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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1218.
Published online 2010 April 30. doi:  10.1107/S1600536810015059
PMCID: PMC2979169

N,N-Dibenzyl-4-methyl­benzene­sulfonamide

Abstract

The asymmetric unit of the title compound, C21H21NO2S, comprises two mol­ecules with similar conformations. The benzene rings of the nitro­gen-bound benzyl groups lie to the same side of the mol­ecule but are splayed in opposite directions precluding π–π inter­actions between them. In the crystal, each independent mol­ecule self-associates via inter­molecular C—H(...)O inter­actions, forming a supra­molecular chain propagating along the b axis.

Related literature

For related structures, see: Khan et al. (2010 [triangle]); Arshad et al. (2009 [triangle]).

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Object name is e-66-o1218-scheme1.jpg

Experimental

Crystal data

  • C21H21NO2S
  • M r = 351.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1218-efi1.jpg
  • a = 27.7716 (15) Å
  • b = 5.9523 (3) Å
  • c = 22.3140 (12) Å
  • V = 3688.6 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 293 K
  • 0.39 × 0.11 × 0.07 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 51453 measured reflections
  • 6474 independent reflections
  • 3191 reflections with I > 2σ(I)
  • R int = 0.122

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.232
  • S = 1.02
  • 6474 reflections
  • 453 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.35 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3144 Friedel pairs
  • Flack parameter: 0.18 (17)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), QMol (Gans & Shalloway, 2001 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015059/hb5415sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015059/hb5415Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are thankful to Mr Munawar Hussain, Engineering Cell, GC University, Lahore, for providing support services to the Materials Chemistry Laboratory.

supplementary crystallographic information

Comment

The title compound, (I), was investigated as an extension of previously reported studies (Khan et al., 2010; Arshad et al., 2009). Two independent molecules comprise the crystallographic asymmetric unit of (I), Figs 1 and 2. The conformations are very similar to each other with the inverted form of the first molecule being virtually superimposable on the second independent molecule, Fig. 3. This similarity is quantified in the r.m.s. values for bond distances and angles of 0.0316 Å and 1.717 °, respectively. In terms of the molecular conformation, the benzene rings of the benzyl groups are orientated in the same direction but are splayed somewhat so that there is no evidence of a π–π interaction between them [the dihedral angle between the C9–C14 and C16–C21 rings is 33.6 (5) °; 28.5 (5) ° for the dihedral angle between C30–C35 and C37–C42 rings in the second independent molecule]. The tolyl group is twisted out of the putative mirror plane bisecting the benzyl rings and containing the NS–Ctolyl moiety as seen in the values of the N1–S1–C1–C2 and N2–S2–C22–C23 torsion angles of -27.9 (7) and -147.7 (6) °, respectively.

Each independent molecule self-associates into a supramolecular chain along the b axis that is sustained by C–H···O contacts, Table 1. A view of one such chain is shown in Fig. 4.

Experimental

A mixture of N-benzyl-4-methylbenzenesulfonamide (0.5 g, 2.02 mmol), sodium hydride (0.2 g, 8.333 mmol) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min. followed by the addition of benzyl chloride (0.23 ml, 2.02 mmol). After complete consumption of reactants (as monitored by TLC), the contents were poured over crushed ice. The precipitated product was isolated, washed and recrystallized from methanol solution to yield colourless blocks of (I).

Refinement

The H atoms were geometrically placed (C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of the first independent molecule in (I) showing displacement ellipsoids at the 35% probability level.
Fig. 2.
The molecular structure of the second independent molecule in (I) showing displacement ellipsoids at the 35% probability level.
Fig. 3.
Overlap diagram highlighting the different conformations of the first (red) and second (blue) independent molecules in (I).
Fig. 4.
A view of a supramolecular chain in (I) formed by the first independent molecule aligned along the b axis. The C–H···O contacts are shown as orange dashed lines. Colour code: S, yellow; O, red; N, blue; C, grey; and H, ...

