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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o190.
Published online 2009 December 19. doi:  10.1107/S1600536809053707
PMCID: PMC2980117

2,4-Dichloro-N-(4-methyl­phen­yl)benzene­sulfonamide

Abstract

The title compound, C13H11Cl2NO2S, crystallizes with four independent mol­ecules in the asymmetric unit. In each of the four mol­ecules, the conformation of the N—C bond in the C—SO2—NH—C segment is gauche with respect to both S=O bonds. The mol­ecules are twisted at the S—N bonds with C—SO2—NH—C torsion angles of 60.6 (4), −59.7 (3), 63.9 (4) and 53.0 (4)°. The benzene rings in two of the mol­ecules are disordered with multiple positions resolved in each case. The crystal structure features inversion dimers linked by pairs of N—H(...)O hydrogen bonds for each of the four molecules.

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]). For related structures, see: Gelbrich et al. (2007 [triangle]); Perlovich et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o190-scheme1.jpg

Experimental

Crystal data

  • C13H11Cl2NO2S
  • M r = 316.19
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o190-efi1.jpg
  • a = 11.760 (2) Å
  • b = 14.875 (2) Å
  • c = 16.672 (3) Å
  • α = 85.06 (1)°
  • β = 75.26 (1)°
  • γ = 87.20 (1)°
  • V = 2808.9 (8) Å3
  • Z = 8
  • Cu Kα radiation
  • μ = 5.53 mm−1
  • T = 299 K
  • 0.50 × 0.35 × 0.30 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.169, T max = 0.288
  • 10777 measured reflections
  • 9992 independent reflections
  • 7795 reflections with I > 2σ(I)
  • R int = 0.016
  • 3 standard reflections every 3 min
  • intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.199
  • S = 1.05
  • 9992 reflections
  • 802 parameters
  • 18 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.70 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); 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/S1600536809053707/tk2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053707/tk2592Isup2.hkl

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

supplementary crystallographic information

Comment

In the present work, as part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a, b), the structure of 2,4-dichloro-N-(4-methylphenyl)benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains four independent molecules. The conformations of the N—C bonds in the C—SO2—NH—C segment have gauche torsions with respect to the S═O bonds (Fig. 1). The molecules are twisted at the S–N bonds with the C—SO2—NH—C torsion angles being 60.6 (4)°, -59.7 (3)°, 63.9 (4)°, and 53.0 (4)°, respectively, compared to the values of -48.2 (2)° in 2,4-dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide (II) (Gowda et al., 2009b) and -69.7 (2)° in 2,4-dimethyl-N-(3,4-dichlorophenyl)benzenesulfonamide (III) (Gowda et al., 2009a).

The sulfonyl benzene and the aniline benzene rings in the four molecules of (I) are tilted relative to each other by 85.2 (1)° (molecule 1), 80.5 (2)° (molecule 2, disordered orientation A), 80.1 (2)° (molecule 2, orientation B), 87.5 (7) (molecule 3, disordered orientation A), 87.0 (6)° (molecule 3, orientation B) and 72.4 (1)° (molecule 4), compared to the values of 68.9 (1)° in (II) and 82.4 (1)° in (III). The other bond parameters in (I) are similar to those observed in (II), (III) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds link the molecules through inversion-related dimers, Fig. 2 and Table 1.

Experimental

The solution of 1,3-dichlorobenzene (10 ml) in chloroform (40 ml) was treated drop-wise 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-dichlorobenzenesulfonylchloride was treated with a stoichiometric amount of p-toluidine and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid 2,4-dichloro-N-(4-methylphenyl)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

The H atoms of the NH groups were located in a difference map and refined with the distance restraint N—H = 0.86 (3) Å. The other H atoms were positioned with idealized geometry using a riding model [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).

Two of the benzene rings with C21, C22, C24, C25 and C28, C29, C30, C31, C32, respectively, with Cl5 and Cl6 are disordered and were refined using a split model. The corresponding site-occupation factors were fixed to 0.50:0.50, and their corresponding bond distances in the disordered groups were restrained to be equal.

Figures

Fig. 1.
Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level. Both disorder components are shown. The disorder components are shown with dashed bonds.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines. For more clarity the disorder components were omitted.

Crystal data

C13H11Cl2NO2SZ = 8
Mr = 316.19F(000) = 1296
Triclinic, P1Dx = 1.495 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 11.760 (2) ÅCell parameters from 25 reflections
b = 14.875 (2) Åθ = 5.3–17.4°
c = 16.672 (3) ŵ = 5.53 mm1
α = 85.06 (1)°T = 299 K
β = 75.26 (1)°Rod, colourless
γ = 87.20 (1)°0.50 × 0.35 × 0.30 mm
V = 2808.9 (8) Å3

Data collection

Enraf–Nonius CAD-4 diffractometer7795 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 67.0°, θmin = 2.8°
ω/2θ scansh = −14→13
Absorption correction: ψ scan (North et al., 1968)k = −17→17
Tmin = 0.169, Tmax = 0.288l = −19→1
10777 measured reflections3 standard reflections every 120 min
9992 independent reflections intensity decay: 1.0%

