Bis(4-methyl­phenyl­sulfon­yl)amino 4-methyl­benzene­sulfonate: a new member of the (RSO₂)ON(SO₂R)₂ family

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.

S1. Comment

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 π–π 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 π–π 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 π–π 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 π–π 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 π–π 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-CH<sub>3</sub> 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)<sub>methyl</sub>···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

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).

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.5U_eq(C), and for aromatic H atoms, C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

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

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 40% probability level.
	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.
	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

Crystal data

C21H21NO7S3	F(000) = 1032
Mr = 495.57	Dx = 1.424 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4103 reflections
a = 14.6523 (6) Å	θ = 3.7–28.8°
b = 9.9342 (5) Å	µ = 0.36 mm^−1
c = 16.0953 (6) Å	T = 295 K
β = 99.355 (4)°	Prisms, colourless
V = 2311.65 (17) Å^3	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	5389 independent reflections
Radiation source: fine-focus sealed tube	2771 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
ω scans, thick slices	θmax = 28.8°, θmin = 3.7°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −19→19
Tmin = 0.945, Tmax = 0.952	k = −13→13
15723 measured reflections	l = −20→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.486P] where P = (Fo^2 + 2Fc^2)/3
5389 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.20 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.64217 (5)	1.05279 (8)	0.84217 (4)	0.0590 (2)
S2	0.70071 (5)	1.03700 (7)	1.03406 (4)	0.05370 (19)
S3	0.88243 (5)	1.17019 (8)	0.92356 (4)	0.0583 (2)
O11	0.68307 (14)	1.1219 (2)	0.78017 (11)	0.0757 (6)
O21	0.55578 (12)	1.0922 (2)	0.86219 (12)	0.0747 (6)
