131.741 (2)C72—H72B0.9600
N1—O331.421 (2)C72—H72C0.9600
C11—C211.387 (4)C13—C631.379 (3)
C11—C611.388 (4)C13—C231.383 (3)
C21—C311.385 (4)C23—C331.371 (4)
C21—H210.9300C23—H230.9300
C31—C411.379 (4)C33—C431.376 (4)
C31—H310.9300C33—H330.9300
C41—C511.375 (5)C43—C531.374 (4)
C41—C711.508 (5)C43—C731.509 (4)
C51—C611.360 (4)C53—C631.372 (3)
C51—H510.9300C53—H530.9300
C61—H610.9300C63—H630.9300
C71—H71A0.9600C73—H73A0.9600
C71—H71B0.9600C73—H73B0.9600
C71—H71C0.9600C73—H73C0.9600
C12—C221.383 (3)
O21—S1—O11121.48 (13)C62—C12—S2121.2 (2)
O21—S1—N1104.00 (11)C32—C22—C12119.2 (3)
O11—S1—N1103.52 (11)C32—C22—H22120.4
O21—S1—C11110.62 (13)C12—C22—H22120.4
O11—S1—C11109.07 (13)C22—C32—C42122.0 (3)
N1—S1—C11106.88 (11)C22—C32—H32119.0
O22—S2—O12121.39 (11)C42—C32—H32119.0
O22—S2—N1102.55 (10)C32—C42—C52117.8 (3)
O12—S2—N1104.41 (10)C32—C42—C72121.0 (3)
O22—S2—C12109.26 (12)C52—C42—C72121.2 (3)
O12—S2—C12110.14 (12)C62—C52—C42122.0 (3)
N1—S2—C12108.01 (11)C62—C52—H52119.0
O13—S3—O23121.02 (13)C42—C52—H52119.0
O13—S3—O33107.63 (10)C52—C62—C12119.2 (3)
O23—S3—O33105.06 (11)C52—C62—H62120.4
O13—S3—C13111.73 (12)C12—C62—H62120.4
O23—S3—C13109.12 (12)C42—C72—H72A109.5
O33—S3—C1399.95 (10)C42—C72—H72B109.5
O33—N1—S1108.91 (14)H72A—C72—H72B109.5
O33—N1—S2110.21 (14)C42—C72—H72C109.5
S1—N1—S2125.43 (12)H72A—C72—H72C109.5
C21—C11—C61120.5 (3)H72B—C72—H72C109.5
C21—C11—S1119.6 (2)C63—C13—C23120.2 (2)
C61—C11—S1119.9 (2)C63—C13—S3119.0 (2)
C31—C21—C11118.6 (3)C23—C13—S3120.8 (2)
C31—C21—H21120.7C33—C23—C13119.3 (2)
C11—C21—H21120.7C33—C23—H23120.4
C41—C31—C21121.2 (3)C13—C23—H23120.4
C41—C31—H31119.4C23—C33—C43121.5 (2)
C21—C31—H31119.4C23—C33—H33119.3
C51—C41—C31118.6 (3)C43—C33—H33119.3
C51—C41—C71121.7 (4)C53—C43—C33118.2 (3)
C31—C41—C71119.7 (4)C53—C43—C73120.9 (3)
C61—C51—C41121.9 (3)C33—C43—C73120.9 (3)
C61—C51—H51119.1C63—C53—C43121.8 (3)
C41—C51—H51119.1C63—C53—H53119.1
C51—C61—C11119.2 (3)C43—C53—H53119.1
C51—C61—H61120.4C53—C63—C13119.1 (2)
C11—C61—H61120.4C53—C63—H63120.5
C41—C71—H71A109.5C13—C63—H63120.5
C41—C71—H71B109.5C43—C73—H73A109.5
H71A—C71—H71B109.5C43—C73—H73B109.5
C41—C71—H71C109.5H73A—C73—H73B109.5
H71A—C71—H71C109.5C43—C73—H73C109.5
H71B—C71—H71C109.5H73A—C73—H73C109.5
C22—C12—C62119.8 (3)H73B—C73—H73C109.5
C22—C12—S2118.9 (2)N1—O33—S3113.13 (14)
Hydrogen-bond geometry (Å, º) top
Table 2. Hydrogen bond geometry for (I) (Å, °).
D—H···AD—HH···AD···AD—H···A
C22—H22···O21i0.932.403.205 (3)144
C63—H63···O23ii0.932.553.425 (3)158
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC21H21NO7S3
Mr495.57
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)14.6523 (6), 9.9342 (5), 16.0953 (6)
β (°) 99.355 (4)
V3)2311.65 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.20 × 0.15 × 0.15
Data collection
DiffractometerOxford Diffraction Gemini CCD S Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.945, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
15723, 5389, 2771
Rint0.068
(sin θ/λ)max1)0.679
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.102, 0.99
No. of reflections5389
No. of parameters292
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Table 2. Hydrogen bond geometry for (I) (Å, °).
D—H···AD—HH···AD···AD—H···A
C22—H22···O21i0.932.403.205 (3)144.4
C63—H63···O23ii0.932.553.425 (3)157.8
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+2, z+2.
Table 1. Comparison of the S2–N–O fragment in (I), (II), (III) top
CompoundN—S (Å)N—O (Å)O*—S (Å)S—N—O (°)S—N—S (°)
(I)1.728 (2)–1.728 (2)1.422 (2)1.675 (2)108.91 (14)–110.21 (14)125.43 (12)
(II)1.735 (2)–1.747 (3)1.419 (3)1.661 (2)107.87 (16)–110.64 (15)123.52 (14)
(III)1.715 (2)–1.753 (2)1.431 (2)1.649 (2)109.27 (14)–110.03 (13)119.64 (12)
Note: O* refers to the oxy group.
Table 3. ππ contacts (Å, °) for (I) and (II). top
CompoundGroup 1/Group 2ccd (Å)da (°)ipd (Å)
(I)
Cg1···Cg23.7810 (15)20.63 (13)3.59 (14)
Cg1···Cg2i4.3836 (16)9.13 (14)3.63 (36)
(II)
Cg1···Cg24.039 (2)32.67 (16)3.45 (50)
Cg1···Cg1ii3.957 (2)03.4794 (13)
Cg1 and Cg2 are the centroids of the C11/C21/C31/C41/C51/C61 and C12/C22/C32/C42/C52/C62 rings.

Symmetry codes: (i) x, -y+3/2, z-1/2; (ii) -x, -y+1, -z+1.

Notes: ccd is the center-to-center distance (distance between ring centroids); da is the dihedral angle between rings, ipd is the mean interplanar distance (distance from one plane to the neighbouring centroid). For details, see Janiak (2000).
 

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