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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-(4-Amino­phenyl­sulfon­yl)aniline–1,3,5-tri­nitro­benzene (1/2)

aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au

(Received 15 December 2011; accepted 14 January 2012; online 21 January 2012)

The asymmetric unit of the title co-crystalline 1:2 adduct, C12H12N2O2·2C6H3N3O6, contains two independent mol­ecules of bis­(4-amino­phen­yl) sulfone (the drug Dapsone) and four mol­ecules of 1,3,5-trinitro­benzene and is extended into a two-dimensional hydrogen-bonded network structure through amino N—H⋯O hydrogen-bonding associations with nitro O-atom acceptors. In the two independent Dapsone mol­ecules, the inter-ring dihedral anges are 69.6 (3) and 63.63 (9)°. Aromatic ππ inter­actions are also found between one of the Dapsone aromatic rings and a trinitro­benzene ring [minimum ring centroid separation = 3.596 (3) Å]. A 4-amino­phenyl ring moiety of one of the Dapsone mol­ecules and two nitro groups of a trinitro­benzene are disordered in a 50:50 ratio.

Related literature

For drug applications of Dapsone, see: Wilson et al. (1991[Wilson, J. D., Braunwald, E., Isselbacher, K. J., Petersdorf, R. G., Martin, J. B., Fauci, A. S. & Root, R. K. (1991). Harrison's Principles of Internal Medicine 12th ed., pp. 320, 647-648, 787. New York: McGraw-Hill.]). For the structures of Dapsone and its partial hydrate, see: Dickenson et al. (1970[Dickenson, C., Stewart, J. M. & Ammon, H. L. (1970). J. Chem. Soc. Chem. Commun. pp. 920-921.]); Kus'mina et al. (1981[Kus'mina, L. G., Struchkov, Yu. T., Novozhilova, N. V. & Tudorovskaya, G. L. (1981). Kristallografiya, 26, 690-694.]). For the deca­rboxylation of 2,4,6-trinitro­benzoic acid and resultant co-crystal adduct structure, see: Smith et al. (2002[Smith, G., Wermuth, U. D. & White, J. M. (2002). Acta Cryst. E58, o1130-o1132.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O2S·2C6H3N3O6

  • Mr = 674.52

  • Triclinic, [P \overline 1]

  • a = 8.3196 (2) Å

  • b = 18.3524 (5) Å

  • c = 18.6285 (5) Å

  • α = 83.577 (2)°

  • β = 87.539 (2)°

  • γ = 88.237 (2)°

  • V = 2822.86 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 200 K

  • 0.35 × 0.15 × 0.10 mm

Data collection
  • Oxford Diffraction Gemini-S Ultra CCD detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.932, Tmax = 0.980

  • 34593 measured reflections

  • 11078 independent reflections

  • 6613 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.077

  • S = 0.94

  • 11078 reflections

  • 880 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4A—H41A⋯O52Di 0.88 2.49 3.324 (4) 160
N41A—H43A⋯O12Dii 0.88 2.46 3.248 (2) 149
N41A—H44A⋯O52Ciii 0.88 2.26 3.096 (2) 158
N4X—H4X1⋯O51Eiv 0.88 2.46 3.267 (4) 152
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Dapsone [4-(4-aminophenylsulfonyl)aniline] is a very weak Lewis base which finds use as an anti-leprotic, anti-malarial and leprostatic drug (Wilson et al., 1991). The structure of the anhydrous parent compound is known (Dickenson et al., 1970) and its partial (1/3) hydrate has been reported (Kus'mina et al., 1981). However, no compounds or adducts of Dapsone are found in the crystallographic literature. Our attempted preparation of Dapsone with 2,4,6-trinitrobenzoic acid (TNBA) resulted in the title compound, the TNB adduct molecules resulting from the common facile decarboxylation of the parent acid (Smith et al., 2002).

The asymmetric unit of the title adduct (Fig. 1) contains two independent molecules of Dapsone (A and B) and four molecules of 1,3,5-trinitrobenzene (TNB) (CF) and is extended into a two-dimensional hydrogen-bonded network structure (Fig. 2) through amino N—H···O hydrogen-bond associations with nitro O-atom acceptors (Table 1). No interactions with sulfone O-atom acceptors are present. A weak ππ interaction is also found between one of the Dapsone aromatic ring moieties (C1A–C6A) and a TNB F ring [minimum ring centroid separation 3.719 (4) Å]. A 4-aminophenyl ring moiety of one of the Dapsone molecules (C1A–C6A, N4A) is 50% disordered, with the ring of the second component (C1X–C6X, N4X) giving a ring centroid separation of 3.596 (3) Å with the trinitrobenzene A ring. Two of the nitro groups of the A molecule are Also 50% disordered. In the two independent Dapsone molecules the inter-ring dihedral angles are 69.6 (3)° (A) and 63.63 (9)° (B) which compare with 77.3° in the anhydrous parent Dapsone molecule (Dickenson et al., 1970) and 88.1, 75.8 and 74.7° for the three independent Dapsone molecules in the 0.33 hydrate structure (Kus'mina et al., 1981).

Related literature top

For drug applications of Dapsone, see: Wilson et al. (1991). For the structures of Dapsone and its partial hydrate, see: Dickenson et al. (1970); Kus'mina et al. (1981). For the decarboxylation of 2,4,6-trinitrobenzoic acid and resultant co-crystal adduct structure, see: Smith et al. (2002).

Experimental top

The title compound was formed in an attempted synthesis of a proton-transfer salt of 4-(4-aminophenylsulfonyl)aniline (Dapsone) with 2,4,6-trinitrobenzoic acid by heating 1 mmol quantities of the two reagents in 50 ml of 50% ethanol–water for 15 min under reflux. Facile decarboxylation of the acid resulted in the formation of orange needle crystals of the title Dapsone- 1,3,5-trinitrobenzene co-crystal [m.p. 414–415 K], after room-temperature evaporation of the solvent.