O12	0.61333 (12)	1.09443 (18)	1.04105 (11)	0.0644 (5)
O22	0.78335 (12)	1.08180 (19)	1.08539 (11)	0.0666 (5)
O13	0.83000 (14)	1.29006 (19)	0.91856 (12)	0.0741 (6)
O23	0.95277 (12)	1.1446 (2)	0.99318 (11)	0.0763 (6)
N1	0.71880 (13)	1.0808 (2)	0.93407 (12)	0.0516 (5)
C11	0.64351 (18)	0.8815 (3)	0.82238 (15)	0.0535 (7)
C21	0.5743 (2)	0.8003 (3)	0.84448 (16)	0.0642 (8)
H21	0.5266	0.8371	0.8689	0.077*
C31	0.5776 (2)	0.6633 (4)	0.82941 (18)	0.0760 (9)
H31	0.5314	0.6079	0.8437	0.091*
C41	0.6481 (3)	0.6076 (4)	0.79354 (19)	0.0793 (10)
C51	0.7144 (2)	0.6914 (4)	0.77068 (19)	0.0790 (10)
H51	0.7611	0.6548	0.7449	0.095*
C61	0.7136 (2)	0.8264 (3)	0.78470 (16)	0.0692 (8)
H61	0.7596	0.8811	0.7692	0.083*
C71	0.6501 (3)	0.4576 (4)	0.7794 (2)	0.1166 (14)
H71A	0.6454	0.4396	0.7202	0.175*
H71B	0.5991	0.4163	0.8003	0.175*
H71C	0.7072	0.4214	0.8086	0.175*
C12	0.69481 (17)	0.8623 (3)	1.03894 (14)	0.0481 (6)
C22	0.61244 (19)	0.8027 (3)	1.05039 (15)	0.0580 (7)
H22	0.5605	0.8551	1.0534	0.070*
C32	0.6082 (2)	0.6651 (3)	1.05717 (16)	0.0668 (8)
H32	0.5531	0.6255	1.0661	0.080*
C42	0.6830 (2)	0.5841 (3)	1.05120 (16)	0.0646 (8)
C52	0.7645 (2)	0.6458 (3)	1.03959 (18)	0.0725 (9)
H52	0.8159	0.5927	1.0354	0.087*
C62	0.77195 (18)	0.7825 (3)	1.03406 (17)	0.0655 (8)
H62	0.8278	0.8218	1.0271	0.079*
C72	0.6760 (2)	0.4331 (3)	1.0568 (2)	0.0937 (11)
H72A	0.6706	0.4079	1.1134	0.141*
H72B	0.7305	0.3927	1.0416	0.141*
H72C	0.6225	0.4026	1.0191	0.141*
C13	0.92562 (17)	1.1392 (3)	0.83080 (15)	0.0509 (6)
C23	0.88491 (19)	1.1969 (3)	0.75569 (17)	0.0638 (8)
H23	0.8313	1.2479	0.7531	0.077*
C33	0.9245 (2)	1.1781 (3)	0.68498 (16)	0.0684 (8)
H33	0.8978	1.2184	0.6347	0.082*
C43	1.0027 (2)	1.1010 (3)	0.68671 (17)	0.0644 (8)
C53	1.04090 (19)	1.0425 (3)	0.76170 (17)	0.0686 (8)
H53	1.0935	0.9894	0.7637	0.082*
C63	1.00350 (18)	1.0603 (3)	0.83377 (16)	0.0608 (7)
H63	1.0303	1.0198	0.8839	0.073*
C73	1.0461 (2)	1.0825 (4)	0.60865 (18)	0.1033 (13)
H73A	1.0743	1.1654	0.5955	0.155*
H73B	0.9994	1.0570	0.5624	0.155*
H73C	1.0924	1.0133	0.6184	0.155*
O33	0.80876 (11)	1.04082 (17)	0.92177 (10)	0.0543 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0591 (4)	0.0663 (5)	0.0511 (4)	0.0075 (4)	0.0073 (3)	0.0033 (4)
S2	0.0558 (4)	0.0581 (4)	0.0492 (4)	0.0018 (4)	0.0144 (3)	−0.0024 (3)
