1-Methyl-3-(4-methyl­phenyl­sulfonyl)-2-(4-methyl­phenyl­sulfonyl­imino)­benz­imidazole

The title compound, C₂₂H₂₁N₃O₄S₂, is the product of the nucleophilic attack on a tosyl chloride by 2-amino-1-methyl­benz­imidazole. The compound contains two tosyl groups, one directly attached to an imidazole ring nitro­gen and the other to the exocyclic N atom. The exocyclic N atom is bonded to the imidazole ring through a double bond [1.297 (3) Å]. The compound was also characterized by ¹H NMR spectroscopy.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.127
• Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.02
         From the CIF: _reflns_number_total               4641
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5151
         Completeness (_total/calc)             90.10%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

Our research group is interested in the synthesis and characterization of metal complexes of sulfonamides (Cabaleiro et al., 2000). These ligands are easily obtained by direct reaction of the corresponding amine and tosyl chloride. However, in the course of the reaction between tosylchloride and 2-amino-1-methylbenzimidazole, the title compound, (I), was obtained as the result of a double-tosylation on the amine group and on the nitrogen of the imidazole ring.

The 2-amino-1-methylbenzimidazole is usually considered to be an aromatic bicycle with an exocyclic amine group. However, the substitution of an amine hydrogen by an electron-withdrawing group causes the lack of aromaticity and the tautomeric displacement towards the imine form. Under these conditions, the substitution will be on the H atom of the imidazole ring nitrogen. The exocyclic nitrogen is bonded to the imidazole ring through a double bond, with a length of 1.297 (3) Å. This distance is shorter than those found in compounds with this skeleton, either organic (Benvenuti et al., 1995), or coordination compounds (Garnovskii et al., 1996). The imidazole ring is not aromatic, but its planarity is maintained due the sp² character of all five atoms (r.m.s. = 0.0151 Å). The exocyclic S2 and N1 atoms deviate from the best plane of the imidazole ring by 0.210 (1) and 0.086 (2) Å, respectively.

The two tosyl groups present in the compound are not equal, and the main difference lies on the sulfur environment. Focusing on the S—N bond, one of them has a bond distance of 1.6900 (19) Å, but the other one presents a value of 1.5896 (18) Å. The value expected for this kind of bond is around 1.64 Å (Allen et al., 1987). The shorter one corresponds to the tosyl group bonded to the exocyclic N and the conjugation probably plays an important role in the shortening of this bond. Indeed, assuming a value for a single N—S bond of 1.71 Å (Allen et al., 1987), the bond order could be calculated as 1.58 using the Pauling (1947) method (d_n-d = -0.60logn, where d_n is the bond length for bond order n, and d is the length of the single bond).

Although the H atoms have been included in their idealized positions, some of them are situated close to the sulfonyl O atoms, providing evidence for C—H···O hydrogen bonds (Taylor & Kennard, 1982) (Table 2). Similarly, some interactions between C—H groups and the π clouds of the rings are present in the compound. In Table 2, this interactions are set out, where Cg1 stands for the centroid of the imidazole ring, Cg2 for the centroid of the benzene ring C2–C7, Cg3 for the centroid of the phenyl ring C9–C14 and Cg4 for the centroid of the benzene ring C29–C214. The intramolecular interactions might be due to geometrical constraints, but intermolecular ones may be assumed to play a significant role in the packing arrangement.

S2. Experimental

The title compound was prepared by reaction of 2-amino-1-methylbenzimidazole (0.5 g, 3.4 mmol) and 4-methylphenylsulfonyl chloride (1.3 g, 6.8 mmol) in a 1:2 ratio in dichloromethane. A dilute aqueous solution of K₂CO₃ was added to the mixture until pH 10 was attained and the resultant white product collected by filtration of the organic phase and dried in vacuo. The product was recrystallized from CH₃CN/(CH₃)₂CO (1:1) to give crystals suitable for X-ray diffraction studies. The solid was identified by elemental analysis as the title compound. Found: C 57.5, H 4.9, N 9.3, S 14.0\5; calculated for C₂₂H₂₁N₃O₄S₂: C 58.0, H 4.6, N 9.2, S 14.1%. The ¹H NMR spectrum of the compound was recorded on a Bruker ARX-400 MHz s pectrophotometer in CDCl₃ solution against TMS as an internal reference. The spectrum shows three peaks as singlets at δ 2.35, 2.50 and 3.93 p.p.m. corresponding to the three methyl groups, whose C atoms were labeled as C15, C215 and C1, respectively. The signals corresponding to the aromatic rings appear between δ 6.95 and 8.25 p.p.m.