Refinement top

All H atoms were included at calculated positions [N—H = 0.88 Å; C—H = 0.95 Å] and treated as riding, with Uiso(H) = 1.2Ueq(N/C). No reasonable acceptor atoms could be found for three of the H-atoms on separate amino groups (H42A, H42B and H44B).The atoms (C1–C6, N4) of Dapsone molecule A were disordered over two sites in a 50:50 ratio. Two nitro groups of the π-associated TNB F molecule (N11, O11, O12; N51, O51, O52) were also found to be similarly disordered in a 50:50 ratio.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular conformation and atom-numbering scheme for the two Dapsone molecules (A and B) and the four TNB molecules (CF) in the asymmetric unit of the title co-crystal. The 50% disordered ring component [C1X–C6X, N4X] of the A ring is shown in dashed outline. Non-H atoms are shown as 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The hydrogen-bonding viewed down the a axial direction of the unit cell. The disordered ring component of the A Dapsone molecule is omitted together with non-interactive hydrogen atoms while hydrogen bonds are shown as dashed lines. Symmetry codes: i -x+1, -y+1, -z; ii -x+1, -y+1, -z+1; iii -x+2, -y+1, -z+1; iv x-1, y-1, z; v -x+2, -y+1, -z.
4-(4-Aminophenylsulfonyl)aniline–1,3,5-trinitrobenzene (1/2) top
Crystal data top
C12H12N2O2S·2C6H3N3O6Z = 4
Mr = 674.52F(000) = 1384
Triclinic, P1Dx = 1.587 Mg m3
Hall symbol: -P 1Melting point > 414 K
a = 8.3196 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 18.3524 (5) ÅCell parameters from 10417 reflections
c = 18.6285 (5) Åθ = 3.2–28.8°
α = 83.577 (2)°µ = 0.20 mm1
β = 87.539 (2)°T = 200 K
γ = 88.237 (2)°Needle, orange
V = 2822.86 (13) Å30.35 × 0.15 × 0.10 mm
Data collection top
Oxford Diffraction Gemini-S Ultra CCD detector
diffractometer
11078 independent reflections
Radiation source: Enhance (Mo) X-ray source6613 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.2°
ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 2222
Tmin = 0.932, Tmax = 0.980l = 2222
34593 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0308P)2]
where P = (Fo2 + 2Fc2)/3
11078 reflections(Δ/σ)max < 0.001
880 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C12H12N2O2S·2C6H3N3O6γ = 88.237 (2)°
Mr = 674.52V = 2822.86 (13) Å3
Triclinic, P1Z = 4
a = 8.3196 (2) ÅMo Kα radiation
b = 18.3524 (5) ŵ = 0.20 mm1
c = 18.6285 (5) ÅT = 200 K
α = 83.577 (2)°0.35 × 0.15 × 0.10 mm
β = 87.539 (2)°
Data collection top
Oxford Diffraction Gemini-S Ultra CCD detector
diffractometer
11078 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
6613 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.980Rint = 0.041
34593 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 0.94Δρmax = 0.22 e Å3
11078 reflectionsΔρmin = 0.28 e Å3
880 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.38876 (6)0.76073 (3)0.25467 (3)0.0376 (2)
O1A0.28914 (15)0.82213 (8)0.27305 (7)0.0514 (5)
O11A0.31123 (19)0.69889 (8)0.23122 (9)0.0671 (6)
N4A0.8310 (4)0.9143 (2)0.0302 (2)0.0590 (10)0.500
N4X0.8262 (4)0.8502 (2)0.0096 (2)0.0590 (10)0.500
N41A0.7501 (2)0.65642 (9)0.51329 (9)0.0509 (7)
C1A0.5240 (2)0.79555 (12)0.18603 (10)0.0346 (7)
C2A0.6061 (12)0.7655 (3)0.1359 (6)0.035 (2)0.500
C2X0.5755 (12)0.7366 (3)0.1391 (6)0.035 (2)0.500
C3A0.7078 (9)0.8002 (4)0.0815 (4)0.0466 (18)0.500
C3X0.6748 (7)0.7578 (3)0.0837 (4)0.0466 (18)0.500
C4A0.7298 (6)0.8744 (3)0.0809 (3)0.0326 (16)0.500
C4X0.7245 (7)0.8276 (4)0.0681 (3)0.0326 (16)0.500
C5A0.6510 (7)0.9137 (3)0.1356 (3)0.0348 (16)0.500
C5X0.6747 (7)0.8817 (3)0.1140 (3)0.0348 (16)0.500
C6A0.5532 (17)0.8792 (6)0.1865 (8)0.029 (3)0.500
C6X0.5696 (16)0.8578 (6)0.1744 (7)0.029 (3)0.500
C11A0.4985 (2)0.72898 (10)0.33046 (10)0.0305 (7)
C21A0.5435 (2)0.77863 (11)0.37641 (11)0.0340 (7)
C31A0.6271 (2)0.75444 (11)0.43705 (10)0.0353 (7)
C41A0.6673 (2)0.68028 (10)0.45335 (10)0.0327 (7)
C51A0.6221 (2)0.63100 (10)0.40587 (10)0.0340 (7)
C61A0.5395 (2)0.65541 (11)0.34504 (10)0.0337 (7)
S1B0.68365 (6)0.26463 (3)0.26762 (3)0.0373 (2)
O1B0.77419 (15)0.25066 (7)0.20232 (8)0.0500 (5)
O11B0.77013 (16)0.27879 (7)0.32980 (8)0.0538 (6)
N4B0.2836 (2)0.53029 (11)0.18608 (15)0.0924 (12)
N41B0.3165 (2)0.00479 (10)0.35065 (13)0.0722 (8)
C1B0.5569 (2)0.34105 (10)0.24448 (11)0.0344 (7)
C2B0.5190 (2)0.36012 (11)0.17346 (12)0.0434 (8)
C3B0.4285 (3)0.42275 (13)0.15398 (14)0.0565 (9)
C4B0.3753 (3)0.46766 (12)0.20613 (18)0.0602 (9)
C5B0.4125 (3)0.44756 (13)0.27736 (16)0.0593 (10)
C6B0.5017 (2)0.38509 (12)0.29676 (13)0.0467 (8)
C11B0.5658 (2)0.18755 (10)0.29337 (11)0.0302 (7)
C21B0.5071 (2)0.14899 (11)0.24066 (11)0.0397 (8)
C31B0.4241 (2)0.08572 (12)0.25962 (13)0.0464 (9)
C41B0.3983 (2)0.05920 (11)0.33157 (14)0.0449 (8)
C51B0.4557 (2)0.09851 (11)0.38467 (12)0.0440 (8)