S3	0.0619 (4)	0.0613 (5)	0.0542 (4)	−0.0092 (4)	0.0168 (3)	−0.0041 (4)
O11	0.0903 (14)	0.0822 (15)	0.0552 (11)	−0.0033 (11)	0.0140 (10)	0.0149 (10)
O21	0.0580 (12)	0.0880 (15)	0.0770 (13)	0.0228 (11)	0.0074 (10)	−0.0018 (11)
O12	0.0630 (12)	0.0654 (13)	0.0703 (12)	0.0135 (10)	0.0276 (10)	−0.0025 (10)
O22	0.0672 (12)	0.0775 (14)	0.0534 (10)	−0.0118 (10)	0.0052 (9)	−0.0075 (10)
O13	0.0844 (14)	0.0528 (13)	0.0927 (14)	−0.0022 (11)	0.0371 (11)	−0.0049 (11)
O23	0.0689 (12)	0.1063 (17)	0.0517 (11)	−0.0163 (12)	0.0038 (10)	−0.0085 (11)
N1	0.0451 (12)	0.0591 (14)	0.0530 (12)	0.0032 (11)	0.0149 (10)	0.0018 (10)
C11	0.0534 (16)	0.0668 (19)	0.0392 (14)	0.0062 (15)	0.0040 (12)	−0.0057 (13)
C21	0.0567 (18)	0.079 (2)	0.0550 (16)	−0.0031 (16)	0.0034 (13)	−0.0052 (16)
C31	0.088 (2)	0.072 (2)	0.0615 (19)	−0.020 (2)	−0.0054 (17)	−0.0009 (18)
C41	0.097 (3)	0.076 (2)	0.0561 (19)	0.017 (2)	−0.0143 (18)	−0.0110 (18)
C51	0.080 (2)	0.090 (3)	0.065 (2)	0.021 (2)	0.0092 (17)	−0.0172 (19)
C61	0.069 (2)	0.083 (2)	0.0567 (17)	0.0016 (18)	0.0134 (14)	−0.0079 (17)
C71	0.156 (4)	0.079 (3)	0.100 (3)	0.016 (3)	−0.024 (2)	−0.018 (2)
C12	0.0481 (16)	0.0569 (17)	0.0399 (13)	0.0023 (13)	0.0088 (11)	0.0023 (12)
C22	0.0535 (17)	0.060 (2)	0.0619 (17)	0.0070 (14)	0.0129 (13)	0.0023 (14)
C32	0.0641 (19)	0.071 (2)	0.0679 (19)	−0.0089 (17)	0.0190 (15)	0.0021 (17)
C42	0.082 (2)	0.060 (2)	0.0542 (17)	0.0031 (17)	0.0185 (15)	0.0020 (14)
C52	0.072 (2)	0.065 (2)	0.087 (2)	0.0227 (17)	0.0287 (17)	0.0115 (17)
C62	0.0497 (18)	0.071 (2)	0.078 (2)	0.0124 (15)	0.0179 (15)	0.0100 (16)
C72	0.127 (3)	0.064 (2)	0.094 (2)	0.005 (2)	0.030 (2)	0.0081 (19)
C13	0.0491 (15)	0.0562 (17)	0.0482 (14)	−0.0017 (13)	0.0100 (12)	0.0044 (13)
C23	0.0570 (17)	0.072 (2)	0.0650 (18)	0.0173 (15)	0.0167 (14)	0.0163 (15)
C33	0.073 (2)	0.084 (2)	0.0482 (16)	0.0168 (18)	0.0082 (14)	0.0168 (16)
C43	0.0658 (18)	0.075 (2)	0.0555 (17)	0.0161 (16)	0.0179 (14)	0.0067 (15)
C53	0.0636 (18)	0.077 (2)	0.0684 (18)	0.0247 (17)	0.0207 (15)	0.0139 (17)
C63	0.0524 (16)	0.077 (2)	0.0524 (15)	0.0090 (15)	0.0076 (13)	0.0172 (15)
C73	0.113 (3)	0.145 (4)	0.0572 (19)	0.051 (3)	0.0297 (18)	0.012 (2)
O33	0.0540 (10)	0.0541 (11)	0.0584 (10)	−0.0013 (9)	0.0201 (8)	0.0000 (9)