Crystal data

C21H21NO2SF(000) = 1488
Mr = 351.45Dx = 1.266 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1938 reflections
a = 27.7716 (15) Åθ = 2.3–23.9°
b = 5.9523 (3) ŵ = 0.19 mm1
c = 22.3140 (12) ÅT = 293 K
V = 3688.6 (3) Å3Block, colourless
Z = 80.39 × 0.11 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer3191 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.122
graphiteθmax = 25.0°, θmin = 1.5°
[var phi] and ω scansh = −33→33
51453 measured reflectionsk = −7→6
6474 independent reflectionsl = −26→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.232w = 1/[σ2(Fo2) + (0.1204P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
6474 reflectionsΔρmax = 0.31 e Å3
453 parametersΔρmin = −0.35 e Å3
1 restraintAbsolute structure: Flack (1983), 3144 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.18 (17)

Special details

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)

xyzUiso*/Ueq
S10.92190 (7)0.3770 (3)0.10735 (10)0.0630 (6)
O10.9371 (2)0.2775 (9)0.0517 (3)0.0870 (19)
O20.9176 (2)0.2351 (9)0.1592 (3)0.0848 (17)
N10.95928 (19)0.5761 (9)0.1242 (3)0.0587 (17)
C10.8657 (2)0.5026 (11)0.0928 (3)0.058 (2)
C20.8521 (3)0.6993 (12)0.1184 (4)0.070 (2)
H20.87300.77590.14380.084*
C30.8066 (3)0.7853 (13)0.1061 (4)0.069 (2)
H30.79820.92570.12110.083*
C40.7749 (3)0.6720 (14)0.0735 (4)0.071 (2)
C50.7891 (3)0.4704 (15)0.0470 (4)0.079 (2)
H50.76780.39080.02290.095*
C60.8337 (3)0.3923 (14)0.0565 (4)0.076 (2)
H60.84320.25960.03790.091*
C70.7245 (3)0.7664 (17)0.0596 (4)0.098 (3)
H7A0.70070.68150.08110.148*
H7B0.71840.75560.01740.148*
H7C0.72300.92100.07170.148*
C80.9737 (3)0.7298 (12)0.0754 (4)0.073 (2)
H8A0.96250.88010.08470.087*
H8B0.95820.68270.03850.087*
C91.0275 (3)0.7360 (11)0.0659 (3)0.059 (2)
C101.0507 (3)0.5595 (13)0.0392 (4)0.073 (2)
H101.03330.43320.02750.088*
C111.0993 (4)0.5681 (16)0.0296 (4)0.086 (3)
H111.11500.44590.01240.103*
C121.1244 (4)0.752 (2)0.0447 (5)0.089 (3)
H121.15730.75600.03670.107*
C131.1041 (4)0.9255 (19)0.0706 (5)0.098 (3)
H131.12251.04880.08190.117*
C141.0545 (4)0.9232 (12)0.0808 (4)0.084 (3)
H141.03961.04780.09780.101*
C150.9642 (3)0.6567 (13)0.1858 (4)0.073 (2)
H15A0.94180.57570.21120.087*
H15B0.95570.81460.18720.087*
C161.0142 (3)0.6280 (13)0.2104 (3)0.062 (2)
C171.0412 (3)0.4396 (14)0.2004 (4)0.084 (3)
H171.02890.32360.17710.101*
C181.0867 (4)0.4208 (19)0.2247 (5)0.105 (3)
H181.10540.29510.21620.126*
C191.1038 (4)0.579 (2)0.2598 (5)0.107 (3)
