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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1017.
Published online 2010 April 2. doi:  10.1107/S1600536810011669
PMCID: PMC2979125

N-(2,3-Dimethyl­phen­yl)-2,4-dimethyl­benzene­sulfonamide

Abstract

The asymmetric unit of the title compound, C16H19NO2S, contains two independent mol­ecules: the dihedral angles between the sulfonyl and anilino benzene rings in the two mol­ecules are 41.5 (1) and 43.8 (1)°. The independent mol­ecules are linked into a dimer by a pair of inter­molecular N—H(...)O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 [triangle]). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009a [triangle],b [triangle],c [triangle]). For related structures, see: Gelbrich et al. (2007 [triangle]); Perlovich et al. (2006 [triangle]).

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Object name is e-66-o1017-scheme1.jpg

Experimental

Crystal data

  • C16H19NO2S
  • M r = 289.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1017-efi1.jpg
  • a = 8.3643 (7) Å
  • b = 10.975 (1) Å
  • c = 16.996 (2) Å
  • α = 83.034 (9)°
  • β = 80.100 (7)°
  • γ = 81.796 (9)°
  • V = 1513.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 299 K
  • 0.34 × 0.30 × 0.20 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.931, T max = 0.958
  • 11164 measured reflections
  • 6136 independent reflections
  • 4196 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.161
  • S = 1.03
  • 6136 reflections
  • 375 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.41 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011669/ci5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011669/ci5070Isup2.hkl

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

supplementary crystallographic information

Comment

As part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a,b,c), in the present work, the structure of 2,4-dimethyl-N-(2,3-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit contains two independent molecules. Both molecules are bent at the N-atoms with C—SO2—NH—C torsion angles of 70.1 (2) and -66.0 (2)°, compared to the values of 53.9 (2)° in 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (II) (Gowda et al., 2009c), 71.0 (2)° in N-(2,3-dimethylphenyl)benzenesulfonamide (III) (Gowda et al., 2009a), and 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (IV) (Gowda et al., 2009b).

The sulfonyl and anilino benzene rings in the two molecules of (I) are tilted relative to each other by 41.5 (1) and 43.8 (1)° in (I), compared to the values of 82.1 (1)° in (II), 64.8 (1)° in (III), and 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of (IV), The remaining bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, pairs of intermolecular N—H···O hydrogen bonds (Table 1) link the independent molecules to form dimers as shown in Fig. 1 and Fig.2.

Experimental

The solution of m-xylene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 273 K. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dimethylbenzenesulfonylchloride was treated with a stoichiometric amount of 2,3-dimethylaniline and boiled for 10 min. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid 2,4-dimethyl-N- (2,3-dimethylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement

H atoms of the NH groups were located in a difference map and their positional parameters were refined [N–H = 0.79 (3)–0.83 (3) Å]. The other H atoms were positioned with idealized geometry using a riding model with C–H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Figures

Fig. 1.
The two independent molecules of (I), showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines.

Crystal data

C16H19NO2SZ = 4
Mr = 289.38F(000) = 616
Triclinic, P1Dx = 1.270 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3643 (7) ÅCell parameters from 3007 reflections
b = 10.975 (1) Åθ = 2.5–28.0°
c = 16.996 (2) ŵ = 0.22 mm1
α = 83.034 (9)°T = 299 K
β = 80.100 (7)°Prism, yellow
γ = 81.796 (9)°0.34 × 0.30 × 0.20 mm
V = 1513.7 (3) Å3

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector6136 independent reflections
Radiation source: fine-focus sealed tube4196 reflections with I > 2σ(I)
graphiteRint = 0.016
Rotation method data acquisition using ω and [var phi] scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −10→10
Tmin = 0.931, Tmax = 0.958k = −13→13
11164 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0699P)2 + 0.9151P] where P = (Fo2 + 2Fc2)/3
6136 reflections(Δ/σ)max = 0.002
375 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.41 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 (Å2)