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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.199w = 1/[σ2(Fo2) + (0.1384P)2 + 0.7496P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.003
9992 reflectionsΔρmax = 0.70 e Å3
802 parametersΔρmin = −0.67 e Å3
18 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (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.
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*/UeqOcc. (<1)
Cl1−0.08874 (12)0.59478 (9)0.63447 (7)0.0872 (4)
Cl2−0.12670 (14)0.54619 (13)0.95925 (8)0.1092 (5)
S10.07830 (8)0.41228 (7)0.60370 (6)0.0560 (2)
O10.1536 (3)0.33756 (19)0.61595 (18)0.0668 (7)
O2−0.0180 (3)0.3988 (2)0.56828 (18)0.0674 (7)
N10.1532 (3)0.4898 (3)0.5437 (2)0.0609 (8)
H1N0.108 (4)0.518 (3)0.519 (3)0.073*
C10.0217 (3)0.4545 (3)0.7027 (2)0.0545 (8)
C2−0.0507 (3)0.5305 (3)0.7158 (2)0.0592 (9)
C3−0.0953 (4)0.5585 (3)0.7950 (3)0.0694 (11)
H3−0.14330.61010.80300.083*
C4−0.0686 (4)0.5099 (4)0.8609 (3)0.0725 (12)
C50.0029 (4)0.4340 (4)0.8506 (3)0.0771 (13)
H50.02160.40160.89600.092*
C60.0466 (4)0.4068 (3)0.7712 (3)0.0680 (10)
H60.09410.35480.76370.082*
C70.2553 (3)0.5316 (2)0.5541 (2)0.0532 (8)
C80.2770 (4)0.6176 (3)0.5178 (3)0.0695 (11)
H80.22450.64710.49040.083*
C90.3769 (5)0.6602 (3)0.5220 (3)0.0752 (12)
H90.39130.71820.49680.090*
C100.4551 (4)0.6186 (3)0.5628 (2)0.0625 (10)
C110.4318 (4)0.5330 (3)0.5987 (2)0.0612 (9)
H110.48400.50360.62650.073*
C120.3323 (3)0.4890 (3)0.5948 (2)0.0592 (9)
H120.31810.43090.61970.071*
C130.5661 (5)0.6658 (4)0.5654 (4)0.0893 (15)
H13A0.54720.72780.57640.107*
H13B0.62290.66300.51290.107*
H13C0.59830.63630.60870.107*
Cl30.46567 (10)0.32311 (8)−0.01888 (6)0.0732 (3)
Cl40.22211 (10)0.06126 (7)0.17786 (7)0.0745 (3)
S20.44663 (7)0.43952 (6)0.14212 (6)0.0506 (2)
O30.3878 (2)0.49470 (18)0.09004 (18)0.0640 (7)
O40.4332 (2)0.46087 (18)0.22529 (17)0.0633 (7)
N20.5839 (3)0.4397 (2)0.09413 (19)0.0511 (7)
H2N0.599 (4)0.452 (3)0.0419 (17)0.061*
C140.3966 (3)0.3273 (2)0.1493 (2)0.0471 (7)
C150.3988 (3)0.2804 (2)0.0807 (2)0.0520 (8)
C160.3475 (3)0.1974 (3)0.0899 (2)0.0573 (9)
H160.35020.16580.04360.069*
C170.2922 (3)0.1620 (2)0.1688 (2)0.0545 (8)
C180.2910 (3)0.2054 (3)0.2379 (2)0.0575 (9)
H180.25520.18000.29070.069*
C190.3442 (3)0.2883 (3)0.2278 (2)0.0527 (8)
H190.34480.31820.27440.063*
C200.6714 (3)0.3869 (2)0.1234 (2)0.0479 (7)
C21A0.7603 (11)0.3477 (10)0.0654 (9)0.077 (4)0.50
H21A0.76140.35330.00920.092*0.50
C22A0.8484 (13)0.2994 (10)0.0937 (8)0.082 (4)0.50
H22A0.90920.27320.05470.099*0.50
C230.8512 (4)0.2881 (3)0.1755 (3)0.0635 (10)
C24A0.7924 (11)0.3567 (9)0.2204 (10)0.070 (5)0.50
H24A0.81140.37010.26890.084*0.50
C25A0.7054 (12)0.4056 (10)0.1935 (11)0.070 (4)0.50
H25A0.66780.45310.22360.084*0.50
C260.9501 (5)0.2362 (3)0.2036 (4)0.0882 (15)
H26A1.01690.23120.15700.106*
H26B0.92450.17690.22630.106*
H26C0.97150.26740.24540.106*
Cl5A0.5808 (14)0.1138 (12)0.3444 (10)0.103 (4)0.50
Cl6A0.6252 (9)0.0856 (5)0.0323 (5)0.101 (2)0.50
S30.43046 (9)−0.07138 (7)0.40080 (6)0.0597 (3)
O50.5301 (3)−0.0893 (2)0.43401 (17)0.0743 (8)
O60.3574 (3)−0.14399 (19)0.3980 (2)0.0750 (8)
N30.3536 (3)0.0045 (2)0.45511 (19)0.0612 (8)
H3N0.387 (4)0.027 (3)0.485 (3)0.073*
C270.4811 (4)−0.0252 (3)0.2966 (2)0.0573 (9)
C28A0.546 (2)0.0477 (16)0.2742 (6)0.072 (9)0.50
C29A0.6004 (18)0.0809 (14)0.1929 (9)0.087 (9)0.50
H29A0.65760.12450.18060.105*0.50
C30A0.5608 (19)0.0425 (15)0.1328 (10)0.079 (6)0.50
C31A0.503 (3)−0.036 (2)0.1623 (14)0.089 (8)0.50
H31A0.5071−0.07600.12150.106*0.50
C32A0.4397 (12)−0.0679 (15)0.2396 (12)0.064 (4)0.50
H32A0.3806−0.11000.25140.077*0.50
C330.2459 (3)0.0463 (3)0.4465 (2)0.0556 (9)
C340.1758 (4)0.0130 (3)0.4031 (2)0.0619 (9)
H340.1994−0.03870.37480.074*
C350.0693 (4)0.0561 (3)0.4009 (3)0.0668 (10)
H350.02250.03260.37090.080*
C360.0308 (4)0.1329 (3)0.4420 (3)0.0663 (11)
C370.1042 (4)0.1656 (3)0.4840 (3)0.0754 (12)
H370.08120.21780.51150.090*
C380.2099 (4)0.1246 (3)0.4870 (3)0.0698 (11)