S3. Refinement

All H atoms in the molecule were refined using a riding model (HFIX 43 for aromatic and HFIX 137 for methyl groups).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1998); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level (Farrugia, 1998).

1-Methyl-3-(4-methylphenylsulfonyl)-2-(4-methylphenylsulfonylimino)benzimidazole

Crystal data

C22H21N3O4S2	Z = 2
Mr = 455.54	F(000) = 476
Triclinic, P1	Dx = 1.425 Mg m^−3
a = 7.9692 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1288 (11) Å	Cell parameters from 57 reflections
c = 13.5622 (13) Å	θ = 3–27°
α = 107.529 (2)°	µ = 0.29 mm^−1
β = 104.567 (2)°	T = 293 K
γ = 101.135 (2)°	Block, colourless
V = 1061.92 (18) Å^3	0.53 × 0.28 × 0.16 mm

Data collection

CCD area detector diffractometer	4641 independent reflections
Radiation source: fine-focus sealed tube	3401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 28.0°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.777, Tmax = 0.956	k = −14→13
6648 measured reflections	l = 0→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0685P)^2] where P = (Fo^2 + 2Fc^2)/3
4641 reflections	(Δ/σ)max = 0.004
283 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. We have measured to theta(max) = 28.02° with 90.1% completeness, but the data are virtually 95% complete to 25°

