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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o795-o796
https://doi.org/10.1107/S1600536814013270

Ethyl 6-amino-5-cyano-4-phenyl-2,4-di­hydro­pyrano[2,3-c]pyrazole-3-carboxyl­ate di­methyl sulfoxide monosolvate

Naresh Sharma,a Goutam Brahmachari,b Bubun Banerjee,b Rajni Kanta and Vivek K. Guptaa*

aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bLaboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati University, Santiniketan 731 235, West Bengal, India
*Correspondence e-mail: vivek_gupta2k2@hotmail.com

(Received 28 May 2014; accepted 6 June 2014; online 18 June 2014)

In the asymmetric unit of the title compound, C16H14N4O3·C2H6OS, there are two independent main mol­ecules (A and B) and two dimethyl sulfoxide solvent mol­ecules. In mol­ecule A, the pyran ring is in a flattened sofa conformation, with the sp3-hydridized C atom forming the flap. In mol­ecule B, the pyran ring is in a flattened boat conformation, with the sp3-hydridized C atom and the O atom deviating by 0.073 (3) and 0.055 (3) Å, respectively, from the plane of the other four atoms. The mean planes the pyrazole and phenyl rings form dihedral angles of 84.4 (2) and 84.9 (2)°, respectively, for mol­ecules A and B. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link the components of the structure into chains along [010]. In both solvent mol­ecules, the S atoms are disordered over two sites, with occupancy ratios of 0.679 (4):0.321 (4) and 0.546 (6):0.454 (6).

CCDC reference: 1006444

Related literature

For background to the biological activity of synthetic pyrano[2,3-c] pyrazole compounds, see: Nasr et al. (2002[Nasr, M. N. & Gineinah, M. M. (2002). Arch. Pharm. Med. Chem. 335, 289-295.]); Ismail et al. (2003[Ismail, Z. H., Aly, G. M., El-Degwi, M. S., Heiba, H. I. & Ghorab, M. M. (2003). Egypt. J. Biotech. 13, 73-82.]); Foloppe et al. (2006[Foloppe, N., Fisher, L. M., Howes, R., Potter, A., Robertson, A. G. S. & Surgenor, A. E. (2006). Bioorg. Med. Chem. 14, 4792-4802.]); Mohamed et al. (2010[Mohamed, N. R., Khaireldin, N. Y., Fahmy, A. F. & El-Sayed, A. A. (2010). Der. Pharma Chem. 2, 400-417.]); Zonouz et al. (2012[Zonouz, A. M., Eskandari, I. & Khavasi, H. R. (2012). Tetrahedron Lett. 53, 5519-5522.]); Kuo et al. (1984[Kuo, S. C., Huang, L. J. & Nakamura, H. (1984). J. Med. Chem. 27, 539-544.]); Zaki et al. (2006[Zaki, M. E. A., Soliman, H. A., Hiekal, O. A. & Rashad, A. E. (2006). Z. Naturforsch. Teil C, 61, 1-5.]); Ahluwalia et al. (1997[Ahluwalia, V. K., Dahiya, A. & Garg, V. (1997). Indian J. Chem. Sect. B, 36, 88-91.]); Bhavanarushi et al. (2013[Bhavanarushi, S., Kanakaiah, V., Yakaiah, E., Saddanapu, V., Addlagatta, A. & Rani, V. J. (2013). Med. Chem. Res. 22, 2446-2454.]). For the synthesis of the title compound, see: Brahmachari & Banerjee (2014[Brahmachari, G. & Banerjee, B. (2014). ACS Sustainable Chem. Eng. 2, 411-422.]). For a related structure, see: Topno et al. (2011[Topno, N. S., Kumaravel, K., Kannan, M., Vasuki, G. & Krishna, R. (2011). Acta Cryst. E67, o956.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum.]).