H380.25740.14900.51600.084*
C39−0.0857 (5)0.1768 (4)0.4424 (4)0.0963 (17)
H39A−0.14650.13390.46420.116*
H39B−0.08740.19800.38660.116*
H39C−0.09860.22690.47660.116*
Cl70.40993 (13)0.36517 (9)0.77244 (10)0.0987 (5)
Cl80.11054 (11)0.15622 (9)0.99354 (7)0.0817 (4)
S40.09578 (9)0.02646 (6)0.85004 (7)0.0648 (3)
O70.1111 (3)−0.0097 (2)0.7718 (2)0.0848 (10)
O80.1202 (3)−0.0299 (2)0.9177 (2)0.0829 (10)
N4−0.0385 (3)0.0638 (2)0.8824 (2)0.0614 (8)
H4N−0.059 (4)0.057 (3)0.9359 (17)0.074*
C400.1842 (3)0.1232 (2)0.8301 (2)0.0529 (8)
C410.1893 (3)0.1785 (3)0.8918 (2)0.0538 (8)
C420.2583 (3)0.2528 (3)0.8738 (3)0.0597 (9)
H420.26220.28930.91550.072*
C430.3211 (3)0.2724 (3)0.7939 (3)0.0610 (10)
C440.3171 (3)0.2202 (3)0.7304 (3)0.0629 (10)
H440.36000.23480.67610.076*
C450.2471 (3)0.1451 (3)0.7498 (3)0.0595 (9)
H450.24270.10890.70800.071*
C46−0.0905 (3)0.1327 (3)0.8388 (3)0.0568 (9)
C47−0.0740 (4)0.1382 (3)0.7535 (3)0.0723 (11)
H47−0.02440.09680.72150.087*
C48−0.1319 (4)0.2055 (3)0.7165 (3)0.0726 (11)
H48−0.11880.20890.65900.087*
C49−0.2076 (4)0.2678 (3)0.7594 (3)0.0654 (10)
C50−0.2229 (4)0.2607 (4)0.8440 (3)0.0838 (14)
H50−0.27440.30140.87550.101*
C51−0.1645 (4)0.1951 (4)0.8846 (3)0.0757 (12)
H51−0.17520.19340.94200.091*
C52−0.2700 (5)0.3396 (4)0.7162 (4)0.0911 (15)
H52A−0.31740.31170.68670.109*
H52B−0.21310.37670.67760.109*
H52C−0.31930.37630.75660.109*
C21B0.7292 (11)0.3161 (7)0.0817 (8)0.062 (3)0.50
H21B0.70960.30160.03380.075*0.50
C22B0.8162 (13)0.2652 (8)0.1088 (8)0.067 (3)0.50
H22B0.85060.21510.08120.081*0.50
C24B0.7599 (11)0.3289 (10)0.2294 (10)0.073 (4)0.50
H24B0.75810.32210.28570.088*0.50
C25B0.6708 (13)0.3790 (11)0.2065 (11)0.071 (4)0.50
H25B0.61190.40670.24570.085*0.50
C28B0.555 (2)0.0503 (14)0.2758 (7)0.065 (8)0.50
C29B0.5912 (15)0.0761 (14)0.1903 (7)0.079 (7)0.50
H29B0.62370.13230.17200.095*0.50
C30B0.5777 (16)0.0172 (13)0.1333 (8)0.069 (5)0.50
C31B0.501 (3)−0.0529 (19)0.1478 (12)0.065 (4)0.50
H31B0.4743−0.07970.10800.078*0.50
C32B0.4721 (12)−0.0758 (14)0.2320 (9)0.052 (3)0.50
H32B0.4422−0.13320.24810.063*0.50
Cl5B0.5918 (13)0.1076 (12)0.3506 (10)0.091 (3)0.50
Cl6B0.6282 (9)0.0443 (5)0.0266 (5)0.101 (2)0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0967 (8)0.0930 (8)0.0642 (6)0.0389 (7)−0.0163 (6)0.0017 (6)
Cl20.0935 (9)0.1752 (16)0.0638 (7)0.0248 (10)−0.0226 (6)−0.0444 (8)
S10.0539 (5)0.0632 (5)0.0508 (5)0.0033 (4)−0.0129 (4)−0.0071 (4)
O10.0687 (17)0.0607 (16)0.0695 (17)0.0104 (13)−0.0153 (14)−0.0095 (13)
O20.0606 (16)0.0834 (19)0.0607 (16)−0.0066 (14)−0.0182 (13)−0.0087 (14)
N10.0495 (17)0.079 (2)0.0542 (18)0.0019 (15)−0.0143 (14)−0.0013 (16)
C10.0480 (18)0.062 (2)0.054 (2)0.0017 (16)−0.0155 (16)−0.0046 (16)
C20.053 (2)0.069 (2)0.057 (2)0.0039 (17)−0.0191 (17)−0.0018 (18)
C30.052 (2)0.082 (3)0.074 (3)0.009 (2)−0.0128 (19)−0.023 (2)
C40.059 (2)0.100 (3)0.061 (2)0.005 (2)−0.0171 (19)−0.021 (2)
C50.080 (3)0.100 (3)0.057 (2)0.012 (3)−0.031 (2)−0.003 (2)
C60.068 (2)0.076 (3)0.062 (2)0.012 (2)−0.022 (2)−0.006 (2)
C70.0542 (19)0.057 (2)0.0438 (17)0.0082 (16)−0.0043 (15)−0.0086 (15)
C80.078 (3)0.061 (2)0.069 (3)0.012 (2)−0.023 (2)0.002 (2)
C90.093 (3)0.049 (2)0.081 (3)−0.002 (2)−0.021 (3)0.002 (2)
C100.070 (2)0.063 (2)0.053 (2)−0.0071 (19)−0.0078 (18)−0.0127 (17)
C110.060 (2)0.067 (2)0.057 (2)0.0023 (18)−0.0169 (18)−0.0022 (18)
C120.060 (2)0.057 (2)0.060 (2)−0.0021 (17)−0.0172 (18)0.0043 (17)
C130.090 (3)0.089 (3)0.090 (4)−0.026 (3)−0.016 (3)−0.016 (3)
Cl30.0841 (7)0.0865 (7)0.0462 (5)−0.0316 (6)−0.0080 (4)0.0011 (4)
Cl40.0800 (7)0.0603 (6)0.0840 (7)−0.0256 (5)−0.0216 (6)0.0062 (5)
S20.0471 (4)0.0448 (4)0.0568 (5)−0.0018 (3)−0.0079 (4)−0.0015 (3)
O30.0538 (15)0.0551 (14)0.0782 (18)0.0029 (12)−0.0128 (13)0.0086 (13)
O40.0651 (16)0.0577 (15)0.0622 (16)−0.0044 (12)−0.0030 (13)−0.0150 (12)
N20.0461 (15)0.0553 (16)0.0491 (16)−0.0061 (13)−0.0081 (13)0.0025 (13)
C140.0416 (16)0.0457 (17)0.0527 (19)−0.0020 (13)−0.0105 (14)−0.0005 (14)