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.12729 (7)	0.25990 (5)	0.57943 (4)	0.03998 (16)
S2	−0.05559 (8)	0.12341 (6)	0.82726 (5)	0.04310 (17)
N1	0.0689 (3)	0.1812 (2)	0.65154 (15)	0.0476 (5)
N2	0.2770 (2)	0.04984 (16)	0.67270 (13)	0.0372 (4)
N3	0.0881 (2)	0.06266 (17)	0.76769 (14)	0.0390 (4)
O1	0.3164 (2)	0.32984 (17)	0.62160 (14)	0.0564 (5)
O11	−0.2011 (2)	0.12635 (17)	0.74388 (13)	0.0523 (4)
O22	−0.0881 (2)	0.04561 (17)	0.89057 (14)	0.0590 (5)
O2	0.0564 (2)	0.17681 (16)	0.46560 (12)	0.0566 (5)
C1	0.3574 (3)	0.0488 (2)	0.58711 (19)	0.0488 (6)
H1A	0.2644	0.0338	0.5203	0.073*
H1B	0.4149	−0.0201	0.5757	0.073*
H1C	0.4459	0.1322	0.6090	0.073*
C2	0.3140 (3)	−0.0210 (2)	0.74101 (17)	0.0412 (5)
C3	0.4389 (3)	−0.0902 (2)	0.7524 (2)	0.0548 (6)
H3	0.5133	−0.0982	0.7094	0.066*
C4	0.4491 (4)	−0.1468 (3)	0.8297 (2)	0.0673 (8)
H4	0.5322	−0.1941	0.8394	0.081*
C5	0.3379 (4)	−0.1349 (3)	0.8937 (2)	0.0629 (7)
H5	0.3497	−0.1733	0.9462	0.075*
C6	0.2105 (4)	−0.0681 (2)	0.88192 (19)	0.0526 (6)
H6	0.1354	−0.0612	0.9246	0.063*
C7	0.1995 (3)	−0.0115 (2)	0.80293 (17)	0.0406 (5)
C8	0.1440 (3)	0.1038 (2)	0.68986 (16)	0.0364 (5)
C9	0.0074 (3)	0.3769 (2)	0.60305 (16)	0.0391 (5)
C10	0.0957 (3)	0.5088 (2)	0.63734 (18)	0.0459 (5)
H10	0.2191	0.5365	0.6486	0.055*
C11	0.0000 (4)	0.6002 (2)	0.65505 (19)	0.0526 (6)
H11	0.0608	0.6891	0.6776	0.063*
C12	−0.1818 (4)	0.5635 (3)	0.64023 (19)	0.0518 (6)
C13	−0.2687 (4)	0.4298 (3)	0.6058 (2)	0.0607 (7)
H13	−0.3917	0.4022	0.5957	0.073*
C14	−0.1767 (3)	0.3372 (3)	0.5863 (2)	0.0571 (7)
H14	−0.2380	0.2482	0.5620	0.069*
C15	−0.2841 (4)	0.6631 (3)	0.6611 (3)	0.0739 (9)
H15A	−0.2205	0.7308	0.7321	0.111*
H15B	−0.4030	0.6207	0.6585	0.111*
H15C	−0.2944	0.7015	0.6061	0.111*
C29	0.0756 (3)	0.2835 (2)	0.91432 (17)	0.0408 (5)
C210	0.0734 (3)	0.3863 (2)	0.87804 (18)	0.0467 (6)
H210	−0.0041	0.3724	0.8091	0.056*
C211	0.1888 (3)	0.5111 (2)	0.94575 (19)	0.0515 (6)
H211	0.1876	0.5810	0.9218	0.062*
C212	0.3054 (3)	0.5329 (2)	1.04829 (18)	0.0499 (6)
C213	0.3018 (4)	0.4289 (3)	1.0832 (2)	0.0607 (7)
H213	0.3773	0.4431	1.1528	0.073*
C214	0.1887 (4)	0.3037 (3)	1.01752 (19)	0.0553 (6)
H214	0.1886	0.2342	1.0422	0.066*
C215	0.4326 (4)	0.6677 (3)	1.1211 (2)	0.0684 (8)
H21A	0.4187	0.7280	1.0839	0.103*
H21B	0.5552	0.6634	1.1381	0.103*