H191.13400.56010.27730.129*
C201.0794 (5)0.762 (2)0.2706 (5)0.112 (4)
H201.09300.87420.29420.135*
C211.0328 (4)0.7916 (15)0.2468 (4)0.092 (3)
H211.01510.91970.25570.110*
S20.61516 (7)−0.1198 (3)0.85180 (11)0.0668 (6)
O30.6084 (2)−0.2503 (10)0.7995 (3)0.099 (2)
O40.6322 (2)−0.2288 (9)0.9045 (3)0.0878 (18)
N20.65232 (19)0.0765 (9)0.8363 (2)0.0564 (16)
C220.5594 (3)0.0061 (12)0.8705 (3)0.061 (2)
C230.5302 (3)−0.0963 (13)0.9120 (4)0.080 (3)
H230.5399−0.22770.93100.096*
C240.4862 (3)−0.0013 (16)0.9251 (4)0.086 (3)
H240.4664−0.07180.95290.103*
C250.4706 (3)0.1944 (15)0.8985 (4)0.072 (2)
C260.5017 (3)0.2958 (14)0.8591 (5)0.090 (3)
H260.49270.43040.84110.108*
C270.5448 (3)0.2057 (13)0.8459 (4)0.083 (3)
H270.56520.28050.81940.100*
C280.4230 (3)0.297 (2)0.9128 (5)0.117 (4)
H28A0.42780.43230.93540.176*
H28B0.40420.19290.93600.176*
H28C0.40630.33130.87630.176*
C290.6577 (3)0.1596 (13)0.7761 (4)0.073 (2)
H29A0.64980.31840.77570.088*
H29B0.63470.08320.75060.088*
C300.7073 (3)0.1295 (13)0.7501 (3)0.060 (2)
C310.7283 (4)0.2922 (14)0.7144 (4)0.081 (3)
H310.71150.42400.70640.097*
C320.7737 (4)0.2633 (19)0.6904 (5)0.105 (3)
H320.78680.37280.66570.125*
C330.7993 (4)0.071 (2)0.7034 (5)0.102 (3)
H330.83040.05290.68880.122*
C340.7786 (4)−0.0930 (19)0.7379 (5)0.103 (3)
H340.7953−0.22520.74580.124*
C350.7336 (3)−0.0629 (14)0.7607 (4)0.080 (3)
H350.7202−0.17570.78420.096*
C360.6680 (3)0.2290 (12)0.8854 (4)0.070 (2)
H36A0.65770.38090.87640.084*
H36B0.65260.18350.92250.084*
C370.7209 (3)0.2269 (13)0.8937 (4)0.063 (2)
C380.7496 (4)0.4127 (12)0.8793 (4)0.083 (3)
H380.73500.54420.86580.099*
C390.7983 (4)0.4037 (18)0.8846 (5)0.096 (3)
H390.81630.52840.87350.115*
C400.8216 (4)0.218 (2)0.9058 (5)0.098 (3)
H400.85500.21380.90870.118*
C410.7942 (4)0.0384 (16)0.9226 (4)0.088 (3)
H410.8090−0.08870.93830.105*
C420.7448 (3)0.0437 (12)0.9164 (4)0.071 (2)
H420.7270−0.08140.92800.086*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0686 (13)0.0448 (9)0.0757 (14)0.0117 (9)0.0100 (11)0.0011 (12)
O10.079 (4)0.076 (4)0.106 (5)0.013 (3)0.006 (4)−0.039 (4)
O20.083 (4)0.061 (3)0.110 (5)0.006 (3)0.008 (3)0.019 (4)
N10.056 (4)0.049 (3)0.071 (5)−0.001 (3)−0.001 (3)0.005 (3)
C10.056 (5)0.047 (4)0.070 (6)0.006 (4)0.006 (4)−0.004 (4)
C20.058 (5)0.067 (5)0.084 (6)0.004 (4)−0.008 (5)−0.021 (5)
C30.070 (6)0.062 (4)0.076 (6)0.028 (4)0.007 (5)−0.005 (5)
C40.055 (5)0.072 (5)0.086 (6)0.003 (4)0.004 (5)0.000 (5)
C50.069 (6)0.093 (6)0.076 (6)−0.007 (5)−0.012 (4)−0.027 (5)