C150.0486 (18)0.057 (2)0.0487 (18)−0.0069 (15)−0.0093 (15)0.0005 (15)
C160.057 (2)0.060 (2)0.057 (2)−0.0105 (17)−0.0175 (17)−0.0031 (17)
C170.0493 (19)0.0492 (19)0.065 (2)−0.0071 (15)−0.0159 (16)0.0043 (16)
C180.058 (2)0.058 (2)0.053 (2)−0.0061 (17)−0.0100 (16)0.0081 (16)
C190.0539 (19)0.057 (2)0.0463 (18)−0.0040 (15)−0.0112 (15)0.0000 (15)
C200.0466 (17)0.0426 (16)0.0521 (19)−0.0055 (13)−0.0077 (14)−0.0021 (14)
C21A0.070 (8)0.107 (11)0.049 (6)0.004 (7)−0.004 (5)−0.021 (7)
C22A0.065 (8)0.095 (11)0.090 (8)0.027 (7)−0.019 (6)−0.042 (8)
C230.067 (2)0.055 (2)0.072 (3)0.0029 (18)−0.024 (2)−0.0080 (19)
C24A0.063 (7)0.085 (9)0.075 (9)0.013 (7)−0.036 (6)−0.033 (8)
C25A0.060 (8)0.077 (8)0.078 (10)0.008 (6)−0.013 (7)−0.043 (7)
C260.096 (4)0.069 (3)0.113 (4)0.023 (3)−0.050 (3)−0.017 (3)
Cl5A0.147 (9)0.086 (4)0.070 (4)−0.018 (4)−0.009 (4)−0.025 (3)
Cl6A0.089 (2)0.157 (6)0.050 (2)0.004 (4)−0.0106 (16)0.014 (3)
S30.0698 (6)0.0593 (5)0.0463 (5)0.0149 (4)−0.0109 (4)−0.0049 (4)
O50.084 (2)0.084 (2)0.0546 (16)0.0286 (16)−0.0223 (15)−0.0103 (14)
O60.088 (2)0.0569 (16)0.0748 (19)0.0049 (15)−0.0128 (16)−0.0022 (14)
N30.065 (2)0.074 (2)0.0438 (16)0.0119 (16)−0.0105 (14)−0.0147 (15)
C270.058 (2)0.066 (2)0.046 (2)0.017 (2)−0.0119 (17)−0.0069 (17)
C28A0.076 (14)0.099 (19)0.044 (11)0.030 (11)−0.018 (9)−0.028 (10)
C29A0.082 (12)0.093 (13)0.093 (16)0.019 (9)−0.046 (10)0.024 (10)
C30A0.050 (9)0.116 (13)0.057 (7)0.043 (8)−0.009 (5)0.025 (7)
C31A0.086 (11)0.142 (17)0.049 (10)0.029 (11)−0.033 (9)−0.042 (11)
C32A0.021 (7)0.098 (9)0.067 (7)0.026 (6)0.001 (5)−0.023 (5)
C330.059 (2)0.055 (2)0.0456 (18)0.0024 (16)−0.0003 (16)−0.0022 (15)
C340.072 (2)0.055 (2)0.055 (2)0.0047 (18)−0.0071 (18)−0.0116 (17)
C350.065 (2)0.065 (2)0.066 (2)−0.0008 (19)−0.0099 (19)−0.0027 (19)
C360.070 (3)0.059 (2)0.057 (2)0.0066 (19)0.0019 (19)0.0057 (18)
C370.082 (3)0.059 (2)0.077 (3)0.013 (2)−0.004 (2)−0.019 (2)
C380.079 (3)0.063 (2)0.065 (2)0.002 (2)−0.009 (2)−0.0191 (19)
C390.074 (3)0.091 (4)0.105 (4)0.021 (3)0.004 (3)0.003 (3)
Cl70.0976 (9)0.0855 (8)0.1174 (10)−0.0483 (7)−0.0412 (8)0.0371 (7)
Cl80.0762 (7)0.1067 (9)0.0576 (6)−0.0272 (6)−0.0043 (5)−0.0050 (5)
S40.0627 (6)0.0440 (5)0.0844 (7)−0.0090 (4)−0.0124 (5)−0.0004 (4)
O70.091 (2)0.0576 (17)0.104 (3)−0.0044 (16)−0.0139 (19)−0.0260 (17)
O80.0742 (19)0.0536 (16)0.113 (3)−0.0054 (14)−0.0187 (18)0.0211 (16)
N40.0540 (18)0.0605 (18)0.067 (2)−0.0127 (14)−0.0109 (16)0.0021 (16)
C400.0480 (18)0.0441 (17)0.063 (2)−0.0017 (14)−0.0094 (16)0.0009 (15)
C410.0443 (18)0.056 (2)0.059 (2)−0.0050 (15)−0.0094 (15)0.0009 (16)
C420.054 (2)0.057 (2)0.071 (2)−0.0050 (17)−0.0201 (18)−0.0024 (18)
C430.0454 (19)0.055 (2)0.081 (3)−0.0094 (16)−0.0191 (18)0.0176 (19)
C440.0485 (19)0.068 (2)0.064 (2)0.0012 (17)−0.0050 (17)0.0138 (19)
C450.057 (2)0.056 (2)0.061 (2)0.0063 (17)−0.0085 (17)−0.0060 (17)
C460.0447 (18)0.055 (2)0.069 (2)−0.0149 (15)−0.0070 (16)−0.0100 (17)
C470.085 (3)0.062 (2)0.069 (3)0.003 (2)−0.012 (2)−0.018 (2)
C480.084 (3)0.074 (3)0.057 (2)−0.003 (2)−0.011 (2)−0.011 (2)
C490.052 (2)0.075 (3)0.066 (2)−0.0033 (18)−0.0064 (18)−0.007 (2)
C500.068 (3)0.102 (4)0.074 (3)0.021 (3)−0.004 (2)−0.019 (3)
C510.067 (3)0.099 (3)0.054 (2)0.004 (2)−0.0002 (19)−0.015 (2)
C520.078 (3)0.095 (4)0.093 (4)0.011 (3)−0.015 (3)0.003 (3)
C21B0.064 (7)0.073 (7)0.054 (7)0.006 (5)−0.018 (5)−0.024 (5)
C22B0.069 (8)0.056 (6)0.088 (8)0.010 (5)−0.032 (6)−0.033 (5)
C24B0.070 (8)0.099 (10)0.051 (5)0.003 (7)−0.019 (6)−0.003 (6)
C25B0.058 (8)0.097 (11)0.054 (6)0.019 (7)−0.014 (6)−0.006 (7)
C28B0.051 (9)0.058 (11)0.075 (15)−0.004 (8)0.002 (8)0.010 (8)
C29B0.051 (8)0.117 (15)0.053 (10)−0.015 (8)0.021 (6)−0.016 (8)
C30B0.040 (6)0.124 (14)0.031 (5)0.043 (9)−0.005 (4)0.010 (6)
C31B0.060 (7)0.115 (11)0.026 (6)0.007 (6)−0.014 (5)−0.031 (7)
C32B0.026 (8)0.086 (6)0.042 (7)0.033 (6)−0.006 (5)−0.021 (4)
Cl5B0.095 (4)0.100 (5)0.076 (4)−0.028 (3)−0.010 (3)−0.012 (3)
Cl6B0.080 (2)0.174 (6)0.0448 (16)−0.013 (4)−0.0067 (14)0.004 (4)