xyzUiso*/Ueq
C10.7579 (3)0.1917 (2)0.30498 (15)0.0439 (6)
C20.8079 (3)0.0826 (2)0.35144 (17)0.0487 (6)
C30.6896 (4)0.0046 (3)0.38031 (18)0.0559 (7)
H30.7200−0.06850.41100.067*
C40.5295 (4)0.0283 (3)0.36652 (18)0.0548 (7)
C50.4848 (4)0.1366 (3)0.32071 (19)0.0582 (8)
H50.37810.15500.31010.070*
C60.5965 (3)0.2167 (3)0.29087 (18)0.0532 (7)
H60.56420.28950.26050.064*
C70.9403 (3)0.3704 (2)0.40309 (15)0.0405 (6)
C81.1020 (3)0.3881 (2)0.40397 (16)0.0431 (6)
C91.1659 (4)0.3549 (3)0.47568 (18)0.0532 (7)
C101.0649 (5)0.3099 (3)0.54282 (18)0.0649 (9)
H101.10670.28880.59060.078*
C110.9048 (5)0.2950 (3)0.54161 (19)0.0664 (9)
H110.83970.26520.58800.080*
C120.8422 (4)0.3247 (3)0.47111 (18)0.0545 (7)
H120.73460.31420.46920.065*
C130.9783 (4)0.0452 (3)0.3710 (2)0.0703 (9)
H13A1.01480.11360.39020.084*
H13B1.05100.02200.32350.084*
H13C0.9778−0.02360.41160.084*
C140.4087 (4)−0.0607 (3)0.4010 (2)0.0770 (10)
H14A0.4628−0.13130.42930.092*
H14B0.3640−0.08690.35840.092*
H14C0.3221−0.02060.43740.092*
C151.2017 (4)0.4467 (3)0.33078 (19)0.0594 (8)
H15A1.12990.49700.29800.071*
H15B1.26620.38330.30070.071*
H15C1.27250.49730.34690.071*
C161.3387 (4)0.3701 (4)0.4809 (2)0.0815 (11)
H16A1.35840.45340.46160.098*
H16B1.41230.31360.44860.098*
H16C1.35630.35310.53570.098*
N10.8735 (3)0.4042 (2)0.32974 (14)0.0487 (6)
H1N0.783 (4)0.447 (3)0.3348 (18)0.058*
O10.8196 (3)0.37379 (19)0.19753 (12)0.0638 (6)
O21.0524 (2)0.24770 (19)0.25134 (12)0.0596 (5)
S10.88758 (9)0.30509 (6)0.26408 (4)0.0484 (2)
C170.6666 (3)0.7822 (2)0.21219 (16)0.0459 (6)
C180.6232 (3)0.8894 (2)0.16309 (18)0.0503 (7)
C190.7455 (4)0.9638 (3)0.1334 (2)0.0621 (8)
H190.71991.03520.10020.075*
C200.9028 (4)0.9375 (3)0.1505 (2)0.0621 (8)
C210.9409 (4)0.8305 (3)0.1997 (2)0.0644 (9)
H211.04610.81070.21220.077*
C220.8243 (4)0.7539 (3)0.22987 (18)0.0552 (7)
H220.85120.68210.26250.066*
C230.4896 (3)0.6176 (2)0.10779 (15)0.0403 (6)
C240.6025 (3)0.6394 (2)0.03794 (16)0.0427 (6)
C250.5393 (4)0.6793 (2)−0.03382 (17)0.0523 (7)
C260.3736 (4)0.6952 (3)−0.0335 (2)0.0615 (8)
H260.33370.7213−0.08130.074*
C270.2650 (4)0.6736 (3)0.0354 (2)0.0628 (8)
H270.15310.68620.03420.075*
C280.3231 (3)0.6332 (3)0.10660 (18)0.0526 (7)
H280.25060.61660.15340.063*
C290.4565 (4)0.9307 (3)0.1406 (2)0.0710 (10)
H29A0.38030.95030.18780.085*
H29B0.42190.86560.11720.085*
H29C0.46091.00280.10260.085*
C301.0290 (5)1.0232 (4)0.1153 (3)0.0918 (12)
H30A1.07681.04700.15770.110*
H30B0.97751.09550.08750.110*
H30C1.11280.98130.07840.110*
C310.7824 (3)0.6221 (3)0.03934 (18)0.0588 (8)
H31A0.80490.57290.08780.071*
H31B0.81970.70140.03730.071*
H31C0.83820.5810−0.00620.071*
C320.6546 (5)0.7030 (3)−0.11119 (19)0.0778 (10)
H32A0.72130.6273−0.12430.093*
H32B0.72320.7631−0.10490.093*
H32C0.59250.7337−0.15360.093*
N20.5434 (3)0.5754 (2)0.18338 (14)0.0469 (5)
H2N0.627 (4)0.532 (3)0.1814 (18)0.056*
O30.5930 (3)0.59831 (19)0.31781 (12)0.0651 (6)
O40.3674 (2)0.73252 (18)0.26308 (12)0.0575 (5)