C60.066 (6)0.077 (5)0.084 (6)0.008 (5)0.000 (5)−0.031 (5)
C70.083 (7)0.128 (7)0.084 (7)0.035 (6)−0.004 (5)0.011 (6)
C80.070 (6)0.058 (5)0.090 (6)0.011 (4)0.010 (5)0.017 (5)
C90.070 (6)0.046 (4)0.062 (5)0.002 (4)0.006 (4)−0.003 (4)
C100.072 (6)0.073 (5)0.074 (6)0.004 (5)0.001 (5)−0.018 (5)
C110.081 (7)0.083 (6)0.093 (7)0.013 (5)0.021 (5)−0.011 (5)
C120.069 (6)0.116 (8)0.083 (7)−0.011 (6)0.019 (6)0.007 (7)
C130.080 (7)0.118 (8)0.095 (8)−0.043 (6)0.002 (6)0.011 (7)
C140.108 (8)0.054 (5)0.090 (7)−0.010 (5)0.015 (5)−0.005 (4)
C150.079 (6)0.069 (5)0.071 (6)0.014 (4)0.003 (5)−0.015 (5)
C160.067 (6)0.061 (4)0.057 (5)0.010 (4)−0.003 (4)−0.001 (4)
C170.087 (7)0.079 (6)0.087 (7)0.017 (5)−0.018 (6)−0.012 (5)
C180.092 (8)0.120 (9)0.104 (9)0.044 (7)−0.011 (6)0.000 (7)
C190.098 (8)0.142 (10)0.081 (8)0.002 (8)−0.028 (6)0.014 (8)
C200.112 (10)0.121 (9)0.104 (9)−0.044 (8)−0.018 (8)0.001 (8)
C210.112 (9)0.073 (6)0.091 (7)−0.010 (5)−0.008 (6)−0.011 (5)
S20.0663 (13)0.0470 (10)0.0872 (16)0.0027 (9)−0.0023 (11)0.0021 (13)
O30.099 (5)0.075 (4)0.123 (5)0.003 (3)−0.005 (4)−0.051 (4)
O40.085 (4)0.080 (4)0.099 (5)0.026 (3)0.004 (4)0.034 (4)
N20.060 (4)0.062 (4)0.047 (4)−0.001 (3)−0.005 (3)0.002 (3)
C220.065 (5)0.054 (4)0.063 (6)0.002 (4)−0.005 (4)0.002 (4)
C230.088 (7)0.062 (5)0.089 (7)−0.006 (5)0.011 (5)0.024 (5)
C240.083 (7)0.090 (6)0.084 (7)−0.009 (5)0.011 (5)0.015 (6)
C250.064 (6)0.093 (6)0.058 (5)0.004 (5)−0.007 (5)−0.007 (5)
C260.079 (7)0.075 (5)0.116 (8)0.017 (5)−0.008 (6)0.020 (6)
C270.080 (7)0.065 (5)0.105 (7)0.010 (5)0.004 (6)0.023 (5)
C280.070 (7)0.165 (11)0.117 (9)0.030 (6)0.000 (6)0.013 (8)
C290.068 (6)0.074 (5)0.077 (6)0.012 (4)−0.008 (5)0.007 (5)
C300.074 (6)0.056 (4)0.049 (5)0.008 (4)−0.004 (4)0.001 (4)
C310.094 (8)0.066 (5)0.081 (6)−0.001 (5)−0.002 (5)0.008 (5)
C320.110 (10)0.112 (8)0.091 (8)−0.029 (7)0.026 (7)−0.003 (6)
C330.077 (7)0.148 (9)0.080 (7)−0.007 (7)0.014 (6)−0.014 (7)
C340.094 (8)0.120 (8)0.095 (8)0.019 (7)0.021 (6)0.008 (7)
C350.086 (7)0.075 (6)0.078 (6)0.021 (5)0.008 (5)0.015 (4)
C360.082 (6)0.057 (4)0.071 (6)0.006 (4)−0.001 (5)−0.014 (4)
C370.077 (6)0.060 (5)0.050 (5)−0.007 (4)−0.003 (4)−0.017 (4)
C380.111 (8)0.053 (5)0.085 (7)−0.012 (5)−0.022 (6)0.007 (4)
C390.084 (8)0.107 (8)0.095 (7)−0.034 (6)0.005 (6)−0.011 (6)
C400.063 (6)0.123 (8)0.109 (8)0.000 (7)−0.005 (6)−0.029 (7)
C410.084 (7)0.086 (6)0.094 (7)0.008 (6)−0.012 (5)−0.010 (6)
C420.084 (6)0.055 (5)0.075 (6)−0.003 (5)−0.009 (5)−0.004 (4)