C61B0.5384 (2)0.16223 (11)0.36521 (11)0.0371 (7)
O11'0.5149 (8)0.8058 (3)0.0726 (3)0.0832 (19)0.500
O11F0.5379 (9)0.8540 (3)0.0733 (3)0.0832 (19)0.500
O12'0.4743 (9)0.9220 (3)0.0530 (4)0.0775 (18)0.500
O12F0.4741 (8)0.9631 (3)0.0398 (3)0.0775 (18)0.500
O31F0.1593 (2)0.97159 (10)0.17118 (12)0.0933 (9)
O32F0.0153 (2)0.89062 (9)0.20991 (9)0.0627 (7)
O51'0.0255 (11)0.6561 (7)0.1189 (6)0.064 (3)0.500
O51F0.0374 (11)0.6585 (6)0.1008 (6)0.064 (3)0.500
O52'0.1862 (9)0.6229 (4)0.0546 (4)0.073 (3)0.500
O52F0.2438 (9)0.6459 (4)0.0297 (4)0.073 (3)0.500
N11'0.4541 (13)0.8584 (4)0.0442 (5)0.058 (3)0.500
N11F0.4552 (13)0.8952 (4)0.0374 (5)0.058 (3)0.500
N31F0.0945 (2)0.91286 (11)0.16936 (12)0.0558 (8)
N51F0.1273 (4)0.67557 (15)0.07376 (17)0.0821 (14)
C1F0.3291 (3)0.8485 (2)0.01513 (13)0.0704 (12)
C2F0.2697 (3)0.89427 (14)0.06317 (14)0.0540 (9)
C3F0.1566 (2)0.86603 (12)0.11448 (12)0.0397 (8)
C4F0.1026 (2)0.79570 (11)0.11831 (11)0.0400 (8)
C5F0.1713 (3)0.75304 (13)0.06926 (13)0.0525 (9)
C6F0.2837 (4)0.7777 (2)0.01717 (14)0.0722 (13)
O11C0.9598 (3)0.61193 (11)0.26861 (10)0.1009 (9)
O12C0.8668 (2)0.72426 (11)0.26112 (9)0.0712 (7)
O31C1.07076 (18)0.88686 (8)0.41772 (8)0.0551 (6)
O32C1.25965 (19)0.84718 (8)0.48865 (9)0.0547 (6)
O51C1.36284 (19)0.58561 (9)0.53825 (9)0.0592 (6)
O52C1.2528 (3)0.51322 (9)0.47361 (10)0.0963 (9)
N11C1.1543 (2)0.83754 (9)0.44757 (10)0.0392 (6)
N31C0.9431 (3)0.67244 (14)0.29009 (11)0.0614 (9)
N51C1.2733 (3)0.57343 (11)0.49189 (11)0.0518 (8)
C1C1.0269 (2)0.68293 (12)0.35632 (11)0.0395 (8)
C2C1.0372 (2)0.75278 (11)0.37383 (11)0.0353 (7)
C3C1.1278 (2)0.76201 (10)0.43196 (10)0.0301 (7)
C4C1.2042 (2)0.70505 (10)0.47255 (10)0.0328 (7)
C5C1.1870 (2)0.63621 (11)0.45280 (11)0.0359 (7)
C6C1.0989 (3)0.62355 (12)0.39452 (11)0.0438 (8)
O11D0.18351 (17)0.24154 (8)0.33582 (8)0.0468 (5)
O12D0.10205 (17)0.19402 (8)0.44197 (8)0.0525 (6)
O31D0.2163 (2)0.02162 (9)0.46941 (12)0.0719 (7)
O32D0.2969 (2)0.06595 (10)0.37460 (12)0.0894 (9)
O51D0.1722 (2)0.06064 (11)0.13729 (10)0.0937 (9)
O52D0.0215 (3)0.13759 (12)0.12532 (10)0.0942 (9)
N11D0.11084 (19)0.19562 (9)0.37591 (10)0.0356 (6)
N31D0.2226 (2)0.02208 (10)0.40421 (15)0.0568 (8)
N51D0.0715 (3)0.09712 (12)0.16134 (12)0.0623 (9)
C1D0.0261 (2)0.13858 (10)0.34367 (10)0.0278 (6)
C2D0.0500 (2)0.08493 (10)0.38886 (11)0.0320 (7)
C3D0.1353 (2)0.03493 (10)0.35704 (12)0.0364 (7)
C4D0.1457 (2)0.03741 (11)0.28337 (13)0.0434 (8)
C5D0.0634 (2)0.09174 (11)0.24105 (11)0.0381 (8)
C6D0.0245 (2)0.14302 (10)0.26951 (11)0.0331 (7)
O11E1.0370 (2)0.40646 (12)0.35729 (9)0.0855 (9)
O12E0.8341 (2)0.48221 (10)0.34813 (9)0.0778 (7)
O31E0.6554 (2)0.57439 (9)0.11041 (10)0.0728 (7)
O32E0.7634 (2)0.52991 (10)0.01659 (11)0.0872 (9)
O51E1.0834 (2)0.30715 (9)0.05044 (9)0.0807 (8)
O52E1.19387 (19)0.27635 (8)0.15271 (9)0.0590 (6)
N11E0.9344 (3)0.44178 (12)0.32300 (11)0.0538 (8)
N31E0.7460 (2)0.53190 (10)0.08200 (13)0.0551 (8)
N51E1.1046 (2)0.31519 (10)0.11382 (11)0.0497 (8)
C1E0.9312 (2)0.43540 (11)0.24451 (11)0.0363 (8)
C2E0.8385 (2)0.48504 (11)0.20222 (12)0.0398 (8)
C3E0.8420 (2)0.47900 (11)0.12899 (12)0.0382 (7)
C4E0.9293 (2)0.42476 (11)0.09874 (11)0.0397 (8)
C5E1.0170 (2)0.37599 (10)0.14410 (11)0.0352 (7)
C6E1.0227 (2)0.38071 (11)0.21716 (11)0.0366 (7)
H4X10.862000.818500.019900.0710*0.500
H4X20.854900.896200.001800.0710*0.500
H2A0.596100.714100.136000.0420*0.500
H2X0.539300.687700.148500.0420*0.500
H3A0.760100.773400.046100.0560*0.500
H3X0.713100.722200.053300.0560*0.500
H5A0.668400.964700.135500.0420*0.500
H5X0.709100.930900.105100.0420*0.500
H6A0.502000.905400.222700.0350*0.500
H6X0.534300.892200.206500.0350*0.500
H21A0.516700.829300.366000.0410*
H31A0.657800.788700.468200.0420*
H41A0.884200.892100.003300.0710*0.500
H42A0.841500.961600.031800.0710*0.500
H43A0.779000.687900.542300.0610*
H44A0.774800.609500.523000.0610*
H51A0.648900.580300.415800.0410*
H61A0.510600.621700.313000.0400*
H2B0.555600.329800.137600.0520*
H3B0.402300.435300.104900.0680*
H5B0.375500.477500.313400.0710*
H6B0.525800.371900.346000.0560*
H21B0.524400.166500.191100.0480*
H31B0.384100.059900.223000.0560*
H41B0.247600.558300.219000.1110*
H42B0.261300.542100.140400.1110*
H43B0.280200.029200.316900.0870*
H44B0.300700.021200.396600.0870*
H51B0.437900.081400.434300.0530*
H61B0.576700.188800.401600.0450*
H2F0.304400.943300.061500.0650*
H4F0.022200.777800.153000.0480*
H6F0.328500.746500.016300.0860*
H2C0.984300.793000.347200.0420*
H4C1.266000.713100.512500.0390*
H6C1.088600.575400.381400.0530*
H2D0.044100.082400.439900.0380*
H4D0.207100.003100.262400.0520*
H6D0.081300.179700.239500.0400*
H2E0.774700.521900.222600.0480*
H4E0.929200.421000.048300.0480*
H6E1.087200.347600.247300.0440*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0317 (3)0.0441 (3)0.0353 (3)0.0037 (3)0.0080 (2)0.0057 (3)