H21C	0.4048	0.6975	1.1876	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0411 (3)	0.0418 (3)	0.0393 (3)	0.0101 (2)	0.0151 (2)	0.0177 (2)
S2	0.0419 (3)	0.0475 (3)	0.0440 (3)	0.0120 (3)	0.0209 (3)	0.0176 (3)
N1	0.0546 (12)	0.0560 (12)	0.0535 (11)	0.0275 (10)	0.0296 (10)	0.0324 (10)
N2	0.0369 (10)	0.0357 (9)	0.0383 (9)	0.0108 (8)	0.0134 (8)	0.0116 (8)
N3	0.0469 (11)	0.0378 (10)	0.0388 (9)	0.0158 (8)	0.0202 (8)	0.0159 (8)
O1	0.0401 (10)	0.0558 (10)	0.0732 (11)	0.0116 (8)	0.0210 (8)	0.0233 (9)
O11	0.0395 (9)	0.0613 (11)	0.0534 (10)	0.0113 (8)	0.0147 (8)	0.0200 (8)
O22	0.0650 (12)	0.0643 (11)	0.0630 (11)	0.0162 (9)	0.0377 (9)	0.0321 (9)
O2	0.0758 (12)	0.0524 (10)	0.0387 (9)	0.0216 (9)	0.0166 (8)	0.0130 (8)
C1	0.0505 (14)	0.0525 (14)	0.0495 (13)	0.0189 (12)	0.0258 (12)	0.0171 (11)
C2	0.0392 (12)	0.0352 (11)	0.0431 (12)	0.0078 (10)	0.0079 (10)	0.0127 (10)
C3	0.0432 (14)	0.0536 (15)	0.0683 (16)	0.0185 (12)	0.0158 (12)	0.0230 (13)
C4	0.0634 (18)	0.0614 (17)	0.0789 (19)	0.0290 (14)	0.0092 (16)	0.0334 (15)
C5	0.0718 (19)	0.0551 (16)	0.0600 (16)	0.0182 (14)	0.0056 (14)	0.0324 (13)
C6	0.0643 (17)	0.0456 (14)	0.0476 (13)	0.0129 (12)	0.0158 (12)	0.0209 (11)
C7	0.0458 (13)	0.0335 (11)	0.0369 (11)	0.0092 (10)	0.0090 (10)	0.0106 (9)
C8	0.0396 (12)	0.0349 (11)	0.0326 (10)	0.0087 (9)	0.0128 (9)	0.0103 (9)
C9	0.0415 (12)	0.0397 (12)	0.0351 (11)	0.0086 (10)	0.0112 (9)	0.0154 (9)
C10	0.0418 (13)	0.0427 (13)	0.0494 (13)	0.0058 (10)	0.0123 (11)	0.0181 (11)
C11	0.0601 (17)	0.0434 (13)	0.0525 (14)	0.0141 (12)	0.0169 (12)	0.0173 (11)
C12	0.0645 (17)	0.0616 (16)	0.0451 (13)	0.0305 (14)	0.0260 (12)	0.0271 (12)
C13	0.0412 (14)	0.0703 (18)	0.0787 (18)	0.0177 (13)	0.0233 (13)	0.0347 (15)
C14	0.0457 (15)	0.0462 (14)	0.0745 (17)	0.0066 (12)	0.0170 (13)	0.0222 (13)
C15	0.093 (2)	0.086 (2)	0.081 (2)	0.0560 (19)	0.0522 (18)	0.0454 (18)
C29	0.0436 (13)	0.0453 (12)	0.0361 (11)	0.0173 (10)	0.0185 (10)	0.0113 (10)
C210	0.0513 (14)	0.0513 (14)	0.0365 (11)	0.0193 (11)	0.0140 (10)	0.0124 (10)
C211	0.0611 (16)	0.0455 (13)	0.0473 (13)	0.0177 (12)	0.0191 (12)	0.0139 (11)
C212	0.0485 (14)	0.0537 (15)	0.0405 (12)	0.0179 (12)	0.0160 (11)	0.0048 (11)
C213	0.0669 (18)	0.0661 (17)	0.0379 (13)	0.0226 (14)	0.0061 (12)	0.0113 (12)
C214	0.0662 (17)	0.0590 (16)	0.0422 (13)	0.0246 (13)	0.0147 (12)	0.0196 (12)
C215	0.0605 (18)	0.0615 (18)	0.0592 (16)	0.0120 (14)	0.0111 (14)	0.0001 (14)