S20.53042 (9)0.67152 (6)0.25099 (4)0.0487 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0468 (15)0.0455 (14)0.0409 (15)0.0010 (11)−0.0121 (11)−0.0104 (12)
C20.0506 (16)0.0447 (14)0.0516 (16)0.0046 (12)−0.0169 (13)−0.0076 (12)
C30.0653 (19)0.0428 (15)0.0594 (19)−0.0036 (13)−0.0149 (15)−0.0011 (13)
C40.0581 (18)0.0546 (16)0.0546 (18)−0.0077 (14)−0.0093 (14)−0.0154 (14)
C50.0461 (16)0.0651 (18)0.066 (2)−0.0035 (14)−0.0159 (14)−0.0128 (16)
C60.0520 (16)0.0534 (16)0.0555 (18)0.0040 (13)−0.0212 (13)−0.0045 (13)
C70.0483 (15)0.0314 (12)0.0427 (14)−0.0057 (10)−0.0086 (11)−0.0037 (10)
C80.0499 (15)0.0370 (13)0.0423 (15)−0.0060 (11)−0.0057 (11)−0.0051 (11)
C90.0568 (17)0.0502 (15)0.0555 (18)0.0025 (13)−0.0174 (14)−0.0156 (14)
C100.100 (3)0.0516 (17)0.0416 (17)0.0086 (17)−0.0207 (17)−0.0049 (14)
C110.096 (3)0.0519 (17)0.0432 (18)−0.0120 (17)0.0093 (16)0.0029 (14)
C120.0590 (18)0.0488 (15)0.0526 (18)−0.0138 (13)0.0055 (13)−0.0047 (13)
C130.061 (2)0.0565 (18)0.094 (3)0.0012 (15)−0.0319 (18)0.0124 (17)
C140.073 (2)0.077 (2)0.086 (3)−0.0253 (18)−0.0081 (19)−0.010 (2)
C150.0515 (17)0.0656 (18)0.0616 (19)−0.0195 (14)−0.0001 (14)−0.0060 (15)
C160.065 (2)0.099 (3)0.089 (3)0.0086 (19)−0.0332 (19)−0.036 (2)
N10.0485 (13)0.0439 (12)0.0538 (14)0.0008 (10)−0.0144 (11)−0.0041 (11)
O10.0778 (14)0.0661 (13)0.0476 (12)−0.0039 (11)−0.0223 (10)0.0064 (10)
O20.0529 (12)0.0671 (13)0.0570 (13)−0.0047 (10)−0.0030 (9)−0.0103 (10)
S10.0531 (4)0.0499 (4)0.0421 (4)−0.0027 (3)−0.0118 (3)−0.0021 (3)
C170.0507 (16)0.0436 (14)0.0448 (15)−0.0017 (12)−0.0113 (12)−0.0093 (12)
C180.0495 (16)0.0418 (14)0.0612 (18)−0.0015 (12)−0.0141 (13)−0.0090 (13)
C190.064 (2)0.0461 (16)0.078 (2)−0.0048 (14)−0.0169 (16)−0.0052 (15)
C200.0514 (18)0.0637 (19)0.075 (2)−0.0111 (14)−0.0056 (15)−0.0245 (17)
C210.0495 (17)0.074 (2)0.075 (2)0.0061 (15)−0.0213 (16)−0.0271 (18)
C220.0545 (17)0.0564 (17)0.0567 (18)0.0027 (14)−0.0185 (14)−0.0110 (14)
C230.0491 (15)0.0332 (12)0.0379 (14)−0.0036 (10)−0.0058 (11)−0.0042 (10)
C240.0499 (15)0.0365 (12)0.0429 (15)−0.0088 (11)−0.0066 (11)−0.0058 (11)
C250.073 (2)0.0433 (14)0.0434 (16)−0.0117 (13)−0.0124 (14)−0.0041 (12)
C260.080 (2)0.0523 (17)0.058 (2)−0.0022 (15)−0.0328 (17)−0.0041 (14)
C270.0535 (18)0.0624 (19)0.079 (2)−0.0035 (14)−0.0242 (17)−0.0161 (17)
C280.0459 (16)0.0538 (16)0.0580 (18)−0.0101 (12)−0.0029 (13)−0.0086 (14)
C290.0588 (19)0.0538 (18)0.100 (3)−0.0028 (15)−0.0298 (18)0.0126 (18)
C300.067 (2)0.090 (3)0.124 (4)−0.025 (2)−0.008 (2)−0.024 (2)
C310.0499 (17)0.0703 (19)0.0556 (18)−0.0144 (14)0.0005 (13)−0.0076 (15)
C320.109 (3)0.077 (2)0.0454 (19)−0.022 (2)−0.0035 (18)0.0044 (17)
N20.0525 (14)0.0437 (12)0.0413 (13)−0.0003 (10)−0.0061 (11)−0.0001 (10)
O30.0854 (15)0.0675 (13)0.0381 (11)0.0013 (11)−0.0128 (10)0.0030 (10)
O40.0536 (12)0.0617 (12)0.0523 (12)−0.0006 (9)0.0027 (9)−0.0089 (10)
S20.0574 (4)0.0501 (4)0.0362 (4)−0.0020 (3)−0.0062 (3)−0.0025 (3)