O1A0.0360 (8)0.0693 (11)0.0431 (9)0.0214 (8)0.0034 (7)0.0111 (8)
O11A0.0771 (11)0.0574 (11)0.0677 (11)0.0303 (9)0.0429 (9)0.0119 (9)
N4A0.0402 (14)0.088 (2)0.0441 (18)0.0020 (19)0.0090 (14)0.0093 (18)
N4X0.0402 (14)0.088 (2)0.0441 (18)0.0020 (19)0.0090 (14)0.0093 (18)
N41A0.0749 (13)0.0345 (11)0.0443 (12)0.0022 (9)0.0296 (10)0.0012 (9)
C1A0.0286 (11)0.0487 (14)0.0251 (12)0.0100 (10)0.0058 (9)0.0012 (11)
C2A0.042 (4)0.026 (4)0.0388 (18)0.008 (3)0.013 (2)0.010 (4)
C2X0.042 (4)0.026 (4)0.0388 (18)0.008 (3)0.013 (2)0.010 (4)
C3A0.045 (3)0.055 (4)0.036 (2)0.013 (3)0.0011 (19)0.007 (4)
C3X0.045 (3)0.055 (4)0.036 (2)0.013 (3)0.0011 (19)0.007 (4)
C4A0.0231 (16)0.057 (4)0.017 (2)0.009 (3)0.0010 (14)0.004 (3)
C4X0.0231 (16)0.057 (4)0.017 (2)0.009 (3)0.0010 (14)0.004 (3)
C5A0.032 (2)0.038 (3)0.034 (3)0.000 (3)0.005 (2)0.001 (2)
C5X0.032 (2)0.038 (3)0.034 (3)0.000 (3)0.005 (2)0.001 (2)
C6A0.031 (3)0.021 (6)0.037 (4)0.005 (3)0.004 (2)0.012 (3)
C6X0.031 (3)0.021 (6)0.037 (4)0.005 (3)0.004 (2)0.012 (3)
C11A0.0262 (10)0.0339 (12)0.0305 (12)0.0049 (9)0.0031 (9)0.0021 (9)
C21A0.0361 (11)0.0264 (11)0.0385 (13)0.0001 (9)0.0026 (10)0.0006 (10)
C31A0.0408 (12)0.0307 (12)0.0358 (13)0.0062 (9)0.0079 (10)0.0066 (10)
C41A0.0359 (11)0.0314 (12)0.0301 (12)0.0039 (9)0.0061 (9)0.0017 (10)
C51A0.0421 (12)0.0236 (11)0.0355 (12)0.0016 (9)0.0046 (10)0.0011 (9)
C61A0.0403 (12)0.0307 (12)0.0309 (12)0.0067 (9)0.0032 (10)0.0042 (9)
S1B0.0287 (3)0.0283 (3)0.0534 (4)0.0025 (2)0.0064 (3)0.0047 (3)
O1B0.0386 (8)0.0394 (9)0.0673 (11)0.0012 (7)0.0173 (8)0.0064 (8)
O11B0.0470 (9)0.0418 (9)0.0735 (11)0.0099 (7)0.0330 (8)0.0039 (8)
N4B0.0573 (13)0.0454 (13)0.167 (3)0.0159 (11)0.0117 (15)0.0187 (15)
N41B0.0598 (13)0.0407 (12)0.1129 (18)0.0171 (10)0.0085 (13)0.0056 (12)
C1B0.0284 (11)0.0272 (11)0.0472 (14)0.0048 (9)0.0046 (10)0.0004 (10)
C2B0.0406 (13)0.0365 (13)0.0530 (15)0.0021 (10)0.0102 (11)0.0014 (11)
C3B0.0477 (14)0.0428 (15)0.0765 (19)0.0083 (12)0.0264 (13)0.0156 (14)
C4B0.0311 (13)0.0288 (14)0.117 (2)0.0011 (10)0.0060 (15)0.0090 (16)
C5B0.0483 (15)0.0386 (15)0.091 (2)0.0009 (12)0.0087 (15)0.0125 (15)
C6B0.0446 (13)0.0387 (13)0.0566 (15)0.0033 (11)0.0002 (12)0.0045 (12)
C11B0.0266 (10)0.0258 (11)0.0372 (13)0.0007 (8)0.0027 (9)0.0015 (9)
C21B0.0397 (12)0.0441 (14)0.0351 (13)0.0032 (10)0.0015 (10)0.0032 (11)
C31B0.0389 (13)0.0416 (14)0.0614 (17)0.0077 (11)0.0060 (12)0.0145 (12)
C41B0.0285 (12)0.0282 (13)0.0757 (18)0.0014 (9)0.0062 (12)0.0017 (12)
C51B0.0425 (13)0.0409 (14)0.0431 (14)0.0044 (11)0.0070 (11)0.0143 (11)
C61B0.0352 (12)0.0359 (12)0.0400 (14)0.0028 (10)0.0054 (10)0.0029 (10)
O11'0.092 (2)0.117 (5)0.0410 (14)0.002 (4)0.0015 (14)0.012 (3)
O11F0.092 (2)0.117 (5)0.0410 (14)0.002 (4)0.0015 (14)0.012 (3)
O12'0.0806 (17)0.071 (4)0.077 (3)0.038 (4)0.0293 (18)0.029 (3)
O12F0.0806 (17)0.071 (4)0.077 (3)0.038 (4)0.0293 (18)0.029 (3)
O31F0.0742 (13)0.0491 (12)0.166 (2)0.0032 (10)0.0150 (13)0.0486 (13)
O32F0.0468 (10)0.0728 (13)0.0723 (13)0.0154 (9)0.0068 (9)0.0275 (10)
O51'0.087 (7)0.0425 (14)0.063 (5)0.020 (4)0.001 (4)0.001 (3)
O51F0.087 (7)0.0425 (14)0.063 (5)0.020 (4)0.001 (4)0.001 (3)
O52'0.100 (5)0.037 (3)0.086 (5)0.014 (2)0.023 (3)0.025 (3)
O52F0.100 (5)0.037 (3)0.086 (5)0.014 (2)0.023 (3)0.025 (3)
N11'0.061 (2)0.076 (7)0.039 (2)0.016 (5)0.0221 (17)0.010 (5)
N11F0.061 (2)0.076 (7)0.039 (2)0.016 (5)0.0221 (17)0.010 (5)
N31F0.0421 (12)0.0469 (14)0.0826 (17)0.0120 (11)0.0209 (12)0.0223 (12)
N51F0.122 (3)0.054 (2)0.078 (2)0.0342 (18)0.0631 (19)0.0293 (16)
C1F0.0444 (16)0.136 (3)0.0282 (15)0.0172 (19)0.0141 (13)0.0013 (18)
C2F0.0412 (14)0.0636 (17)0.0546 (17)0.0026 (12)0.0251 (13)0.0140 (14)
C3F0.0346 (12)0.0406 (14)0.0462 (14)0.0096 (10)0.0202 (11)0.0107 (12)
C4F0.0399 (12)0.0386 (13)0.0430 (14)0.0068 (10)0.0203 (11)0.0066 (11)
C5F0.0685 (17)0.0486 (16)0.0443 (16)0.0230 (13)0.0310 (14)0.0176 (13)
C6F0.072 (2)0.111 (3)0.0376 (17)0.0429 (19)0.0265 (15)0.0292 (18)
O11C0.178 (2)0.0708 (14)0.0599 (13)0.0583 (14)0.0368 (13)0.0059 (11)
O12C0.0562 (11)0.1047 (16)0.0502 (11)0.0182 (10)0.0188 (9)0.0135 (11)
O31C0.0645 (10)0.0328 (9)0.0648 (11)0.0111 (8)0.0039 (9)0.0032 (8)
O32C0.0604 (10)0.0449 (10)0.0633 (11)0.0057 (8)0.0109 (9)0.0212 (8)
O51C0.0649 (11)0.0585 (11)0.0499 (11)0.0078 (9)0.0064 (9)0.0120 (9)
O52C0.173 (2)0.0268 (10)0.0910 (15)0.0110 (11)0.0330 (14)0.0085 (10)
N11C0.0445 (11)0.0305 (11)0.0418 (11)0.0008 (9)0.0080 (9)0.0044 (9)
N31C0.0719 (15)0.0686 (16)0.0441 (14)0.0408 (13)0.0111 (11)0.0057 (12)
N51C0.0752 (15)0.0358 (13)0.0414 (12)0.0049 (11)0.0045 (11)0.0050 (10)
C1C0.0437 (13)0.0448 (14)0.0305 (12)0.0210 (10)0.0024 (10)0.0001 (11)
C2C0.0304 (11)0.0382 (13)0.0354 (13)0.0054 (9)0.0026 (10)0.0041 (10)
C3C0.0300 (11)0.0276 (11)0.0322 (12)0.0015 (9)0.0050 (9)0.0033 (9)