[Scheme 1]

Experimental

Crystal data

  • C16H14N4O3·C2H6OS

  • Mr = 388.44

  • Monoclinic, P 21 /c

  • a = 28.018 (5) Å

  • b = 9.196 (5) Å

  • c = 15.396 (5) Å

  • β = 93.376 (5)°

  • V = 3960 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.805, Tmax = 1.000

  • 13653 measured reflections

  • 6946 independent reflections

  • 3460 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.210

  • S = 1.00

  • 6946 reflections

  • 510 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1B–C9B/C8B ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H2A⋯O1S 0.86 1.90 2.737 (4) 165
N2B—H2B⋯O2Si 0.86 1.90 2.750 (5) 168
N12A—H50A⋯N11Bii 0.86 2.19 3.024 (5) 164
N12A—H40A⋯O13Aiii 0.86 2.11 2.958 (4) 170
N12B—H50B⋯N11Aiv 0.86 2.23 3.072 (5) 165
N12B—H40B⋯O13Bv 0.86 2.10 2.945 (4) 168
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y+1, z+1; (iii) x, y+1, z; (iv) x, y-1, z-1; (v) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and 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.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1006444

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536814013270/lh5712sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013270/lh5712Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013270/lh5712Isup3.cml

checkCIF report


Comment top

Pyrano[2,3-c]pyrazole scaffolds represent a "privileged" structural motif well distributed in naturally occurring compounds with a broad spectrum of significant biological activities. Recently, a series of synthetic pyrano[2,3-c] pyrazole compounds have been evaluated and possess potent bactericidal (Nasr et al., 2002), insecticidal (Ismail et al., 2003), molluscicidal (Zonouz et al., 2012), analgestic (Kuo et al., 1984), anti-inflammatory activities (Zaki et al., 2006), hypotensive (Ahluwalia et al., 1997), hypoglycemic, and anticancer agents (Mohamed et al., 2010; Bhavanarushi et al., 2013). They are also potential inhibitors of human Chk1 kinase (Foloppe et al., 2006). Hence, investigation of the structural features of biologically relevant pyrano[2,3-c]pyrazole derivatives is of both scientific and practical interest. In continuation of our efforts to develop useful synthetic protocols for biologically significant molecules, we report herein an efficient and environmentally benign synthesis and the crystal structure of the title compound (I)

The asymmetric unit of the title compound is shown in Fig. 1. There are two crystallographically independent molecules (A and B). The geometry of both molecules is similar and in terms of their bond lengths and bond angles and are in good agreement with the standard values (Allen et al., 1987) and corresponds to those observed in a related structure (Topno et al., 2011). The double bond length C13A═O13A [1.212 (5) Å] and C13B═O13B [1.210 (5) Å] indicates the C═O double bond slightly longer than that observed for carbonyl bonds, probably because atoms O13A and O13B are involved in intermolecular N—H···O hydrogen bonds. The pyran ring (ring II) adopts a flattned sofa conformation in molecule A and a flattened boat conformation in molecule B with asymmetry parameters [ΔCs(C4) = 2.73] (molecule A) and [ΔCs(C4)) = 1.03, ΔC2(C4—C5) = 1.14] (molecule B) (Duax & Norton, 1975). The mean planes the pyrazole (ring I) and phenyl (ring III) rings from dihedral angles of 84.4 (2)° and 84.9 (2)°, respectively for molecules A and B. In the crystal, N—H···O and N—H···N hydrogen bonds link the components of the structure into chains along [010] (Fig. 2). In both solvent molecules, the S atoms are disordered over two sites with occupancy ratios of 0.679 (4):0.321 (4) and 0.546 (6):0.454 (6).

Related literature top

For background to the biological activity of synthetic pyrano[2,3-c] pyrazole compounds, see: Nasr et al. (2002); Ismail et al. (2003); Foloppe et al. (2006); Mohamed et al. (2010); Zonouz et al. (2012); Kuo et al. (1984); Zaki et al. (2006); Ahluwalia et al. (1997); Bhavanarushi et al. (2013). For the synthesis of the title compound, see: Brahmachari & Banerjee (2014). For a related structure, see: Topno et al. (2011). For standard bond-length data, see: Allen et al. (1987). For ring conformations, see: Duax & Norton (1975).