Geometric parameters (Å, º)

S1—O1	1.4319 (16)	C9—C14	1.386 (3)
S1—O2	1.4342 (16)	C10—C11	1.385 (3)
S1—N1	1.5896 (18)	C10—H10	0.93
S1—C9	1.759 (2)	C11—C12	1.372 (3)
S2—O11	1.4148 (16)	C11—H11	0.93
S2—O22	1.4238 (17)	C12—C13	1.390 (4)
S2—N3	1.6900 (19)	C12—C15	1.500 (4)
S2—C29	1.747 (2)	C13—C14	1.375 (4)
N1—C8	1.297 (3)	C13—H13	0.93
N2—C8	1.351 (3)	C14—H14	0.93
N2—C2	1.399 (3)	C15—H15A	0.96
N2—C1	1.458 (3)	C15—H15B	0.96
N3—C8	1.404 (3)	C15—H15C	0.96
N3—C7	1.416 (3)	C29—C210	1.376 (3)
C1—H1A	0.96	C29—C214	1.386 (3)
C1—H1B	0.96	C210—C211	1.389 (3)
C1—H1C	0.96	C210—H210	0.93
C2—C3	1.378 (3)	C211—C212	1.384 (3)
C2—C7	1.385 (3)	C211—H211	0.93
C3—C4	1.370 (4)	C212—C213	1.375 (4)
C3—H3	0.93	C212—C215	1.506 (3)
C4—C5	1.385 (4)	C213—C214	1.382 (4)
C4—H4	0.93	C213—H213	0.93
C5—C6	1.374 (4)	C214—H214	0.93
C5—H5	0.93	C215—H21A	0.96
C6—C7	1.390 (3)	C215—H21B	0.96
C6—H6	0.93	C215—H21C	0.96
C9—C10	1.376 (3)
O1—S1—O2	116.39 (11)	C10—C9—S1	120.09 (18)
O1—S1—N1	112.76 (10)	C14—C9—S1	120.49 (18)
O2—S1—N1	110.34 (11)	C9—C10—C11	119.7 (2)
O1—S1—C9	107.62 (10)	C9—C10—H10	120.1
O2—S1—C9	108.91 (10)	C11—C10—H10	120.1
N1—S1—C9	99.34 (10)	C12—C11—C10	121.9 (2)
O11—S2—O22	120.35 (11)	C12—C11—H11	119.0
O11—S2—N3	107.70 (9)	C10—C11—H11	119.0
O22—S2—N3	104.02 (10)	C11—C12—C13	117.5 (2)
O11—S2—C29	110.36 (11)	C11—C12—C15	121.7 (3)
O22—S2—C29	109.66 (11)	C13—C12—C15	120.8 (3)
N3—S2—C29	103.17 (10)	C14—C13—C12	121.5 (2)
C8—N1—S1	129.56 (17)	C14—C13—H13	119.3
C8—N2—C2	110.05 (18)	C12—C13—H13	119.3
C8—N2—C1	126.40 (18)	C13—C14—C9	119.9 (2)
C2—N2—C1	123.12 (19)	C13—C14—H14	120.0
C8—N3—C7	108.79 (18)	C9—C14—H14	120.0
C8—N3—S2	123.26 (15)	C12—C15—H15A	109.5
C7—N3—S2	126.58 (15)	C12—C15—H15B	109.5
N2—C1—H1A	109.5	H15A—C15—H15B	109.5
N2—C1—H1B	109.5	C12—C15—H15C	109.5
H1A—C1—H1B	109.5	H15A—C15—H15C	109.5
N2—C1—H1C	109.5	H15B—C15—H15C	109.5
H1A—C1—H1C	109.5	C210—C29—C214	120.8 (2)
H1B—C1—H1C	109.5	C210—C29—S2	120.10 (17)
C3—C2—C7	121.6 (2)	C214—C29—S2	118.98 (19)
C3—C2—N2	130.3 (2)	C29—C210—C211	119.1 (2)
C7—C2—N2	108.1 (2)	C29—C210—H210	120.5
C4—C3—C2	117.4 (3)	C211—C210—H210	120.5
C4—C3—H3	121.3	C212—C211—C210	121.0 (2)
C2—C3—H3	121.3	C212—C211—H211	119.5
C3—C4—C5	121.2 (3)	C210—C211—H211	119.5
C3—C4—H4	119.4	C213—C212—C211	118.5 (2)
C5—C4—H4	119.4	C213—C212—C215	120.4 (2)
C6—C5—C4	122.1 (2)	C211—C212—C215	121.1 (2)
C6—C5—H5	119.0	C212—C213—C214	121.7 (2)
C4—C5—H5	119.0	C212—C213—H213	119.2
C5—C6—C7	116.6 (3)	C214—C213—H213	119.2
C5—C6—H6	121.7	C213—C214—C29	118.8 (2)