C4C0.0343 (11)0.0351 (12)0.0294 (12)0.0054 (9)0.0021 (9)0.0048 (10)
C5C0.0479 (13)0.0273 (12)0.0310 (12)0.0028 (10)0.0038 (10)0.0019 (10)
C6C0.0640 (15)0.0316 (13)0.0361 (13)0.0164 (11)0.0023 (12)0.0028 (10)
O11D0.0498 (9)0.0346 (9)0.0554 (10)0.0139 (7)0.0074 (8)0.0036 (8)
O12D0.0627 (10)0.0622 (11)0.0361 (10)0.0180 (8)0.0029 (8)0.0162 (8)
O31D0.0836 (13)0.0421 (10)0.0847 (14)0.0051 (9)0.0331 (12)0.0034 (10)
O32D0.0762 (13)0.0443 (11)0.1481 (19)0.0303 (10)0.0290 (13)0.0046 (12)
O51D0.1170 (16)0.0956 (15)0.0795 (14)0.0097 (13)0.0617 (13)0.0396 (12)
O52D0.167 (2)0.0766 (15)0.0412 (12)0.0144 (14)0.0097 (13)0.0116 (11)
N11D0.0350 (10)0.0310 (10)0.0419 (12)0.0001 (8)0.0061 (9)0.0076 (9)
N31D0.0420 (12)0.0291 (12)0.0970 (19)0.0020 (9)0.0048 (13)0.0001 (13)
N51D0.0900 (18)0.0486 (14)0.0531 (16)0.0211 (13)0.0313 (14)0.0218 (12)
C1D0.0257 (10)0.0242 (11)0.0346 (12)0.0019 (8)0.0034 (9)0.0083 (9)
C2D0.0333 (11)0.0260 (11)0.0367 (12)0.0059 (9)0.0010 (10)0.0060 (10)
C3D0.0293 (11)0.0216 (11)0.0589 (16)0.0030 (9)0.0002 (11)0.0083 (10)
C4D0.0388 (12)0.0270 (12)0.0692 (18)0.0083 (10)0.0229 (12)0.0210 (12)
C5D0.0473 (13)0.0307 (12)0.0391 (14)0.0115 (10)0.0170 (11)0.0137 (11)
C6D0.0336 (11)0.0271 (11)0.0385 (13)0.0082 (9)0.0045 (10)0.0051 (10)
O11E0.0944 (15)0.1181 (17)0.0475 (12)0.0032 (13)0.0249 (11)0.0178 (11)
O12E0.1133 (15)0.0687 (12)0.0515 (11)0.0099 (11)0.0321 (11)0.0192 (10)
O31E0.0678 (12)0.0477 (11)0.1024 (15)0.0130 (9)0.0069 (11)0.0086 (10)
O32E0.1282 (17)0.0727 (14)0.0597 (13)0.0223 (12)0.0317 (12)0.0008 (11)
O51E0.1281 (16)0.0698 (13)0.0460 (11)0.0309 (11)0.0065 (11)0.0224 (10)
O52E0.0651 (11)0.0416 (10)0.0708 (12)0.0081 (8)0.0112 (9)0.0083 (9)
N11E0.0673 (15)0.0548 (14)0.0414 (13)0.0252 (11)0.0085 (12)0.0122 (11)
N31E0.0619 (14)0.0349 (12)0.0694 (16)0.0041 (10)0.0147 (12)0.0045 (12)
N51E0.0656 (14)0.0366 (12)0.0473 (14)0.0010 (10)0.0013 (11)0.0075 (10)
C1E0.0423 (13)0.0357 (13)0.0327 (13)0.0170 (10)0.0026 (10)0.0085 (10)
C2E0.0357 (12)0.0342 (13)0.0519 (15)0.0119 (10)0.0052 (11)0.0152 (11)
C3E0.0413 (12)0.0288 (12)0.0456 (14)0.0059 (10)0.0070 (11)0.0053 (11)
C4E0.0534 (14)0.0349 (13)0.0321 (12)0.0082 (11)0.0017 (11)0.0073 (10)
C5E0.0423 (12)0.0254 (11)0.0387 (13)0.0059 (9)0.0002 (10)0.0061 (10)
C6E0.0387 (12)0.0350 (12)0.0361 (13)0.0146 (10)0.0038 (10)0.0005 (10)
Geometric parameters (Å, º) top
S1A—O1A1.4417 (15)N11E—C1E1.481 (3)
S1A—O11A1.4405 (16)C21A—C31A1.376 (3)
S1A—C1A1.7456 (19)C31A—C41A1.395 (3)
S1A—C11A1.7494 (19)N31E—C3E1.473 (3)
S1B—C1B1.7543 (19)C41A—C51A1.404 (3)
S1B—O1B1.4464 (15)C51A—C61A1.375 (3)
S1B—O11B1.4413 (15)N51E—C5E1.466 (3)
S1B—C11B1.7566 (19)C2A—H2A0.9500
O11'—N11'1.237 (10)C2X—H2X0.9500
O11F—N11F1.239 (11)C3A—H3A0.9500
O12'—N11'1.177 (9)C3X—H3X0.9500
O12F—N11F1.256 (9)C5A—H5A0.9500
O31F—N31F1.224 (3)C5X—H5X0.9500
O32F—N31F1.211 (3)C6A—H6A0.9500
O51'—N51F1.523 (10)C6X—H6X0.9500
O51F—N51F0.926 (10)C21A—H21A0.9500
O52'—N51F1.155 (8)C31A—H31A0.9500
O52F—N51F1.382 (8)C51A—H51A0.9500
O11C—N31C1.224 (3)C61A—H61A0.9500
O12C—N31C1.215 (3)C1B—C6B1.388 (3)
O31C—N11C1.222 (2)C1B—C2B1.378 (3)
O32C—N11C1.218 (2)C2B—C3B1.377 (3)
O51C—N51C1.208 (3)C3B—C4B1.392 (4)
O52C—N51C1.211 (3)C4B—C5B1.383 (4)
O11D—N11D1.219 (2)C5B—C6B1.369 (3)
O12D—N11D1.227 (2)C11B—C61B1.378 (3)
O31D—N31D1.219 (4)C11B—C21B1.386 (3)
O32D—N31D1.222 (3)C21B—C31B1.374 (3)
O51D—N51D1.219 (3)C31B—C41B1.384 (3)
O52D—N51D1.217 (3)C41B—C51B1.396 (3)
N4A—C4A1.397 (6)C51B—C61B1.380 (3)
N4X—C4X1.385 (7)C2B—H2B0.9500
O11E—N11E1.215 (3)C3B—H3B0.9500
O12E—N11E1.213 (3)C5B—H5B0.9500
O31E—N31E1.216 (3)C6B—H6B0.9500
O32E—N31E1.225 (3)C21B—H21B0.9500
N41A—C41A1.361 (2)C31B—H31B0.9500
O51E—N51E1.227 (3)C51B—H51B0.9500
O52E—N51E1.218 (2)C61B—H61B0.9500
N4A—H42A0.8800C1F—C2F1.362 (4)
N4A—H41A0.8800C1F—C6F1.360 (5)
N4X—H4X20.8800C2F—C3F1.382 (3)
N4X—H4X10.8800C3F—C4F1.373 (3)
N41A—H43A0.8800C4F—C5F1.365 (3)
N41A—H44A0.8800C5F—C6F1.368 (4)
N4B—C4B1.385 (3)C2F—H2F0.9500
N41B—C41B1.380 (3)C4F—H4F0.9500
N4B—H42B0.8800C6F—H6F0.9500
N4B—H41B0.8800C1C—C6C1.370 (3)
N41B—H44B0.8800C1C—C2C1.364 (3)
N41B—H43B0.8800C2C—C3C1.374 (3)
N11'—C1F1.485 (10)C3C—C4C1.376 (3)
N11F—C1F1.604 (10)C4C—C5C1.368 (3)
N31F—C3F1.475 (3)C5C—C6C1.380 (3)
N51F—C5F1.471 (4)C2C—H2C0.9500
N11C—C3C1.473 (2)C4C—H4C0.9500
N31C—C1C1.477 (3)C6C—H6C0.9500
N51C—C5C1.476 (3)C1D—C2D1.373 (3)
N11D—C1D1.475 (2)C1D—C6D1.375 (3)
N31D—C3D1.477 (3)C2D—C3D1.377 (3)
N51D—C5D1.481 (3)C3D—C4D1.374 (3)
C1A—C6A1.563 (11)C4D—C5D1.380 (3)
C1A—C2X1.506 (8)C5D—C6D1.374 (3)
C1A—C2A1.296 (10)C2D—H2D0.9500
C1A—C6X1.208 (12)C4D—H4D0.9500
C2A—C3A1.401 (13)C6D—H6D0.9500
C2X—C3X1.325 (13)C1E—C2E1.376 (3)
C3A—C4A1.378 (9)C1E—C6E1.371 (3)
C3X—C4X1.355 (9)C2E—C3E1.380 (3)
C4A—C5A1.438 (8)C3E—C4E1.372 (3)
C4X—C5X1.422 (9)C4E—C5E1.375 (3)
C5A—C6A1.339 (15)C5E—C6E1.376 (3)
C5X—C6X1.432 (14)C2E—H2E0.9500