Geometric parameters (Å, °)

S1—O21.437 (6)S2—O31.415 (6)
S1—O11.438 (6)S2—O41.424 (6)
S1—N11.620 (6)S2—N21.597 (6)
S1—C11.761 (7)S2—C221.770 (7)
N1—C151.463 (9)N2—C291.439 (10)
N1—C81.477 (9)N2—C361.488 (9)
C1—C21.356 (9)C22—C271.370 (10)
C1—C61.371 (10)C22—C231.375 (10)
C2—C31.392 (10)C23—C241.376 (11)
C2—H20.9300C23—H230.9300
C3—C41.326 (11)C24—C251.377 (12)
C3—H30.9300C24—H240.9300
C4—C51.395 (11)C25—C261.373 (12)
C4—C71.539 (11)C25—C281.491 (12)
C5—C61.339 (11)C26—C271.345 (12)
C5—H50.9300C26—H260.9300
C6—H60.9300C27—H270.9300
C7—H7A0.9600C28—H28A0.9600
C7—H7B0.9600C28—H28B0.9600
C7—H7C0.9600C28—H28C0.9600
C8—C91.509 (11)C29—C301.507 (11)
C8—H8A0.9700C29—H29A0.9700
C8—H8B0.9700C29—H29B0.9700
C9—C101.369 (10)C30—C351.379 (10)
C9—C141.385 (10)C30—C311.382 (11)
C10—C111.369 (11)C31—C321.379 (13)
C10—H100.9300C31—H310.9300
C11—C121.339 (13)C32—C331.378 (14)
C11—H110.9300C32—H320.9300
C12—C131.312 (14)C33—C341.371 (14)
C12—H120.9300C33—H330.9300
C13—C141.397 (13)C34—C351.360 (12)
C13—H130.9300C34—H340.9300
C14—H140.9300C35—H350.9300
C15—C161.501 (11)C36—C371.480 (11)
C15—H15A0.9700C36—H36A0.9700
C15—H15B0.9700C36—H36B0.9700
C16—C171.368 (11)C37—C421.373 (10)
C16—C211.370 (11)C37—C381.400 (11)
C17—C181.379 (13)C38—C391.359 (12)
C17—H170.9300C38—H380.9300
C18—C191.313 (14)C39—C401.366 (14)
C18—H180.9300C39—H390.9300
C19—C201.306 (15)C40—C411.363 (13)
C19—H190.9300C40—H400.9300
C20—C211.410 (14)C41—C421.379 (11)
C20—H200.9300C41—H410.9300
C21—H210.9300C42—H420.9300
O2—S1—O1118.5 (3)O3—S2—O4118.3 (4)
O2—S1—N1107.3 (3)O3—S2—N2108.0 (4)
O1—S1—N1108.3 (3)O4—S2—N2107.3 (3)
O2—S1—C1108.9 (3)O3—S2—C22108.2 (4)
O1—S1—C1106.0 (4)O4—S2—C22106.9 (4)
N1—S1—C1107.4 (3)N2—S2—C22107.9 (3)
C15—N1—C8117.7 (6)C29—N2—C36116.6 (6)
C15—N1—S1121.2 (5)C29—N2—S2121.4 (5)
C8—N1—S1117.1 (5)C36—N2—S2118.5 (5)
C2—C1—C6118.8 (7)C27—C22—C23118.7 (7)
C2—C1—S1122.4 (6)C27—C22—S2122.0 (6)
C6—C1—S1118.7 (6)C23—C22—S2119.2 (6)
C1—C2—C3119.2 (7)C22—C23—C24119.0 (8)
C1—C2—H2120.4C22—C23—H23120.5
C3—C2—H2120.4C24—C23—H23120.5
C4—C3—C2121.6 (7)C23—C24—C25122.4 (8)
C4—C3—H3119.2C23—C24—H24118.8
C2—C3—H3119.2C25—C24—H24118.8
C3—C4—C5118.8 (7)C26—C25—C24116.7 (8)
C3—C4—C7121.9 (8)C26—C25—C28121.0 (9)
C5—C4—C7119.1 (8)C24—C25—C28122.2 (9)