C7—C6—H6	121.7	C213—C214—H214	120.6
C2—C7—C6	121.1 (2)	C29—C214—H214	120.6
C2—C7—N3	106.10 (18)	C212—C215—H21A	109.5
C6—C7—N3	132.8 (2)	C212—C215—H21B	109.5
N1—C8—N2	133.5 (2)	H21A—C215—H21B	109.5
N1—C8—N3	119.6 (2)	C212—C215—H21C	109.5
N2—C8—N3	106.85 (17)	H21A—C215—H21C	109.5
C10—C9—C14	119.4 (2)	H21B—C215—H21C	109.5
O1—S1—N1—C8	−47.6 (2)	S2—N3—C8—N1	−7.8 (3)
O2—S1—N1—C8	84.4 (2)	C7—N3—C8—N2	3.7 (2)
C9—S1—N1—C8	−161.3 (2)	S2—N3—C8—N2	171.15 (14)
O11—S2—N3—C8	45.53 (19)	O1—S1—C9—C10	10.7 (2)
O22—S2—N3—C8	174.32 (16)	O2—S1—C9—C10	−116.29 (18)
C29—S2—N3—C8	−71.19 (18)	N1—S1—C9—C10	128.33 (19)
O11—S2—N3—C7	−149.34 (17)	O1—S1—C9—C14	−169.92 (18)
O22—S2—N3—C7	−20.5 (2)	O2—S1—C9—C14	63.1 (2)
C29—S2—N3—C7	93.94 (19)	N1—S1—C9—C14	−52.3 (2)
C8—N2—C2—C3	−179.2 (2)	C14—C9—C10—C11	0.2 (3)
C1—N2—C2—C3	7.8 (4)	S1—C9—C10—C11	179.57 (17)
C8—N2—C2—C7	0.2 (2)	C9—C10—C11—C12	0.5 (4)
C1—N2—C2—C7	−172.69 (19)	C10—C11—C12—C13	−0.4 (4)
C7—C2—C3—C4	−1.7 (4)	C10—C11—C12—C15	179.1 (2)
N2—C2—C3—C4	177.7 (2)	C11—C12—C13—C14	−0.5 (4)
C2—C3—C4—C5	0.1 (4)	C15—C12—C13—C14	−180.0 (2)
C3—C4—C5—C6	1.1 (4)	C12—C13—C14—C9	1.2 (4)
C4—C5—C6—C7	−0.6 (4)	C10—C9—C14—C13	−1.1 (4)
C3—C2—C7—C6	2.2 (3)	S1—C9—C14—C13	179.6 (2)
N2—C2—C7—C6	−177.4 (2)	O11—S2—C29—C210	−22.8 (2)
C3—C2—C7—N3	−178.4 (2)	O22—S2—C29—C210	−157.65 (19)
N2—C2—C7—N3	2.0 (2)	N3—S2—C29—C210	92.0 (2)
C5—C6—C7—C2	−1.0 (3)	O11—S2—C29—C214	160.82 (18)
C5—C6—C7—N3	179.8 (2)	O22—S2—C29—C214	26.0 (2)
C8—N3—C7—C2	−3.6 (2)	N3—S2—C29—C214	−84.4 (2)
S2—N3—C7—C2	−170.45 (15)	C214—C29—C210—C211	1.0 (4)
C8—N3—C7—C6	175.7 (2)	S2—C29—C210—C211	−175.29 (18)
S2—N3—C7—C6	8.8 (4)	C29—C210—C211—C212	0.3 (4)
S1—N1—C8—N2	−9.8 (4)	C210—C211—C212—C213	−1.6 (4)
S1—N1—C8—N3	168.85 (16)	C210—C211—C212—C215	179.0 (2)
C2—N2—C8—N1	176.3 (2)	C211—C212—C213—C214	1.7 (4)
C1—N2—C8—N1	−11.0 (4)	C215—C212—C213—C214	−178.9 (2)
C2—N2—C8—N3	−2.4 (2)	C212—C213—C214—C29	−0.5 (4)
C1—N2—C8—N3	170.20 (19)	C210—C29—C214—C213	−0.9 (4)
C7—N3—C8—N1	−175.25 (19)	S2—C29—C214—C213	175.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···O1	0.96	2.58	3.114 (3)	115
C6—H6···O22	0.93	2.35	2.914 (3)	119
C10—H10···O1	0.93	2.52	2.897 (3)	105
C6—H6···O22^i	0.93	2.59	3.417 (3)	149
C13—H13···O1^ii	0.93	2.46	3.361 (3)	164
C210—H210···Cg3	0.93	3.03	3.844 (3)	147
C11—H11···Cg2^iii	0.93	2.76	3.624 (3)	154
C215—H21B···Cg1^iv	0.96	3.19	3.551 (3)	104
C215—H21B···Cg4^iv	0.96	2.98	3.756 (3)	138

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