Geometric parameters (Å, °)

Cl1—C21.731 (4)N3—H3N0.82 (3)
Cl2—C41.730 (4)C27—C28A1.327 (19)
S1—O11.421 (3)C27—C32A1.384 (13)
S1—O21.434 (3)C27—C32B1.394 (11)
S1—N11.600 (4)C27—C28B1.420 (15)
S1—C11.773 (4)C28A—C29A1.403 (14)
N1—C71.433 (5)C29A—C30A1.382 (15)
N1—H1N0.83 (3)C29A—H29A0.9300
C1—C61.379 (6)C30A—C31A1.372 (16)
C1—C21.381 (5)C31A—C32A1.370 (15)
C2—C31.382 (6)C31A—H31A0.9300
C3—C41.358 (7)C32A—H32A0.9300
C3—H30.9300C33—C341.361 (6)
C4—C51.371 (7)C33—C381.392 (5)
C5—C61.381 (6)C34—C351.386 (6)
C5—H50.9300C34—H340.9300
C6—H60.9300C35—C361.380 (6)
C7—C121.365 (5)C35—H350.9300
C7—C81.373 (6)C36—C371.371 (7)
C8—C91.382 (7)C36—C391.488 (6)
C8—H80.9300C37—C381.367 (7)
C9—C101.372 (6)C37—H370.9300
C9—H90.9300C38—H380.9300
C10—C111.369 (6)C39—H39A0.9600
C10—C131.525 (6)C39—H39B0.9600
C11—C121.387 (6)C39—H39C0.9600
C11—H110.9300Cl7—C431.729 (4)
C12—H120.9300Cl8—C411.726 (4)
C13—H13A0.9600S4—O71.419 (4)
C13—H13B0.9600S4—O81.427 (3)
C13—H13C0.9600S4—N41.620 (4)
Cl3—C151.727 (4)S4—C401.775 (4)
Cl4—C171.722 (4)N4—C461.411 (5)
S2—O41.417 (3)N4—H4N0.86 (3)
S2—O31.426 (3)C40—C451.374 (5)
S2—N21.609 (3)C40—C411.386 (5)
S2—C141.782 (3)C41—C421.369 (5)
N2—C201.423 (5)C42—C431.364 (6)
N2—H2N0.85 (3)C42—H420.9300
C14—C151.383 (5)C43—C441.378 (6)
C14—C191.386 (5)C44—C451.386 (6)
C15—C161.380 (5)C44—H440.9300
C16—C171.382 (5)C45—H450.9300
C16—H160.9300C46—C511.381 (6)
C17—C181.365 (6)C46—C471.382 (6)
C18—C191.388 (5)C47—C481.373 (7)
C18—H180.9300C47—H470.9300
C19—H190.9300C48—C491.368 (6)
C20—C21B1.368 (10)C48—H480.9300
C20—C21A1.376 (11)C49—C501.371 (7)
C20—C25B1.379 (18)C49—C521.503 (7)
C20—C25A1.382 (18)C50—C511.393 (7)
C21A—C22A1.389 (13)C50—H500.9300
C21A—H21A0.9300C51—H510.9300
C22A—C231.369 (12)C52—H52A0.9600
C22A—H22A0.9300C52—H52B0.9600
C23—C22B1.355 (11)C52—H52C0.9600
C23—C24B1.366 (12)C21B—C22B1.388 (12)
C23—C24A1.371 (11)C21B—H21B0.9300
C23—C261.515 (6)C22B—H22B0.9300
C24A—C25A1.372 (13)C24B—C25B1.371 (12)
C24A—H24A0.9300C24B—H24B0.9300
C25A—H25A0.9300C25B—H25B0.9300
C26—H26A0.9600C28B—C29B1.404 (13)
C26—H26B0.9600C28B—Cl5B1.721 (12)
C26—H26C0.9600C29B—C30B1.390 (14)
Cl5A—C28A1.728 (12)C29B—H29B0.9300
Cl6A—C30A1.734 (12)C30B—C31B1.375 (16)
S3—O51.423 (3)C30B—Cl6B1.744 (10)
S3—O61.424 (3)C31B—C32B1.375 (14)
S3—N31.603 (3)C31B—H31B0.9300
S3—C271.775 (4)C32B—H32B0.9300
N3—C331.419 (5)
O1—S1—O2119.00 (19)C28A—C27—C32B115.8 (10)
O1—S1—N1109.73 (18)C32A—C27—C32B16.0 (9)
O2—S1—N1105.10 (18)C28A—C27—C28B4(2)
O1—S1—C1106.05 (18)C32A—C27—C28B124.1 (12)
O2—S1—C1108.63 (17)C32B—C27—C28B117.5 (10)
N1—S1—C1107.94 (19)C28A—C27—S3124.3 (6)
C7—N1—S1127.5 (3)C32A—C27—S3114.0 (11)
C7—N1—H1N120 (3)C32B—C27—S3118.9 (9)
S1—N1—H1N107 (3)C28B—C27—S3121.8 (6)
C6—C1—C2117.9 (4)C27—C28A—C29A126.8 (15)
C6—C1—S1118.5 (3)C27—C28A—Cl5A123.5 (9)
C2—C1—S1123.5 (3)C29A—C28A—Cl5A109.6 (18)
C1—C2—C3120.9 (4)C30A—C29A—C28A113.4 (17)
C1—C2—Cl1121.7 (3)C30A—C29A—H29A123.3
C3—C2—Cl1117.4 (3)C28A—C29A—H29A123.3
C4—C3—C2119.6 (4)C31A—C30A—C29A112.6 (17)
C4—C3—H3120.2C31A—C30A—Cl6A131.5 (19)
C2—C3—H3120.2C29A—C30A—Cl6A113.5 (14)