Experimental top

The synthesis of the title compound, ethyl 6-amino-5-cyano-4-phenyl-2, 4-dihydropyrano[2,3-c]pyrazole-3-carboxylate (I), was carried out via one-pot multi-component reaction in aqueous ethanol using low-cost and environmentally benign urea as catalyst at room temperature. An oven-dried screw cap test tube was charged with a magnetic stir bar, diethyl acetylenedicarboxylate (0.170 g, 1.0 mmol) and hydrazine hydrate (0.050 g, 1 mmol); the reaction mixture was then stirred at room temperature for about 10 min. After that, benzaldehyde (0.106 g, 1 mmol), malononitrile (0.066 g, 1.1 mmol), urea (0.007 g, 10 mol % as organo-catalyst) and EtOH:H2O (1:1 v/v; 4 ml) was added in a sequential manner (Brahmachari and Banerjee, 2014). The reaction mixture was then stirred vigorously at room temperature and the stirring was continued for 10 h. The progress of the reaction was monitored by TLC. On completion of the reaction, a solid mass was precipitated out, filtered off and repeatedly washed with aqueous ethanol to obtain a crude product which was purified just by recrystallization from ethanol without carrying out column chromatography. The structure of (I) was confirmed by analytical as well as spectral studies including 1H NMR, 13C NMR, and TOF-MS. The single crystal was obtained from DMSO as a solvent. For crystallization 50 mg of (I) dissolved in 5 ml DMSO was left for several days at ambient temperature which yielded white block shaped crystals. Ethyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c] pyrazole-3-carboxylate (1). White solid. Yield 91%. Mp: 521–523 K. 1H NMR (400 MHz, DMSO-d6) δ /p.p.m.: 13.76 (1H, s, NH), 7.28 (2H, t, J = 7.2 Hz, aromatic H), 7.19 (1H, t, J = 7.2 Hz, aromatic H), 7.10 (2H, d, J = 7.2 Hz, aromatic H), 7.03 (2H, s, NH2), 4.76 (1H, s, CH), 4.07 (2H, q, J = 7.2 \ 6.8 Hz, CH3), 1.03 (3H, t, J = 7.2 & 6.8 Hz, CH3). 13C NMR (100 MHz, DMSO-d6) δ /p.p.m.: 160.43, 158.56, 156.01, 145.31, 129.48, 128.66 (2 C), 127.73 (2 C), 127.04, 120.71, 104.03, 61.24, 58.32, 37.38, 14.14. TOF-MS: 333.0961 [M+Na]+. Elemental analysis: Calcd. (%) for C16H14N4O3: C, 61.93; H, 4.55; N, 18.06; found: C, C, 61.96; H, 4.53; N, 18.04.

Refinement top

All H atoms were geometrically fixed and allowed to ride on their parent C atoms, with C—H distances of 0.93–0.98 Å, N—H = 0.86Å and with Uiso(H) = 1.2Ueq(C,N).

Structure description top

Pyrano[2,3-c]pyrazole scaffolds represent a "privileged" structural motif well distributed in naturally occurring compounds with a broad spectrum of significant biological activities. Recently, a series of synthetic pyrano[2,3-c] pyrazole compounds have been evaluated and possess potent bactericidal (Nasr et al., 2002), insecticidal (Ismail et al., 2003), molluscicidal (Zonouz et al., 2012), analgestic (Kuo et al., 1984), anti-inflammatory activities (Zaki et al., 2006), hypotensive (Ahluwalia et al., 1997), hypoglycemic, and anticancer agents (Mohamed et al., 2010; Bhavanarushi et al., 2013). They are also potential inhibitors of human Chk1 kinase (Foloppe et al., 2006). Hence, investigation of the structural features of biologically relevant pyrano[2,3-c]pyrazole derivatives is of both scientific and practical interest. In continuation of our efforts to develop useful synthetic protocols for biologically significant molecules, we report herein an efficient and environmentally benign synthesis and the crystal structure of the title compound (I)