C6—C5—C4119.6 (7)C27—C26—C25121.7 (8)
C6—C5—H5120.2C27—C26—H26119.1
C4—C5—H5120.2C25—C26—H26119.1
C5—C6—C1121.8 (7)C26—C27—C22121.3 (8)
C5—C6—H6119.1C26—C27—H27119.3
C1—C6—H6119.1C22—C27—H27119.3
C4—C7—H7A109.5C25—C28—H28A109.5
C4—C7—H7B109.5C25—C28—H28B109.5
H7A—C7—H7B109.5H28A—C28—H28B109.5
C4—C7—H7C109.5C25—C28—H28C109.5
H7A—C7—H7C109.5H28A—C28—H28C109.5
H7B—C7—H7C109.5H28B—C28—H28C109.5
N1—C8—C9112.8 (6)N2—C29—C30114.5 (6)
N1—C8—H8A109.0N2—C29—H29A108.6
C9—C8—H8A109.0C30—C29—H29A108.6
N1—C8—H8B109.0N2—C29—H29B108.6
C9—C8—H8B109.0C30—C29—H29B108.6
H8A—C8—H8B107.8H29A—C29—H29B107.6
C10—C9—C14117.8 (7)C35—C30—C31117.2 (8)
C10—C9—C8120.6 (7)C35—C30—C29121.1 (8)
C14—C9—C8121.5 (7)C31—C30—C29121.6 (7)
C11—C10—C9120.3 (8)C32—C31—C30121.4 (9)
C11—C10—H10119.8C32—C31—H31119.3
C9—C10—H10119.8C30—C31—H31119.3
C12—C11—C10120.3 (9)C33—C32—C31119.6 (10)
C12—C11—H11119.8C33—C32—H32120.2
C10—C11—H11119.8C31—C32—H32120.2
C13—C12—C11122.0 (9)C34—C33—C32119.5 (10)
C13—C12—H12119.0C34—C33—H33120.2
C11—C12—H12119.0C32—C33—H33120.2
C12—C13—C14119.3 (9)C35—C34—C33120.1 (10)
C12—C13—H13120.4C35—C34—H34119.9
C14—C13—H13120.4C33—C34—H34119.9
C9—C14—C13120.2 (8)C34—C35—C30122.1 (9)
C9—C14—H14119.9C34—C35—H35118.9
C13—C14—H14119.9C30—C35—H35118.9
N1—C15—C16113.1 (6)C37—C36—N2112.2 (6)
N1—C15—H15A109.0C37—C36—H36A109.2
C16—C15—H15A109.0N2—C36—H36A109.2
N1—C15—H15B109.0C37—C36—H36B109.2
C16—C15—H15B109.0N2—C36—H36B109.2
H15A—C15—H15B107.8H36A—C36—H36B107.9
C17—C16—C21118.1 (8)C42—C37—C38115.9 (8)
C17—C16—C15122.8 (8)C42—C37—C36122.2 (8)
C21—C16—C15119.0 (8)C38—C37—C36121.9 (8)
C16—C17—C18120.4 (9)C39—C38—C37121.0 (8)
C16—C17—H17119.8C39—C38—H38119.5
C18—C17—H17119.8C37—C38—H38119.5
C19—C18—C17120.5 (10)C38—C39—C40122.2 (9)
C19—C18—H18119.7C38—C39—H39118.9
C17—C18—H18119.7C40—C39—H39118.9
C20—C19—C18121.3 (11)C41—C40—C39117.7 (9)
C20—C19—H19119.3C41—C40—H40121.1
C18—C19—H19119.3C39—C40—H40121.1
C19—C20—C21120.7 (11)C40—C41—C42120.6 (9)
C19—C20—H20119.6C40—C41—H41119.7
C21—C20—H20119.6C42—C41—H41119.7
C16—C21—C20118.8 (9)C37—C42—C41122.4 (8)
C16—C21—H21120.6C37—C42—H42118.8
C20—C21—H21120.6C41—C42—H42118.8
O2—S1—N1—C15−29.7 (6)O3—S2—N2—C2926.3 (6)
O1—S1—N1—C15−158.6 (5)O4—S2—N2—C29154.8 (6)