Geometric parameters (Å, °)

C1—C61.395 (4)C17—C221.386 (4)
C1—C21.405 (4)C17—C181.399 (4)
C1—S11.768 (3)C17—S21.775 (3)
C2—C31.387 (4)C18—C191.389 (4)
C2—C131.508 (4)C18—C291.501 (4)
C3—C41.382 (4)C19—C201.379 (4)
C3—H30.93C19—H190.93
C4—C51.381 (4)C20—C211.388 (4)
C4—C141.502 (4)C20—C301.512 (5)
C5—C61.366 (4)C21—C221.371 (4)
C5—H50.93C21—H210.93
C6—H60.93C22—H220.93
C7—C121.383 (4)C23—C281.382 (4)
C7—C81.397 (3)C23—C241.403 (4)
C7—N11.440 (3)C23—N21.437 (3)
C8—C91.402 (4)C24—C251.409 (4)
C8—C151.503 (4)C24—C311.493 (4)
C9—C101.382 (4)C25—C261.372 (4)
C9—C161.497 (4)C25—C321.509 (4)
C10—C111.376 (5)C26—C271.371 (5)
C10—H100.93C26—H260.93
C11—C121.374 (4)C27—C281.381 (4)
C11—H110.93C27—H270.93
C12—H120.93C28—H280.93
C13—H13A0.96C29—H29A0.96
C13—H13B0.96C29—H29B0.96
C13—H13C0.96C29—H29C0.96
C14—H14A0.96C30—H30A0.96
C14—H14B0.96C30—H30B0.96
C14—H14C0.96C30—H30C0.96
C15—H15A0.96C31—H31A0.96
C15—H15B0.96C31—H31B0.96
C15—H15C0.96C31—H31C0.96
C16—H16A0.96C32—H32A0.96
C16—H16B0.96C32—H32B0.96
C16—H16C0.96C32—H32C0.96
N1—S11.630 (2)N2—S21.632 (2)
N1—H1N0.83 (3)N2—H2N0.79 (3)
O1—S11.436 (2)O3—S21.439 (2)
O2—S11.424 (2)O4—S21.423 (2)
C6—C1—C2119.8 (3)C22—C17—C18120.8 (3)
C6—C1—S1116.4 (2)C22—C17—S2116.1 (2)
C2—C1—S1123.8 (2)C18—C17—S2123.0 (2)
C3—C2—C1116.4 (2)C19—C18—C17116.6 (3)
C3—C2—C13118.8 (3)C19—C18—C29117.8 (3)
C1—C2—C13124.8 (3)C17—C18—C29125.7 (3)
C4—C3—C2124.3 (3)C20—C19—C18123.6 (3)
C4—C3—H3117.9C20—C19—H19118.2
C2—C3—H3117.9C18—C19—H19118.2
C5—C4—C3117.7 (3)C19—C20—C21118.1 (3)
C5—C4—C14121.5 (3)C19—C20—C30120.2 (3)
C3—C4—C14120.8 (3)C21—C20—C30121.7 (3)
C6—C5—C4120.3 (3)C22—C21—C20120.3 (3)
C6—C5—H5119.8C22—C21—H21119.8
C4—C5—H5119.8C20—C21—H21119.8
C5—C6—C1121.5 (3)C21—C22—C17120.7 (3)
C5—C6—H6119.3C21—C22—H22119.7
C1—C6—H6119.3C17—C22—H22119.7
C12—C7—C8121.8 (3)C28—C23—C24121.7 (2)
C12—C7—N1119.5 (2)C28—C23—N2117.3 (2)