The asymmetric unit of the title compound is shown in Fig. 1. There are two crystallographically independent molecules (A and B). The geometry of both molecules is similar and in terms of their bond lengths and bond angles and are in good agreement with the standard values (Allen et al., 1987) and corresponds to those observed in a related structure (Topno et al., 2011). The double bond length C13A═O13A [1.212 (5) Å] and C13B═O13B [1.210 (5) Å] indicates the C═O double bond slightly longer than that observed for carbonyl bonds, probably because atoms O13A and O13B are involved in intermolecular N—H···O hydrogen bonds. The pyran ring (ring II) adopts a flattned sofa conformation in molecule A and a flattened boat conformation in molecule B with asymmetry parameters [ΔCs(C4) = 2.73] (molecule A) and [ΔCs(C4)) = 1.03, ΔC2(C4—C5) = 1.14] (molecule B) (Duax & Norton, 1975). The mean planes the pyrazole (ring I) and phenyl (ring III) rings from dihedral angles of 84.4 (2)° and 84.9 (2)°, respectively for molecules A and B. In the crystal, N—H···O and N—H···N hydrogen bonds link the components of the structure into chains along [010] (Fig. 2). In both solvent molecules, the S atoms are disordered over two sites with occupancy ratios of 0.679 (4):0.321 (4) and 0.546 (6):0.454 (6).

For background to the biological activity of synthetic pyrano[2,3-c] pyrazole compounds, see: Nasr et al. (2002); Ismail et al. (2003); Foloppe et al. (2006); Mohamed et al. (2010); Zonouz et al. (2012); Kuo et al. (1984); Zaki et al. (2006); Ahluwalia et al. (1997); Bhavanarushi et al. (2013). For the synthesis of the title compound, see: Brahmachari & Banerjee (2014). For a related structure, see: Topno et al. (2011). For standard bond-length data, see: Allen et al. (1987). For ring conformations, see: Duax & Norton (1975).

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); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I). with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure with hydrogen bonds shown as dahed lines.
Ethyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate dimethyl sulfoxide monosolvate top
Crystal data top
C16H14N4O3·C2H6OSF(000) = 1632
Mr = 388.44Dx = 1.303 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1789 reflections
a = 28.018 (5) Åθ = 4.1–26.7°
b = 9.196 (5) ŵ = 0.19 mm−1
c = 15.396 (5) ÅT = 293 K
β = 93.376 (5)°Block, white
V = 3960 (3) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		6946 independent reflections
Radiation source: fine-focus sealed tube3460 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 16.1049 pixels mm-1θmax = 25.0°, θmin = 3.4°
ω scansh = −31→33
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		k = −6→10
Tmin = 0.805, Tmax = 1.000l = −18→9
13653 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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0876P)2]
where P = (Fo2 + 2Fc2)/3
6946 reflections(Δ/σ)max < 0.001
510 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C16H14N4O3·C2H6OSV = 3960 (3) Å3
Mr = 388.44Z = 8
Monoclinic, P21/cMo Kα radiation
a = 28.018 (5) ŵ = 0.19 mm−1
b = 9.196 (5) ÅT = 293 K
c = 15.396 (5) Å0.30 × 0.20 × 0.20 mm
β = 93.376 (5)°
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		6946 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		3460 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 1.000Rint = 0.052
13653 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.210H-atom parameters constrained
S = 1.00Δρmax = 0.32 e Å−3
6946 reflectionsΔρmin = −0.24 e Å−3
510 parameters
Special details top