C3—C4—C5121.3 (4)C32A—C31A—C30A133 (2)
C3—C4—Cl2118.5 (4)C32A—C31A—H31A113.4
C5—C4—Cl2120.2 (4)C30A—C31A—H31A113.4
C4—C5—C6118.4 (4)C31A—C32A—C27106.5 (17)
C4—C5—H5120.8C31A—C32A—H32A126.7
C6—C5—H5120.8C27—C32A—H32A126.7
C1—C6—C5121.9 (4)C34—C33—C38119.0 (4)
C1—C6—H6119.1C34—C33—N3123.9 (3)
C5—C6—H6119.1C38—C33—N3117.1 (4)
C12—C7—C8119.8 (4)C33—C34—C35120.0 (4)
C12—C7—N1123.3 (4)C33—C34—H34120.0
C8—C7—N1116.9 (4)C35—C34—H34120.0
C7—C8—C9119.9 (4)C36—C35—C34121.9 (4)
C7—C8—H8120.1C36—C35—H35119.1
C9—C8—H8120.1C34—C35—H35119.1
C10—C9—C8121.2 (4)C37—C36—C35116.7 (4)
C10—C9—H9119.4C37—C36—C39121.6 (4)
C8—C9—H9119.4C35—C36—C39121.7 (5)
C11—C10—C9118.0 (4)C38—C37—C36122.7 (4)
C11—C10—C13121.4 (4)C38—C37—H37118.6
C9—C10—C13120.6 (4)C36—C37—H37118.6
C10—C11—C12121.6 (4)C37—C38—C33119.6 (4)
C10—C11—H11119.2C37—C38—H38120.2
C12—C11—H11119.2C33—C38—H38120.2
C7—C12—C11119.5 (4)C36—C39—H39A109.5
C7—C12—H12120.2C36—C39—H39B109.5
C11—C12—H12120.2H39A—C39—H39B109.5
C10—C13—H13A109.5C36—C39—H39C109.5
C10—C13—H13B109.5H39A—C39—H39C109.5
H13A—C13—H13B109.5H39B—C39—H39C109.5
C10—C13—H13C109.5O7—S4—O8119.1 (2)
H13A—C13—H13C109.5O7—S4—N4109.8 (2)
H13B—C13—H13C109.5O8—S4—N4106.0 (2)
O4—S2—O3119.20 (17)O7—S4—C40105.50 (19)
O4—S2—N2109.43 (17)O8—S4—C40110.06 (19)
O3—S2—N2105.88 (16)N4—S4—C40105.68 (17)
O4—S2—C14105.53 (16)C46—N4—S4123.7 (3)
O3—S2—C14108.17 (17)C46—N4—H4N121 (3)
N2—S2—C14108.26 (16)S4—N4—H4N109 (3)
C20—N2—S2123.1 (2)C45—C40—C41119.1 (3)
C20—N2—H2N116 (3)C45—C40—S4118.4 (3)
S2—N2—H2N116 (3)C41—C40—S4122.5 (3)
C15—C14—C19118.7 (3)C42—C41—C40120.7 (4)
C15—C14—S2123.5 (3)C42—C41—Cl8117.7 (3)
C19—C14—S2117.6 (3)C40—C41—Cl8121.6 (3)
C16—C15—C14120.8 (3)C43—C42—C41119.1 (4)
C16—C15—Cl3117.7 (3)C43—C42—H42120.5
C14—C15—Cl3121.5 (3)C41—C42—H42120.5
C15—C16—C17119.0 (4)C42—C43—C44122.2 (4)
C15—C16—H16120.5C42—C43—Cl7118.6 (3)
C17—C16—H16120.5C44—C43—Cl7119.3 (3)
C18—C17—C16121.6 (3)C43—C44—C45117.9 (4)
C18—C17—Cl4120.4 (3)C43—C44—H44121.0
C16—C17—Cl4118.0 (3)C45—C44—H44121.0
C17—C18—C19118.7 (3)C40—C45—C44121.0 (4)
C17—C18—H18120.6C40—C45—H45119.5
C19—C18—H18120.6C44—C45—H45119.5
C14—C19—C18121.0 (3)C51—C46—C47119.2 (4)
C14—C19—H19119.5C51—C46—N4117.8 (4)
C18—C19—H19119.5C47—C46—N4123.0 (4)
C21B—C20—C21A25.7 (7)C48—C47—C46119.0 (4)
C21B—C20—C25B112.6 (9)C48—C47—H47120.5
C21A—C20—C25B120.9 (10)C46—C47—H47120.5
C21B—C20—C25A116.3 (9)C49—C48—C47123.9 (4)
C21A—C20—C25A113.0 (9)C49—C48—H48118.1
C25B—C20—C25A23.9 (8)C47—C48—H48118.1
C21B—C20—N2121.4 (7)C48—C49—C50116.0 (4)
C21A—C20—N2117.7 (8)C48—C49—C52121.9 (4)
C25B—C20—N2121.3 (7)C50—C49—C52122.1 (4)
C25A—C20—N2122.3 (7)C49—C50—C51122.6 (4)
C20—C21A—C22A117.6 (13)C49—C50—H50118.7
C20—C21A—H21A121.2C51—C50—H50118.7
C22A—C21A—H21A121.2C46—C51—C50119.3 (4)
C23—C22A—C21A124.0 (13)C46—C51—H51120.4
C23—C22A—H22A118.0C50—C51—H51120.4
C21A—C22A—H22A118.0C49—C52—H52A109.5
C22B—C23—C24B110.0 (10)C49—C52—H52B109.5
C22B—C23—C22A27.4 (7)H52A—C52—H52B109.5
C24B—C23—C22A115.0 (10)C49—C52—H52C109.5
C22B—C23—C24A119.2 (10)H52A—C52—H52C109.5
C24B—C23—C24A23.7 (9)H52B—C52—H52C109.5