C11A—C21A1.388 (3)C4E—H4E0.9500
C11A—C61A1.382 (3)C6E—H6E0.9500
O1A—S1A—O11A118.15 (9)C21A—C31A—H31A120.00
O1A—S1A—C1A106.20 (9)C41A—C31A—H31A120.00
O1A—S1A—C11A107.65 (9)C41A—C51A—H51A120.00
O11A—S1A—C1A108.53 (10)C61A—C51A—H51A120.00
O11A—S1A—C11A107.83 (9)C11A—C61A—H61A120.00
C1A—S1A—C11A108.13 (8)C51A—C61A—H61A120.00
O1B—S1B—O11B118.73 (8)S1B—C1B—C2B120.05 (15)
O1B—S1B—C1B106.63 (9)S1B—C1B—C6B120.34 (16)
O1B—S1B—C11B106.91 (9)C2B—C1B—C6B119.51 (18)
O11B—S1B—C1B107.67 (9)C1B—C2B—C3B120.5 (2)
O11B—S1B—C11B107.47 (9)C2B—C3B—C4B120.1 (2)
C1B—S1B—C11B109.20 (8)N4B—C4B—C5B121.4 (3)
C4A—N4A—H42A120.00N4B—C4B—C3B119.6 (3)
H41A—N4A—H42A120.00C3B—C4B—C5B118.9 (2)
C4A—N4A—H41A120.00C4B—C5B—C6B121.0 (2)
C4X—N4X—H4X1120.00C1B—C6B—C5B120.0 (2)
C4X—N4X—H4X2120.00S1B—C11B—C21B119.53 (15)
H4X1—N4X—H4X2120.00C21B—C11B—C61B119.31 (17)
C41A—N41A—H43A120.00S1B—C11B—C61B121.05 (15)
H43A—N41A—H44A120.00C11B—C21B—C31B120.49 (19)
C41A—N41A—H44A120.00C21B—C31B—C41B120.6 (2)
H41B—N4B—H42B120.00N41B—C41B—C51B120.5 (2)
C4B—N4B—H42B120.00C31B—C41B—C51B118.88 (19)
C4B—N4B—H41B120.00N41B—C41B—C31B120.7 (2)
C41B—N41B—H43B120.00C41B—C51B—C61B120.2 (2)
C41B—N41B—H44B120.00C11B—C61B—C51B120.52 (19)
H43B—N41B—H44B120.00C3B—C2B—H2B120.00
O11'—N11'—O12'133.5 (10)C1B—C2B—H2B120.00
O11'—N11'—C1F121.8 (7)C2B—C3B—H3B120.00
O12'—N11'—C1F104.7 (7)C4B—C3B—H3B120.00
O12F—N11F—C1F125.6 (7)C6B—C5B—H5B119.00
O11F—N11F—O12F124.3 (9)C4B—C5B—H5B120.00
O11F—N11F—C1F110.1 (6)C5B—C6B—H6B120.00
O31F—N31F—O32F124.4 (2)C1B—C6B—H6B120.00
O32F—N31F—C3F118.24 (18)C11B—C21B—H21B120.00
O31F—N31F—C3F117.33 (19)C31B—C21B—H21B120.00
O51F—N51F—C5F121.1 (7)C21B—C31B—H31B120.00
O51'—N51F—O52'109.4 (6)C41B—C31B—H31B120.00
O52F—N51F—C5F103.0 (4)C61B—C51B—H51B120.00
O52'—N51F—C5F135.4 (5)C41B—C51B—H51B120.00
O51'—N51F—C5F115.0 (5)C11B—C61B—H61B120.00
O51F—N51F—O52F135.9 (8)C51B—C61B—H61B120.00
O31C—N11C—O32C123.96 (17)N11'—C1F—C6F105.3 (4)
O31C—N11C—C3C118.02 (16)N11F—C1F—C6F131.2 (4)
O32C—N11C—C3C118.01 (16)C2F—C1F—C6F122.8 (2)
O11C—N31C—C1C116.3 (2)N11'—C1F—C2F131.8 (4)
O11C—N31C—O12C125.8 (2)N11F—C1F—C2F106.1 (4)
O12C—N31C—C1C117.9 (2)C1F—C2F—C3F116.9 (2)
O51C—N51C—C5C118.15 (19)N31F—C3F—C4F118.23 (18)
O51C—N51C—O52C124.4 (2)C2F—C3F—C4F123.3 (2)
O52C—N51C—C5C117.4 (2)N31F—C3F—C2F118.5 (2)
O11D—N11D—O12D124.08 (17)C3F—C4F—C5F116.01 (19)
O11D—N11D—C1D118.57 (17)N51F—C5F—C6F117.7 (3)
O12D—N11D—C1D117.35 (16)C4F—C5F—C6F123.5 (2)
O32D—N31D—C3D117.2 (2)N51F—C5F—C4F118.7 (2)
O31D—N31D—O32D125.0 (2)C1F—C6F—C5F117.6 (3)
O31D—N31D—C3D117.86 (18)C1F—C2F—H2F122.00
O51D—N51D—O52D125.4 (2)C3F—C2F—H2F122.00
O51D—N51D—C5D116.9 (2)C3F—C4F—H4F122.00
O52D—N51D—C5D117.8 (2)C5F—C4F—H4F122.00
S1A—C1A—C6X127.0 (6)C5F—C6F—H6F121.00
C2A—C1A—C6A114.2 (6)C1F—C6F—H6F121.00
S1A—C1A—C2X110.2 (4)C2C—C1C—C6C123.08 (19)
S1A—C1A—C2A132.7 (4)N31C—C1C—C2C117.67 (19)
C2X—C1A—C6X122.8 (7)N31C—C1C—C6C119.1 (2)
S1A—C1A—C6A113.1 (5)C1C—C2C—C3C116.67 (18)
C1A—C2A—C3A127.5 (5)N11C—C3C—C4C118.63 (16)
C1A—C2X—C3X115.2 (5)N11C—C3C—C2C117.75 (17)
C2A—C3A—C4A118.1 (6)C2C—C3C—C4C123.44 (18)
C2X—C3X—C4X123.4 (6)C3C—C4C—C5C116.95 (17)
N4A—C4A—C5A117.0 (5)C4C—C5C—C6C122.29 (19)
N4A—C4A—C3A123.0 (5)N51C—C5C—C6C118.22 (19)
C3A—C4A—C5A120.0 (5)N51C—C5C—C4C119.38 (17)
C3X—C4X—C5X119.9 (5)C1C—C6C—C5C117.6 (2)
N4X—C4X—C3X123.6 (6)C1C—C2C—H2C122.00
N4X—C4X—C5X116.6 (6)C3C—C2C—H2C122.00
C4A—C5A—C6A120.6 (7)C5C—C4C—H4C121.00
C4X—C5X—C6X116.2 (6)C3C—C4C—H4C122.00
C1A—C6A—C5A119.6 (10)C5C—C6C—H6C121.00
C1A—C6X—C5X122.6 (10)C1C—C6C—H6C121.00
S1A—C11A—C21A119.15 (14)C2D—C1D—C6D123.37 (17)
C21A—C11A—C61A120.05 (17)N11D—C1D—C2D118.66 (17)
S1A—C11A—C61A120.79 (14)N11D—C1D—C6D117.95 (16)
O12E—N11E—C1E117.2 (2)C1D—C2D—C3D117.14 (19)
O11E—N11E—O12E125.0 (2)N31D—C3D—C4D119.01 (18)
O11E—N11E—C1E117.8 (2)C2D—C3D—C4D122.50 (18)
C11A—C21A—C31A119.96 (18)N31D—C3D—C2D118.5 (2)
C21A—C31A—C41A120.87 (18)C3D—C4D—C5D117.37 (18)
O32E—N31E—C3E117.32 (18)N51D—C5D—C4D119.52 (19)
O31E—N31E—O32E124.5 (2)N51D—C5D—C6D117.56 (18)
O31E—N31E—C3E118.2 (2)C4D—C5D—C6D122.91 (19)
C31A—C41A—C51A118.35 (16)C1D—C6D—C5D116.67 (17)
N41A—C41A—C51A120.82 (17)C3D—C2D—H2D121.00
N41A—C41A—C31A120.82 (17)C1D—C2D—H2D121.00
C41A—C51A—C61A120.65 (17)C3D—C4D—H4D121.00
O52E—N51E—C5E118.28 (18)C5D—C4D—H4D121.00
O51E—N51E—O52E124.29 (19)C5D—C6D—H6D122.00
O51E—N51E—C5E117.44 (17)C1D—C6D—H6D122.00
C11A—C61A—C51A120.11 (18)N11E—C1E—C2E118.68 (18)
C1A—C2A—H2A116.00N11E—C1E—C6E118.33 (18)
C3A—C2A—H2A116.00C2E—C1E—C6E122.98 (19)
C1A—C2X—H2X122.00C1E—C2E—C3E117.25 (18)
C3X—C2X—H2X122.00N31E—C3E—C2E118.68 (18)
C4A—C3A—H3A121.00N31E—C3E—C4E118.98 (19)
C2A—C3A—H3A121.00C2E—C3E—C4E122.33 (19)
C4X—C3X—H3X118.00C3E—C4E—C5E117.58 (19)
C2X—C3X—H3X118.00N51E—C5E—C4E118.71 (18)
C6A—C5A—H5A120.00N51E—C5E—C6E118.52 (17)
C4A—C5A—H5A120.00C4E—C5E—C6E122.76 (18)