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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) top
xyzUiso*/UeqOcc. (<1)
N1A0.53193 (10)0.7819 (3)0.8897 (2)0.0695 (9)
N2A0.52515 (10)0.6372 (3)0.8921 (2)0.0677 (9)
H2A0.49740.59740.89170.081*
C3A0.56660 (11)0.5602 (3)0.8952 (2)0.0561 (9)
C4A0.65667 (11)0.6520 (3)0.8983 (2)0.0512 (8)
H4A0.66770.59070.94760.061*
C5A0.67549 (11)0.8066 (3)0.9139 (2)0.0502 (8)
C6A0.64854 (12)0.9290 (3)0.9073 (2)0.0571 (9)
O7A0.60010 (8)0.9282 (2)0.89259 (17)0.0674 (7)
C8A0.57909 (12)0.7925 (3)0.8921 (3)0.0616 (9)
C9A0.60339 (11)0.6616 (3)0.8957 (2)0.0530 (9)
C10A0.72495 (13)0.8238 (3)0.9324 (2)0.0585 (9)
N11A0.76529 (12)0.8350 (3)0.9473 (2)0.0823 (11)
N12A0.66396 (11)1.0672 (3)0.9145 (2)0.0810 (11)
H50A0.69391.08500.92430.097*
H40A0.64391.13770.90920.097*
C13A0.56757 (12)0.4028 (4)0.9000 (3)0.0638 (10)
O13A0.60412 (9)0.3324 (2)0.90798 (19)0.0771 (8)
O14A0.52397 (8)0.3481 (2)0.89287 (19)0.0786 (8)
C15A0.51823 (14)0.1906 (4)0.8995 (3)0.0886 (14)
H15C0.52530.15860.95890.106*
H15D0.53960.14100.86190.106*
C16A0.46789 (17)0.1595 (5)0.8721 (4)0.1174 (18)
H16D0.44730.21760.90560.176*
H16E0.46130.05830.88130.176*
H16F0.46230.18220.81150.176*
C17A0.67533 (11)0.5887 (3)0.8153 (2)0.0547 (9)
C18A0.66234 (14)0.6484 (4)0.7353 (3)0.0740 (11)
H18A0.64140.72700.73160.089*
C19A0.6800 (2)0.5929 (6)0.6608 (3)0.1099 (18)
H19A0.67100.63380.60710.132*
C20A0.7113 (2)0.4757 (8)0.6657 (5)0.128 (3)
H20A0.72380.43840.61560.154*
C21A0.72347 (18)0.4168 (6)0.7438 (5)0.118 (2)
H21A0.74420.33780.74710.141*
C22A0.70605 (13)0.4704 (4)0.8190 (3)0.0791 (12)
H22A0.71480.42730.87220.095*
N1B0.98769 (10)0.2450 (3)0.1030 (2)0.0690 (9)
N2B0.99344 (10)0.3898 (3)0.1081 (2)0.0637 (8)
H2B1.02030.43070.12310.076*
C3B0.95301 (11)0.4650 (3)0.0872 (2)0.0517 (8)
C4B0.86559 (10)0.3732 (3)0.0388 (2)0.0462 (8)
H4B0.86220.4317−0.01440.055*
C5B0.84917 (11)0.2186 (3)0.0175 (2)0.0490 (8)
C6B0.87600 (12)0.0964 (3)0.0311 (2)0.0575 (9)
O7B0.92214 (8)0.0970 (2)0.06421 (18)0.0714 (8)
C8B0.94166 (12)0.2333 (3)0.0776 (2)0.0595 (9)
C9B0.91763 (11)0.3640 (3)0.0674 (2)0.0478 (8)
C10B0.80137 (13)0.2011 (3)−0.0144 (2)0.0554 (9)
N11B0.76248 (11)0.1905 (3)−0.0413 (2)0.0784 (10)
N12B0.86195 (11)−0.0413 (3)0.0170 (2)0.0860 (11)
H50B0.8332−0.0594−0.00270.103*
H40B0.8817−0.11160.02760.103*
C13B0.95170 (12)0.6237 (3)0.0869 (2)0.0547 (9)
O13B0.91680 (8)0.6936 (2)0.06285 (18)0.0737 (8)