Geometric parameters (Å, º)

S1—O21	1.4115 (19)	C12—C62	1.393 (3)
S1—O11	1.4214 (19)	C22—C32	1.373 (4)
S1—N1	1.728 (2)	C22—H22	0.9300
S1—C11	1.732 (3)	C32—C42	1.376 (4)
S2—O22	1.4218 (18)	C32—H32	0.9300
S2—O12	1.4228 (17)	C42—C52	1.382 (4)
S2—N1	1.729 (2)	C42—C72	1.507 (4)
S2—C12	1.740 (3)	C52—C62	1.367 (4)
S3—O13	1.412 (2)	C52—H52	0.9300
S3—O23	1.4167 (19)	C62—H62	0.9300
S3—O33	1.6756 (18)	C72—H72A	0.9600
S3—C13	1.741 (2)	C72—H72B	0.9600
N1—O33	1.421 (2)	C72—H72C	0.9600
C11—C21	1.387 (4)	C13—C63	1.379 (3)
C11—C61	1.388 (4)	C13—C23	1.383 (3)
C21—C31	1.385 (4)	C23—C33	1.371 (4)
C21—H21	0.9300	C23—H23	0.9300
C31—C41	1.379 (4)	C33—C43	1.376 (4)
C31—H31	0.9300	C33—H33	0.9300
C41—C51	1.375 (5)	C43—C53	1.374 (4)
C41—C71	1.508 (5)	C43—C73	1.509 (4)
C51—C61	1.360 (4)	C53—C63	1.372 (3)
C51—H51	0.9300	C53—H53	0.9300
C61—H61	0.9300	C63—H63	0.9300
C71—H71A	0.9600	C73—H73A	0.9600
C71—H71B	0.9600	C73—H73B	0.9600
C71—H71C	0.9600	C73—H73C	0.9600
C12—C22	1.383 (3)
O21—S1—O11	121.48 (13)	C62—C12—S2	121.2 (2)
O21—S1—N1	104.00 (11)	C32—C22—C12	119.2 (3)
O11—S1—N1	103.52 (11)	C32—C22—H22	120.4
O21—S1—C11	110.62 (13)	C12—C22—H22	120.4
O11—S1—C11	109.07 (13)	C22—C32—C42	122.0 (3)
N1—S1—C11	106.88 (11)	C22—C32—H32	119.0
O22—S2—O12	121.39 (11)	C42—C32—H32	119.0
O22—S2—N1	102.55 (10)	C32—C42—C52	117.8 (3)
O12—S2—N1	104.41 (10)	C32—C42—C72	121.0 (3)
O22—S2—C12	109.26 (12)	C52—C42—C72	121.2 (3)
O12—S2—C12	110.14 (12)	C62—C52—C42	122.0 (3)
N1—S2—C12	108.01 (11)	C62—C52—H52	119.0
O13—S3—O23	121.02 (13)	C42—C52—H52	119.0
O13—S3—O33	107.63 (10)	C52—C62—C12	119.2 (3)
O23—S3—O33	105.06 (11)	C52—C62—H62	120.4
O13—S3—C13	111.73 (12)	C12—C62—H62	120.4
O23—S3—C13	109.12 (12)	C42—C72—H72A	109.5
O33—S3—C13	99.95 (10)	C42—C72—H72B	109.5
O33—N1—S1	108.91 (14)	H72A—C72—H72B	109.5
O33—N1—S2	110.21 (14)	C42—C72—H72C	109.5
S1—N1—S2	125.43 (12)	H72A—C72—H72C	109.5
C21—C11—C61	120.5 (3)	H72B—C72—H72C	109.5
C21—C11—S1	119.6 (2)	C63—C13—C23	120.2 (2)
C61—C11—S1	119.9 (2)	C63—C13—S3	119.0 (2)
C31—C21—C11	118.6 (3)	C23—C13—S3	120.8 (2)
C31—C21—H21	120.7	C33—C23—C13	119.3 (2)
C11—C21—H21	120.7	C33—C23—H23	120.4
C41—C31—C21	121.2 (3)	C13—C23—H23	120.4
C41—C31—H31	119.4	C23—C33—C43	121.5 (2)
C21—C31—H31	119.4	C23—C33—H33	119.3
C51—C41—C31	118.6 (3)	C43—C33—H33	119.3
C51—C41—C71	121.7 (4)	C53—C43—C33	118.2 (3)
C31—C41—C71	119.7 (4)	C53—C43—C73	120.9 (3)
C61—C51—C41	121.9 (3)	C33—C43—C73	120.9 (3)
C61—C51—H51	119.1	C63—C53—C43	121.8 (3)
C41—C51—H51	119.1	C63—C53—H53	119.1
C51—C61—C11	119.2 (3)	C43—C53—H53	119.1
C51—C61—H61	120.4	C53—C63—C13	119.1 (2)
C11—C61—H61	120.4	C53—C63—H63	120.5
C41—C71—H71A	109.5	C13—C63—H63	120.5
C41—C71—H71B	109.5	C43—C73—H73A	109.5
H71A—C71—H71B	109.5	C43—C73—H73B	109.5
C41—C71—H71C	109.5	H73A—C73—H73B	109.5
H71A—C71—H71C	109.5	C43—C73—H73C	109.5
H71B—C71—H71C	109.5	H73A—C73—H73C	109.5
C22—C12—C62	119.8 (3)	H73B—C73—H73C	109.5
C22—C12—S2	118.9 (2)	N1—O33—S3	113.13 (14)

Hydrogen-bond geometry (Å, º)

Table 2. Hydrogen bond geometry for (I) (Å, °).

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O21^i	0.93	2.40	3.205 (3)	144
C63—H63···O23^ii	0.93	2.55	3.425 (3)	158

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