C1—S1—N1—C1587.3 (6)C22—S2—N2—C29−90.4 (6)
O2—S1—N1—C8173.4 (5)O3—S2—N2—C36−175.9 (5)
O1—S1—N1—C844.5 (6)O4—S2—N2—C36−47.4 (6)
C1—S1—N1—C8−69.6 (6)C22—S2—N2—C3667.4 (6)
O2—S1—C1—C288.0 (7)O3—S2—C22—C27−85.8 (8)
O1—S1—C1—C2−143.5 (7)O4—S2—C22—C27145.8 (7)
N1—S1—C1—C2−27.9 (7)N2—S2—C22—C2730.7 (8)
O2—S1—C1—C6−89.0 (7)O3—S2—C22—C2395.7 (7)
O1—S1—C1—C639.5 (7)O4—S2—C22—C23−32.7 (7)
N1—S1—C1—C6155.1 (6)N2—S2—C22—C23−147.7 (6)
C6—C1—C2—C3−1.2 (12)C27—C22—C23—C243.4 (12)
S1—C1—C2—C3−178.2 (6)S2—C22—C23—C24−178.1 (7)
C1—C2—C3—C44.9 (13)C22—C23—C24—C25−0.7 (14)
C2—C3—C4—C5−5.3 (13)C23—C24—C25—C26−1.9 (14)
C2—C3—C4—C7−179.8 (8)C23—C24—C25—C28−179.9 (9)
C3—C4—C5—C62.1 (14)C24—C25—C26—C271.7 (14)
C7—C4—C5—C6176.8 (8)C28—C25—C26—C27179.8 (10)
C4—C5—C6—C11.5 (14)C25—C26—C27—C221.0 (15)
C2—C1—C6—C5−1.9 (13)C23—C22—C27—C26−3.6 (13)
S1—C1—C6—C5175.2 (7)S2—C22—C27—C26177.9 (8)
C15—N1—C8—C979.6 (8)C36—N2—C29—C3083.2 (8)
S1—N1—C8—C9−122.7 (6)S2—N2—C29—C30−118.6 (6)
N1—C8—C9—C1073.6 (10)N2—C29—C30—C3539.1 (11)
N1—C8—C9—C14−109.7 (8)N2—C29—C30—C31−141.3 (7)
C14—C9—C10—C111.9 (13)C35—C30—C31—C320.0 (13)
C8—C9—C10—C11178.7 (8)C29—C30—C31—C32−179.7 (9)
C9—C10—C11—C12−1.8 (14)C30—C31—C32—C33−1.7 (15)
C10—C11—C12—C132.0 (16)C31—C32—C33—C342.8 (16)
C11—C12—C13—C14−2.2 (16)C32—C33—C34—C35−2.1 (16)
C10—C9—C14—C13−2.2 (12)C33—C34—C35—C300.3 (16)
C8—C9—C14—C13−178.9 (8)C31—C30—C35—C340.7 (13)
C12—C13—C14—C92.3 (15)C29—C30—C35—C34−179.6 (9)
C8—N1—C15—C16−83.4 (8)C29—N2—C36—C37−79.4 (8)
S1—N1—C15—C16119.8 (6)S2—N2—C36—C37121.7 (7)
N1—C15—C16—C17−41.2 (11)N2—C36—C37—C42−69.6 (11)
N1—C15—C16—C21142.3 (8)N2—C36—C37—C38110.8 (8)
C21—C16—C17—C18−2.5 (14)C42—C37—C38—C393.5 (13)
C15—C16—C17—C18−179.1 (9)C36—C37—C38—C39−176.9 (8)
C16—C17—C18—C192.9 (17)C37—C38—C39—C40−2.0 (15)
C17—C18—C19—C20−3.0 (18)C38—C39—C40—C41−0.8 (15)
C18—C19—C20—C212.7 (18)C39—C40—C41—C422.0 (14)
C17—C16—C21—C202.2 (14)C38—C37—C42—C41−2.4 (12)
C15—C16—C21—C20178.9 (8)C36—C37—C42—C41178.0 (8)
C19—C20—C21—C16−2.3 (16)C40—C41—C42—C37−0.3 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8a···O1i0.972.583.456 (9)151
C36—H36a···O4i0.972.513.404 (9)154

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5415).

References

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