O14B0.99271 (8)0.6791 (2)0.11744 (18)0.0717 (8)
C15B0.99710 (13)0.8366 (3)0.1205 (3)0.0745 (11)
H15A0.97260.87840.15470.089*
H15B0.99400.87730.06230.089*
C16B1.04599 (15)0.8670 (4)0.1622 (3)0.0955 (14)
H16A1.04800.82950.22050.143*
H16B1.05150.97000.16360.143*
H16C1.06970.82080.12920.143*
C17B0.83482 (11)0.4393 (3)0.1059 (2)0.0532 (9)
C18B0.80440 (13)0.5537 (4)0.0831 (3)0.0793 (12)
H18B0.80490.59130.02700.095*
C19B0.77395 (18)0.6138 (6)0.1384 (5)0.1173 (19)
H19B0.75430.69120.12100.141*
C20B0.7730 (2)0.5589 (8)0.2185 (5)0.119 (2)
H20B0.75180.59850.25630.143*
C21B0.8023 (2)0.4450 (7)0.2477 (3)0.1114 (19)
H21B0.80130.40930.30410.134*
C22B0.83403 (15)0.3849 (4)0.1877 (3)0.0790 (12)
H22B0.85420.30850.20490.095*
S10.39614 (7)0.6010 (2)0.82388 (15)0.0969 (9)0.679 (4)
S1A0.39306 (13)0.6880 (5)0.8912 (3)0.0895 (19)0.321 (4)
S20.87312 (9)0.6108 (4)0.8352 (3)0.1088 (15)0.546 (6)
S2B0.88926 (12)0.5896 (3)0.7732 (3)0.0929 (15)0.454 (6)
O1S0.43139 (10)0.5574 (4)0.9002 (3)0.1292 (14)
O2S0.91562 (11)0.5181 (3)0.8424 (3)0.1368 (16)
C1S0.40250 (19)0.7830 (6)0.8178 (5)0.160 (3)
H1S0.43190.80550.79170.192*0.679 (4)
H2S0.40300.82390.87520.192*0.679 (4)
H3S0.37620.82320.78300.192*0.679 (4)
H4S0.43150.83650.83070.192*0.321 (4)
H5S0.37640.84960.80770.192*0.321 (4)
H6S0.40580.72490.76670.192*0.321 (4)
C2S0.34120 (18)0.5886 (6)0.8717 (5)0.158 (3)
H7S0.33310.48820.87910.190*0.679 (4)
H8S0.31690.63500.83480.190*0.679 (4)
H9S0.34340.63600.92730.190*0.679 (4)
H10S0.33620.52750.92090.190*0.321 (4)
H11S0.34400.52950.82090.190*0.321 (4)
H12S0.31460.65370.86250.190*0.321 (4)
C3S0.8903 (2)0.7740 (5)0.7998 (5)0.186 (3)
H13S0.91460.81310.83980.223*0.546 (6)
H14S0.86330.83850.79600.223*0.546 (6)
H15S0.90280.76380.74340.223*0.546 (6)
H16S0.92280.80590.80860.223*0.454 (6)
H17S0.87400.78900.85220.223*0.454 (6)
H18S0.87460.82860.75320.223*0.454 (6)
C4S0.8336 (3)0.5660 (7)0.7631 (8)0.290 (7)
H19S0.82110.47200.77650.348*0.546 (6)
H20S0.84740.56240.70750.348*0.546 (6)
H21S0.80820.63620.76120.348*0.546 (6)
H22S0.82690.46620.74850.348*0.454 (6)
H23S0.82020.62780.71770.348*0.454 (6)
H24S0.81980.58940.81690.348*0.454 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0434 (18)0.0496 (17)0.116 (3)0.0062 (13)0.0079 (18)0.0038 (17)
N2A0.0419 (17)0.0522 (18)0.110 (3)0.0025 (13)0.0132 (17)0.0062 (17)
C3A0.0414 (19)0.0483 (19)0.079 (2)0.0043 (16)0.0087 (18)0.0002 (17)