C8—C7—N1118.7 (2)C24—C23—N2120.9 (2)
C7—C8—C9118.3 (2)C23—C24—C25117.3 (2)
C7—C8—C15120.5 (2)C23—C24—C31121.6 (2)
C9—C8—C15121.1 (3)C25—C24—C31121.1 (3)
C10—C9—C8118.7 (3)C26—C25—C24120.0 (3)
C10—C9—C16120.1 (3)C26—C25—C32120.1 (3)
C8—C9—C16121.2 (3)C24—C25—C32119.8 (3)
C11—C10—C9122.5 (3)C25—C26—C27121.9 (3)
C11—C10—H10118.8C25—C26—H26119.1
C9—C10—H10118.8C27—C26—H26119.1
C12—C11—C10119.2 (3)C26—C27—C28119.5 (3)
C12—C11—H11120.4C26—C27—H27120.2
C10—C11—H11120.4C28—C27—H27120.2
C11—C12—C7119.5 (3)C27—C28—C23119.6 (3)
C11—C12—H12120.2C27—C28—H28120.2
C7—C12—H12120.2C23—C28—H28120.2
C2—C13—H13A109.5C18—C29—H29A109.5
C2—C13—H13B109.5C18—C29—H29B109.5
H13A—C13—H13B109.5H29A—C29—H29B109.5
C2—C13—H13C109.5C18—C29—H29C109.5
H13A—C13—H13C109.5H29A—C29—H29C109.5
H13B—C13—H13C109.5H29B—C29—H29C109.5
C4—C14—H14A109.5C20—C30—H30A109.5
C4—C14—H14B109.5C20—C30—H30B109.5
H14A—C14—H14B109.5H30A—C30—H30B109.5
C4—C14—H14C109.5C20—C30—H30C109.5
H14A—C14—H14C109.5H30A—C30—H30C109.5
H14B—C14—H14C109.5H30B—C30—H30C109.5
C8—C15—H15A109.5C24—C31—H31A109.5
C8—C15—H15B109.5C24—C31—H31B109.5
H15A—C15—H15B109.5H31A—C31—H31B109.5
C8—C15—H15C109.5C24—C31—H31C109.5
H15A—C15—H15C109.5H31A—C31—H31C109.5
H15B—C15—H15C109.5H31B—C31—H31C109.5
C9—C16—H16A109.5C25—C32—H32A109.5
C9—C16—H16B109.5C25—C32—H32B109.5
H16A—C16—H16B109.5H32A—C32—H32B109.5
C9—C16—H16C109.5C25—C32—H32C109.5
H16A—C16—H16C109.5H32A—C32—H32C109.5
H16B—C16—H16C109.5H32B—C32—H32C109.5
C7—N1—S1121.05 (17)C23—N2—S2120.16 (17)
C7—N1—H1N115 (2)C23—N2—H2N116 (2)
S1—N1—H1N112 (2)S2—N2—H2N110 (2)
O2—S1—O1119.10 (13)O4—S2—O3118.80 (13)
O2—S1—N1107.81 (12)O4—S2—N2108.11 (12)
O1—S1—N1105.08 (12)O3—S2—N2104.97 (12)
O2—S1—C1109.11 (12)O4—S2—C17109.21 (12)
O1—S1—C1107.12 (13)O3—S2—C17107.64 (13)
N1—S1—C1108.16 (12)N2—S2—C17107.58 (12)
C6—C1—C2—C30.5 (4)C22—C17—C18—C190.3 (4)
S1—C1—C2—C3178.7 (2)S2—C17—C18—C19−176.3 (2)