C4X—C5X—H5X122.00C1E—C6E—C5E117.04 (18)
C6X—C5X—H5X122.00C1E—C2E—H2E121.00
C5A—C6A—H6A120.00C3E—C2E—H2E121.00
C1A—C6A—H6A120.00C3E—C4E—H4E121.00
C5X—C6X—H6X119.00C5E—C4E—H4E121.00
C1A—C6X—H6X119.00C1E—C6E—H6E121.00
C11A—C21A—H21A120.00C5E—C6E—H6E121.00
C31A—C21A—H21A120.00
O1A—S1A—C1A—C2A156.7 (6)C21A—C31A—C41A—N41A179.94 (17)
O1A—S1A—C1A—C6A24.6 (6)O32E—N31E—C3E—C2E173.00 (18)
O11A—S1A—C1A—C2A28.7 (7)O31E—N31E—C3E—C2E7.0 (3)
O11A—S1A—C1A—C6A152.5 (6)O31E—N31E—C3E—C4E171.87 (18)
C11A—S1A—C1A—C2A88.0 (6)O32E—N31E—C3E—C4E8.2 (3)
C11A—S1A—C1A—C6A90.8 (6)N41A—C41A—C51A—C61A179.49 (17)
O1A—S1A—C11A—C21A31.97 (17)C31A—C41A—C51A—C61A0.3 (3)
O1A—S1A—C11A—C61A147.63 (14)C41A—C51A—C61A—C11A0.7 (3)
O11A—S1A—C11A—C21A160.46 (15)O52E—N51E—C5E—C6E8.5 (3)
O11A—S1A—C11A—C61A19.14 (18)O51E—N51E—C5E—C6E171.95 (17)
C1A—S1A—C11A—C21A82.38 (17)O51E—N51E—C5E—C4E6.4 (3)
C1A—S1A—C11A—C61A98.03 (16)O52E—N51E—C5E—C4E173.22 (17)
C1B—S1B—C11B—C61B101.70 (16)C2B—C1B—C6B—C5B1.0 (3)
O11B—S1B—C1B—C6B26.78 (17)S1B—C1B—C2B—C3B175.63 (16)
C11B—S1B—C1B—C2B94.11 (16)C6B—C1B—C2B—C3B0.7 (3)
C11B—S1B—C1B—C6B89.61 (17)S1B—C1B—C6B—C5B175.26 (16)
O1B—S1B—C11B—C21B32.92 (17)C1B—C2B—C3B—C4B0.4 (3)
O1B—S1B—C1B—C2B21.07 (17)C2B—C3B—C4B—C5B1.1 (4)
O1B—S1B—C1B—C6B155.22 (15)C2B—C3B—C4B—N4B179.6 (2)
O11B—S1B—C1B—C2B149.51 (15)N4B—C4B—C5B—C6B179.3 (2)
C1B—S1B—C11B—C21B82.08 (17)C3B—C4B—C5B—C6B0.8 (4)
O1B—S1B—C11B—C61B143.30 (15)C4B—C5B—C6B—C1B0.3 (3)
O11B—S1B—C11B—C21B161.40 (14)C61B—C11B—C21B—C31B0.8 (3)
O11B—S1B—C11B—C61B14.82 (17)S1B—C11B—C21B—C31B175.52 (14)
O11F—N11F—C1F—C6F12.2 (10)S1B—C11B—C61B—C51B175.17 (14)
O12F—N11F—C1F—C2F10.0 (10)C21B—C11B—C61B—C51B1.1 (3)
O12F—N11F—C1F—C6F171.1 (7)C11B—C21B—C31B—C41B0.3 (3)
O11F—N11F—C1F—C2F166.7 (6)C21B—C31B—C41B—N41B179.27 (17)
O31F—N31F—C3F—C2F7.6 (3)C21B—C31B—C41B—C51B1.1 (3)
O31F—N31F—C3F—C4F170.44 (19)C31B—C41B—C51B—C61B0.8 (3)
O32F—N31F—C3F—C2F173.1 (2)N41B—C41B—C51B—C61B179.56 (17)
O32F—N31F—C3F—C4F8.8 (3)C41B—C51B—C61B—C11B0.3 (3)
O51F—N51F—C5F—C6F166.6 (8)N11F—C1F—C6F—C5F180.0 (5)
O51F—N51F—C5F—C4F15.6 (9)C6F—C1F—C2F—C3F1.2 (4)
O52F—N51F—C5F—C4F166.0 (4)N11F—C1F—C2F—C3F179.7 (4)
O52F—N51F—C5F—C6F11.8 (5)C2F—C1F—C6F—C5F1.3 (4)
O32C—N11C—C3C—C2C165.13 (18)C1F—C2F—C3F—N31F177.5 (2)
O31C—N11C—C3C—C4C170.91 (17)C1F—C2F—C3F—C4F0.5 (3)
O32C—N11C—C3C—C4C10.1 (3)C2F—C3F—C4F—C5F2.1 (3)
O31C—N11C—C3C—C2C13.9 (3)N31F—C3F—C4F—C5F175.89 (19)
O11C—N31C—C1C—C6C8.4 (3)C3F—C4F—C5F—N51F175.7 (2)
O11C—N31C—C1C—C2C167.5 (2)C3F—C4F—C5F—C6F2.1 (3)
O12C—N31C—C1C—C2C11.2 (3)C4F—C5F—C6F—C1F0.5 (4)
O12C—N31C—C1C—C6C172.9 (2)N51F—C5F—C6F—C1F177.3 (3)
O51C—N51C—C5C—C4C3.4 (3)C2C—C1C—C6C—C5C0.8 (3)
O51C—N51C—C5C—C6C172.9 (2)C6C—C1C—C2C—C3C1.4 (3)
O52C—N51C—C5C—C6C5.0 (3)N31C—C1C—C6C—C5C174.94 (19)
O52C—N51C—C5C—C4C178.8 (2)N31C—C1C—C2C—C3C174.40 (18)
O12D—N11D—C1D—C2D3.5 (2)C1C—C2C—C3C—N11C174.02 (16)
O11D—N11D—C1D—C2D177.22 (16)C1C—C2C—C3C—C4C1.0 (3)
O12D—N11D—C1D—C6D175.08 (16)C2C—C3C—C4C—C5C0.0 (3)
O11D—N11D—C1D—C6D4.3 (2)N11C—C3C—C4C—C5C174.94 (16)
O31D—N31D—C3D—C2D0.8 (3)C3C—C4C—C5C—C6C0.7 (3)
O32D—N31D—C3D—C2D179.74 (17)C3C—C4C—C5C—N51C176.74 (17)
O31D—N31D—C3D—C4D177.44 (18)C4C—C5C—C6C—C1C0.3 (3)
O32D—N31D—C3D—C4D2.0 (3)N51C—C5C—C6C—C1C176.43 (19)
O51D—N51D—C5D—C6D166.8 (2)C6D—C1D—C2D—C3D1.9 (3)
O52D—N51D—C5D—C6D12.8 (3)N11D—C1D—C6D—C5D176.21 (16)
O52D—N51D—C5D—C4D168.6 (2)C2D—C1D—C6D—C5D2.3 (3)
O51D—N51D—C5D—C4D11.8 (3)N11D—C1D—C2D—C3D176.53 (16)
S1A—C1A—C2A—C3A177.5 (6)C1D—C2D—C3D—N31D178.16 (16)
C2A—C1A—C6A—C5A2.8 (14)C1D—C2D—C3D—C4D0.0 (3)
S1A—C1A—C6A—C5A178.2 (8)N31D—C3D—C4D—C5D179.57 (16)
C6A—C1A—C2A—C3A3.8 (13)C2D—C3D—C4D—C5D1.4 (3)
C1A—C2A—C3A—C4A2.2 (14)C3D—C4D—C5D—N51D179.61 (18)
C2A—C3A—C4A—C5A0.8 (10)C3D—C4D—C5D—C6D1.1 (3)
C2A—C3A—C4A—N4A178.6 (7)C4D—C5D—C6D—C1D0.7 (3)
C3A—C4A—C5A—C6A1.5 (11)N51D—C5D—C6D—C1D177.89 (17)
N4A—C4A—C5A—C6A179.4 (8)N11E—C1E—C2E—C3E178.05 (18)
C4A—C5A—C6A—C1A0.3 (14)C6E—C1E—C2E—C3E1.1 (3)
S1A—C11A—C61A—C51A178.27 (14)N11E—C1E—C6E—C5E179.83 (18)
S1A—C11A—C21A—C31A178.72 (14)C2E—C1E—C6E—C5E1.1 (3)
C61A—C11A—C21A—C31A0.9 (3)C1E—C2E—C3E—N31E179.14 (16)
C21A—C11A—C61A—C51A1.3 (3)C1E—C2E—C3E—C4E2.1 (3)
O11E—N11E—C1E—C2E167.3 (2)N31E—C3E—C4E—C5E179.66 (16)
O12E—N11E—C1E—C2E12.5 (3)C2E—C3E—C4E—C5E0.9 (3)
O12E—N11E—C1E—C6E168.3 (2)C3E—C4E—C5E—N51E176.83 (16)
O11E—N11E—C1E—C6E11.8 (3)C3E—C4E—C5E—C6E1.4 (3)
C11A—C21A—C31A—C41A0.2 (3)N51E—C5E—C6E—C1E175.91 (16)
C21A—C31A—C41A—C51A0.8 (3)C4E—C5E—C6E—C1E2.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H41A···O52Di0.882.493.324 (4)160
N41A—H43A···O12Dii0.882.463.248 (2)149
N41A—H44A···O52Ciii0.882.263.096 (2)158
N41B—H44B···O31Civ0.882.583.028 (2)113
N4X—H4X1···O51Ev0.882.463.267 (4)152
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x1, y1, z; (v) x+2, y+1, z.