C4A0.0442 (19)0.0511 (18)0.058 (2)0.0037 (15)0.0051 (16)0.0021 (16)
C5A0.0453 (19)0.0419 (17)0.063 (2)0.0083 (15)−0.0021 (16)−0.0056 (15)
C6A0.0456 (19)0.049 (2)0.076 (2)−0.0005 (16)−0.0011 (18)−0.0025 (17)
O7A0.0427 (13)0.0423 (13)0.116 (2)0.0063 (10)−0.0014 (14)0.0028 (13)
C8A0.046 (2)0.048 (2)0.091 (3)0.0053 (16)0.0059 (19)0.0017 (19)
C9A0.0428 (19)0.0455 (18)0.071 (2)0.0135 (16)0.0085 (17)0.0045 (16)
C10A0.052 (2)0.0449 (19)0.078 (3)0.0035 (16)−0.007 (2)−0.0057 (17)
N11A0.054 (2)0.065 (2)0.126 (3)0.0044 (16)−0.017 (2)−0.0027 (19)
N12A0.0544 (19)0.0475 (17)0.139 (3)0.0040 (15)−0.013 (2)−0.0031 (18)
C13A0.039 (2)0.055 (2)0.098 (3)0.0024 (17)0.013 (2)0.001 (2)
O13A0.0498 (15)0.0545 (14)0.128 (2)0.0064 (12)0.0092 (15)−0.0029 (14)
O14A0.0476 (15)0.0529 (14)0.135 (2)−0.0020 (12)0.0061 (16)0.0037 (15)
C15A0.068 (3)0.050 (2)0.148 (4)−0.0094 (19)0.008 (3)0.007 (2)
C16A0.081 (3)0.088 (3)0.182 (5)−0.024 (3)−0.006 (4)−0.005 (3)
C17A0.0368 (18)0.0492 (19)0.079 (3)−0.0042 (15)0.0072 (18)−0.0056 (18)
C18A0.074 (3)0.070 (2)0.079 (3)−0.013 (2)0.011 (2)−0.006 (2)
C19A0.127 (5)0.124 (4)0.082 (3)−0.051 (4)0.040 (3)−0.025 (3)
C20A0.095 (5)0.142 (6)0.153 (6)−0.046 (4)0.064 (5)−0.085 (5)
C21A0.065 (3)0.119 (4)0.173 (6)0.009 (3)0.036 (4)−0.066 (5)
C22A0.048 (2)0.073 (3)0.116 (4)0.0119 (19)0.010 (2)−0.017 (2)
N1B0.0415 (17)0.0492 (16)0.115 (3)−0.0001 (13)−0.0089 (17)0.0045 (17)
N2B0.0425 (17)0.0493 (17)0.098 (2)−0.0002 (13)−0.0072 (16)0.0051 (16)
C3B0.0394 (18)0.0441 (18)0.071 (2)0.0053 (15)0.0009 (17)0.0052 (16)
C4B0.0385 (17)0.0445 (17)0.0552 (19)0.0047 (14)0.0004 (15)0.0006 (15)
C5B0.0398 (18)0.0418 (17)0.064 (2)0.0058 (14)−0.0055 (16)−0.0009 (15)
C6B0.0425 (19)0.0478 (19)0.081 (3)0.0004 (16)−0.0052 (18)0.0016 (18)
O7B0.0514 (15)0.0407 (13)0.120 (2)0.0091 (11)−0.0164 (15)0.0007 (13)
C8B0.049 (2)0.0416 (19)0.087 (3)0.0041 (16)−0.0036 (19)−0.0002 (18)
C9B0.0418 (18)0.0410 (17)0.060 (2)0.0055 (14)−0.0018 (16)0.0017 (15)
C10B0.050 (2)0.0428 (18)0.072 (2)−0.0001 (15)−0.0093 (19)−0.0079 (16)
N11B0.056 (2)0.0639 (19)0.111 (3)0.0036 (16)−0.023 (2)−0.0106 (18)
N12B0.0582 (19)0.0449 (16)0.151 (3)0.0027 (14)−0.027 (2)−0.0107 (19)
C13B0.0408 (19)0.052 (2)0.071 (2)0.0008 (16)−0.0001 (18)0.0024 (18)
O13B0.0480 (15)0.0526 (14)0.119 (2)0.0049 (11)−0.0078 (15)0.0049 (14)
O14B0.0503 (15)0.0462 (13)0.117 (2)−0.0033 (11)−0.0111 (15)0.0011 (13)
C15B0.064 (3)0.047 (2)0.112 (3)−0.0085 (18)0.006 (2)−0.006 (2)