C6—C1—C2—C13−179.9 (3)C22—C17—C18—C29−179.1 (3)
S1—C1—C2—C13−1.8 (4)S2—C17—C18—C294.2 (4)
C1—C2—C3—C4−0.4 (4)C17—C18—C19—C20−0.6 (5)
C13—C2—C3—C4−180.0 (3)C29—C18—C19—C20178.9 (3)
C2—C3—C4—C50.3 (4)C18—C19—C20—C210.3 (5)
C2—C3—C4—C14−179.2 (3)C18—C19—C20—C30179.7 (3)
C3—C4—C5—C6−0.3 (4)C19—C20—C21—C220.1 (5)
C14—C4—C5—C6179.2 (3)C30—C20—C21—C22−179.2 (3)
C4—C5—C6—C10.5 (4)C20—C21—C22—C17−0.4 (5)
C2—C1—C6—C5−0.6 (4)C18—C17—C22—C210.1 (4)
S1—C1—C6—C5−178.9 (2)S2—C17—C22—C21177.0 (2)
C12—C7—C8—C91.9 (4)C28—C23—C24—C250.6 (4)
N1—C7—C8—C9180.0 (2)N2—C23—C24—C25179.3 (2)
C12—C7—C8—C15−175.4 (2)C28—C23—C24—C31−179.8 (2)
N1—C7—C8—C152.7 (4)N2—C23—C24—C31−1.2 (4)
C7—C8—C9—C10−2.0 (4)C23—C24—C25—C26−0.1 (4)
C15—C8—C9—C10175.2 (3)C31—C24—C25—C26−179.6 (3)
C7—C8—C9—C16179.4 (3)C23—C24—C25—C32−179.3 (3)
C15—C8—C9—C16−3.4 (4)C31—C24—C25—C321.1 (4)
C8—C9—C10—C110.9 (4)C24—C25—C26—C270.2 (4)
C16—C9—C10—C11179.4 (3)C32—C25—C26—C27179.5 (3)
C9—C10—C11—C120.6 (5)C25—C26—C27—C28−0.9 (5)
C10—C11—C12—C7−0.8 (4)C26—C27—C28—C231.4 (4)
C8—C7—C12—C11−0.4 (4)C24—C23—C28—C27−1.3 (4)
N1—C7—C12—C11−178.5 (2)N2—C23—C28—C27180.0 (2)
C12—C7—N1—S1−91.8 (3)C28—C23—N2—S2−77.9 (3)
C8—C7—N1—S190.0 (3)C24—C23—N2—S2103.4 (2)
C7—N1—S1—O2−47.8 (2)C23—N2—S2—O451.8 (2)
C7—N1—S1—O1−175.8 (2)C23—N2—S2—O3179.5 (2)
C7—N1—S1—C170.1 (2)C23—N2—S2—C17−66.0 (2)
C6—C1—S1—O2−154.2 (2)C22—C17—S2—O4152.1 (2)
C2—C1—S1—O227.5 (3)C18—C17—S2—O4−31.1 (3)
C6—C1—S1—O1−24.0 (2)C22—C17—S2—O321.9 (2)
C2—C1—S1—O1157.7 (2)C18—C17—S2—O3−161.3 (2)
C6—C1—S1—N188.8 (2)C22—C17—S2—N2−90.8 (2)
C2—C1—S1—N1−89.5 (2)C18—C17—S2—N286.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.83 (3)2.15 (3)2.952 (3)161 (3)
N2—H2N···O10.79 (3)2.22 (3)2.982 (3)164 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5070).

References

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