C22A—C23—C24A112.2 (10)C20—C21B—C22B121.9 (12)
C22B—C23—C26121.0 (7)C20—C21B—H21B119.1
C24B—C23—C26122.7 (8)C22B—C21B—H21B119.1
C22A—C23—C26122.2 (7)C23—C22B—C21B120.2 (12)
C24A—C23—C26119.7 (8)C23—C22B—H22B119.9
C23—C24A—C25A119.7 (13)C21B—C22B—H22B119.9
C23—C24A—H24A120.2C23—C24B—C25B124.7 (14)
C25A—C24A—H24A120.2C23—C24B—H24B117.6
C24A—C25A—C20122.5 (13)C25B—C24B—H24B117.6
C24A—C25A—H25A118.7C24B—C25B—C20117.8 (15)
C20—C25A—H25A118.7C24B—C25B—H25B121.1
C23—C26—H26A109.5C20—C25B—H25B121.1
C23—C26—H26B109.5C29B—C28B—C27114.7 (14)
H26A—C26—H26B109.5C29B—C28B—Cl5B123.3 (15)
C23—C26—H26C109.5C27—C28B—Cl5B121.9 (8)
H26A—C26—H26C109.5C30B—C29B—C28B119.5 (15)
H26B—C26—H26C109.5C30B—C29B—H29B120.3
O5—S3—O6118.92 (19)C28B—C29B—H29B120.3
O5—S3—N3105.43 (18)C31B—C30B—C29B126.9 (13)
O6—S3—N3109.4 (2)C31B—C30B—Cl6B110.0 (14)
O5—S3—C27107.92 (19)C29B—C30B—Cl6B120.9 (12)
O6—S3—C27106.1 (2)C30B—C31B—C32B107.2 (18)
N3—S3—C27108.71 (18)C30B—C31B—H31B126.4
C33—N3—S3127.8 (3)C32B—C31B—H31B126.4
C33—N3—H3N117 (4)C31B—C32B—C27129.0 (18)
S3—N3—H3N114 (4)C31B—C32B—H32B115.5
C28A—C27—C32A121.6 (12)C27—C32B—H32B115.5
O1—S1—N1—C7−54.5 (4)C32B—C27—C28A—Cl5A−173.3 (18)
O2—S1—N1—C7176.4 (3)C28B—C27—C28A—Cl5A−56 (23)
C1—S1—N1—C760.6 (4)S3—C27—C28A—Cl5A−5(3)
O1—S1—C1—C6−6.6 (4)C27—C28A—C29A—C30A14 (4)
O2—S1—C1—C6122.4 (3)Cl5A—C28A—C29A—C30A−169.1 (17)
N1—S1—C1—C6−124.2 (3)C28A—C29A—C30A—C31A−17 (3)
O1—S1—C1—C2176.5 (3)C28A—C29A—C30A—Cl6A178.3 (17)
O2—S1—C1—C2−54.5 (4)C29A—C30A—C31A—C32A28 (5)
N1—S1—C1—C259.0 (4)Cl6A—C30A—C31A—C32A−171 (3)
C6—C1—C2—C30.9 (6)C30A—C31A—C32A—C27−25 (5)
S1—C1—C2—C3177.8 (3)C28A—C27—C32A—C31A16 (3)
C6—C1—C2—Cl1−179.4 (3)C32B—C27—C32A—C31A−57 (6)
S1—C1—C2—Cl1−2.5 (5)C28B—C27—C32A—C31A12 (3)
C1—C2—C3—C4−0.7 (7)S3—C27—C32A—C31A−169 (2)
Cl1—C2—C3—C4179.6 (4)S3—N3—C33—C3416.6 (6)
C2—C3—C4—C50.7 (7)S3—N3—C33—C38−165.1 (3)
C2—C3—C4—Cl2−179.5 (3)C38—C33—C34—C35−1.1 (6)
C3—C4—C5—C6−0.9 (8)N3—C33—C34—C35177.1 (4)
Cl2—C4—C5—C6179.4 (4)C33—C34—C35—C36−0.1 (6)
C2—C1—C6—C5−1.1 (7)C34—C35—C36—C371.2 (6)
S1—C1—C6—C5−178.2 (4)C34—C35—C36—C39−177.5 (4)
C4—C5—C6—C11.1 (7)C35—C36—C37—C38−1.0 (7)
S1—N1—C7—C1228.6 (5)C39—C36—C37—C38177.6 (5)
S1—N1—C7—C8−154.0 (3)C36—C37—C38—C33−0.2 (7)
C12—C7—C8—C90.5 (6)C34—C33—C38—C371.3 (6)
N1—C7—C8—C9−177.0 (4)N3—C33—C38—C37−177.1 (4)
C7—C8—C9—C10−0.7 (7)O7—S4—N4—C46−60.3 (4)
C8—C9—C10—C110.5 (7)O8—S4—N4—C46169.8 (3)
C8—C9—C10—C13178.8 (4)C40—S4—N4—C4653.0 (4)
C9—C10—C11—C12−0.2 (6)O7—S4—C40—C45−0.1 (4)
C13—C10—C11—C12−178.4 (4)O8—S4—C40—C45129.6 (3)
C8—C7—C12—C11−0.2 (6)N4—S4—C40—C45−116.5 (3)
N1—C7—C12—C11177.1 (4)O7—S4—C40—C41178.1 (3)
C10—C11—C12—C70.1 (6)O8—S4—C40—C41−52.3 (4)
O4—S2—N2—C2054.9 (3)N4—S4—C40—C4161.7 (4)
O3—S2—N2—C20−175.5 (3)C45—C40—C41—C42−1.6 (6)
C14—S2—N2—C20−59.7 (3)S4—C40—C41—C42−179.8 (3)
O4—S2—C14—C15−178.0 (3)C45—C40—C41—Cl8178.9 (3)
O3—S2—C14—C1553.4 (3)S4—C40—C41—Cl80.7 (5)
N2—S2—C14—C15−60.9 (3)C40—C41—C42—C430.8 (6)
O4—S2—C14—C197.4 (3)Cl8—C41—C42—C43−179.7 (3)
O3—S2—C14—C19−121.2 (3)C41—C42—C43—C440.3 (6)
N2—S2—C14—C19124.5 (3)C41—C42—C43—Cl7−178.8 (3)