Experimental details

Crystal data
Chemical formulaC12H12N2O2S·2C6H3N3O6
Mr674.52
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)8.3196 (2), 18.3524 (5), 18.6285 (5)
α, β, γ (°)83.577 (2), 87.539 (2), 88.237 (2)
V3)2822.86 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.35 × 0.15 × 0.10
Data collection
DiffractometerOxford Diffraction Gemini-S Ultra CCD detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.932, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
34593, 11078, 6613
Rint0.041
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.077, 0.94
No. of reflections11078
No. of parameters880
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.28

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H41A···O52Di0.882.493.324 (4)160
N41A—H43A···O12Dii0.882.463.248 (2)149
N41A—H44A···O52Ciii0.882.263.096 (2)158
N4X—H4X1···O51Eiv0.882.463.267 (4)152
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x+2, y+1, z.
 

Acknowledgements

The authors acknowledge financial support from the Australian Research Committee and the University Library and the Faculty of Science and Technology, Queensland University of Technology.

References

First citationDickenson, C., Stewart, J. M. & Ammon, H. L. (1970). J. Chem. Soc. Chem. Commun. pp. 920–921.  Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationKus'mina, L. G., Struchkov, Yu. T., Novozhilova, N. V. & Tudorovskaya, G. L. (1981). Kristallografiya, 26, 690–694.  Google Scholar
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSmith, G., Wermuth, U. D. & White, J. M. (2002). Acta Cryst. E58, o1130–o1132.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWilson, J. D., Braunwald, E., Isselbacher, K. J., Petersdorf, R. G., Martin, J. B., Fauci, A. S. & Root, R. K. (1991). Harrison's Principles of Internal Medicine 12th ed., pp. 320, 647–648, 787. New York: McGraw-Hill.  Google Scholar

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