C19—C14—C15—C161.5 (5)C42—C43—C44—C45−0.6 (6)
S2—C14—C15—C16−173.1 (3)Cl7—C43—C44—C45178.6 (3)
C19—C14—C15—Cl3−178.3 (3)C41—C40—C45—C441.4 (6)
S2—C14—C15—Cl37.1 (5)S4—C40—C45—C44179.6 (3)
C14—C15—C16—C170.9 (6)C43—C44—C45—C40−0.3 (6)
Cl3—C15—C16—C17−179.3 (3)S4—N4—C46—C51−141.1 (4)
C15—C16—C17—C18−2.5 (6)S4—N4—C46—C4741.4 (5)
C15—C16—C17—Cl4176.5 (3)C51—C46—C47—C48−0.1 (6)
C16—C17—C18—C191.7 (6)N4—C46—C47—C48177.4 (4)
Cl4—C17—C18—C19−177.3 (3)C46—C47—C48—C49−1.1 (7)
C15—C14—C19—C18−2.3 (5)C47—C48—C49—C500.8 (7)
S2—C14—C19—C18172.5 (3)C47—C48—C49—C52−179.3 (5)
C17—C18—C19—C140.8 (6)C48—C49—C50—C510.8 (8)
S2—N2—C20—C21B112.0 (7)C52—C49—C50—C51−179.2 (5)
S2—N2—C20—C21A141.3 (7)C47—C46—C51—C501.5 (7)
S2—N2—C20—C25B−41.9 (8)N4—C46—C51—C50−176.1 (4)
S2—N2—C20—C25A−70.1 (8)C49—C50—C51—C46−1.9 (8)
C21B—C20—C21A—C22A−77 (3)C21A—C20—C21B—C22B89 (3)
C25B—C20—C21A—C22A0.5 (18)C25B—C20—C21B—C22B−25.2 (15)
C25A—C20—C21A—C22A25.8 (16)C25A—C20—C21B—C22B0.7 (16)
N2—C20—C21A—C22A177.3 (10)N2—C20—C21B—C22B178.8 (9)
C20—C21A—C22A—C231(2)C24B—C23—C22B—C21B30.1 (16)
C21A—C22A—C23—C22B85 (3)C22A—C23—C22B—C21B−76 (2)
C21A—C22A—C23—C24B−0.5 (19)C24A—C23—C22B—C21B6.1 (17)
C21A—C22A—C23—C24A−26.2 (18)C26—C23—C22B—C21B−177.0 (10)
C21A—C22A—C23—C26−179.0 (11)C20—C21B—C22B—C23−3.9 (19)
C22B—C23—C24A—C25A−5.1 (18)C22B—C23—C24B—C25B−29.9 (18)
C24B—C23—C24A—C25A−78 (3)C22A—C23—C24B—C25B−0.8 (19)
C22A—C23—C24A—C25A24.4 (17)C24A—C23—C24B—C25B88 (4)
C26—C23—C24A—C25A177.9 (11)C26—C23—C24B—C25B177.7 (12)
C23—C24A—C25A—C202(2)C23—C24B—C25B—C202(2)
C21B—C20—C25A—C24A0.3 (17)C21B—C20—C25B—C24B25.7 (16)
C21A—C20—C25A—C24A−27.9 (17)C21A—C20—C25B—C24B−1.6 (18)
C25B—C20—C25A—C24A87 (3)C25A—C20—C25B—C24B−78 (3)
N2—C20—C25A—C24A−177.8 (11)N2—C20—C25B—C24B−178.3 (10)
O5—S3—N3—C33179.4 (3)C28A—C27—C28B—C29B−51 (23)
O6—S3—N3—C33−51.6 (4)C32A—C27—C28B—C29B−4(3)
C27—S3—N3—C3363.9 (4)C32B—C27—C28B—C29B13 (3)
O5—S3—C27—C28A−56.0 (16)S3—C27—C28B—C29B177.6 (14)
O6—S3—C27—C28A175.5 (16)C28A—C27—C28B—Cl5B126 (27)
N3—S3—C27—C28A57.8 (16)C32A—C27—C28B—Cl5B173.3 (16)
O5—S3—C27—C32A128.8 (7)C32B—C27—C28B—Cl5B−169.8 (17)
O6—S3—C27—C32A0.3 (8)S3—C27—C28B—Cl5B−5(3)
N3—S3—C27—C32A−117.4 (7)C27—C28B—C29B—C30B−15 (3)
O5—S3—C27—C32B111.8 (7)Cl5B—C28B—C29B—C30B167.6 (19)
O6—S3—C27—C32B−16.7 (7)C28B—C29B—C30B—C31B22 (4)
N3—S3—C27—C32B−134.4 (7)C28B—C29B—C30B—Cl6B−176.6 (18)
O5—S3—C27—C28B−52.6 (15)C29B—C30B—C31B—C32B−22 (4)
O6—S3—C27—C28B178.8 (15)Cl6B—C30B—C31B—C32B175.2 (19)
N3—S3—C27—C28B61.2 (15)C30B—C31B—C32B—C2720 (4)
C32A—C27—C28A—C29A−14 (4)C28A—C27—C32B—C31B−14 (3)
C32B—C27—C28A—C29A3(3)C32A—C27—C32B—C31B101 (8)
C28B—C27—C28A—C29A121 (27)C28B—C27—C32B—C31B−17 (3)
S3—C27—C28A—C29A171.5 (19)S3—C27—C32B—C31B177 (2)
C32A—C27—C28A—Cl5A169.7 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.83 (3)2.26 (3)3.079 (4)169 (5)
N2—H2N···O3ii0.85 (3)2.24 (3)3.080 (4)169 (4)
N3—H3N···O5iii0.82 (3)2.14 (3)2.956 (5)178 (5)
N4—H4N···O8iv0.86 (3)2.37 (3)3.226 (5)177 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2592).

References

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