C16B0.083 (3)0.076 (3)0.126 (4)−0.027 (2)−0.005 (3)−0.009 (3)
C17B0.0435 (19)0.0493 (19)0.067 (2)−0.0116 (16)0.0032 (17)−0.0086 (16)
C18B0.054 (2)0.076 (3)0.109 (3)0.017 (2)0.010 (2)−0.018 (2)
C19B0.075 (4)0.134 (5)0.146 (5)0.020 (3)0.029 (4)−0.053 (4)
C20B0.082 (4)0.135 (5)0.145 (6)−0.024 (4)0.047 (4)−0.062 (5)
C21B0.126 (5)0.136 (5)0.075 (3)−0.068 (4)0.035 (3)−0.029 (3)
C22B0.087 (3)0.077 (3)0.074 (3)−0.016 (2)0.013 (2)−0.007 (2)
S10.0793 (13)0.0955 (14)0.1160 (19)−0.0053 (10)0.0069 (12)−0.0162 (12)
S1A0.065 (2)0.121 (4)0.083 (3)0.018 (2)0.0102 (19)0.013 (2)
S20.0635 (16)0.153 (3)0.111 (3)0.0201 (15)0.0120 (16)0.056 (2)
S2B0.0635 (19)0.114 (2)0.101 (3)−0.0011 (15)0.0044 (19)−0.0174 (17)
O1S0.0506 (17)0.134 (3)0.203 (4)0.0091 (17)0.006 (2)0.077 (3)
O2S0.067 (2)0.092 (2)0.245 (5)0.0036 (17)−0.047 (3)0.029 (2)
C1S0.086 (4)0.125 (4)0.270 (8)0.003 (3)0.004 (5)0.099 (5)
C2S0.067 (3)0.160 (5)0.245 (8)−0.025 (3)−0.012 (4)0.086 (5)
C3S0.127 (5)0.088 (4)0.333 (10)−0.006 (3)−0.069 (6)0.031 (5)
C4S0.142 (6)0.142 (6)0.56 (2)0.003 (5)−0.198 (10)−0.020 (8)
Geometric parameters (Å, º) top
N1A—C8A1.323 (4)C13B—O14B1.318 (4)
N1A—N2A1.345 (4)O14B—C15B1.454 (4)
N2A—C3A1.359 (4)C15B—C16B1.505 (5)
N2A—H2A0.8600C15B—H15A0.9700
C3A—C9A1.390 (4)C15B—H15B0.9700
C3A—C13A1.450 (5)C16B—H16A0.9600
C4A—C9A1.494 (4)C16B—H16B0.9600
C4A—C17A1.524 (4)C16B—H16C0.9600
C4A—C5A1.530 (4)C17B—C22B1.357 (5)
C4A—H4A0.9800C17B—C18B1.387 (5)
C5A—C6A1.356 (4)C18B—C19B1.358 (6)
C5A—C10A1.407 (4)C18B—H18B0.9300
C6A—N12A1.345 (4)C19B—C20B1.333 (8)
C6A—O7A1.363 (4)C19B—H19B0.9300
O7A—C8A1.379 (4)C20B—C21B1.390 (7)
C8A—C9A1.383 (4)C20B—H20B0.9300
C10A—N11A1.145 (4)C21B—C22B1.430 (6)
N12A—H50A0.8600C21B—H21B0.9300
N12A—H40A0.8600C22B—H22B0.9300
C13A—O13A1.212 (4)S1—O1S1.543 (4)
C13A—O14A1.319 (4)S1—C1S1.686 (5)
O14A—C15A1.462 (4)S1—C2S1.749 (6)
C15A—C16A1.476 (5)S1—H6S1.4746
C15A—H15C0.9700S1—H11S1.6005
C15A—H15D0.9700S1A—C1S1.464 (6)
C16A—H16D0.9600S1A—O1S1.612 (5)
C16A—H16E0.9600S1A—C2S1.728 (6)
C16A—H16F0.9600S2—O2S1.463 (4)
C17A—C18A1.378 (5)S2—C4S1.576 (8)
C17A—C22A1.387 (5)S2—C3S1.677 (6)
C18A—C19A1.374 (6)S2—H17S1.6594
C18A—H18A0.9300S2—H24S1.5180
C19A—C20A1.390 (8)S2B—O2S1.421 (5)
C19A—H19A0.9300S2B—C4S1.573 (8)
C20A—C21A1.344 (8)S2B—C3S1.744 (6)
C20A—H20A0.9300C1S—H1S0.9600
C21A—C22A1.374 (7)C1S—H2S0.9600
C21A—H21A0.9300C1S—H3S0.9600
C22A—H22A0.9300C1S—H4S0.9600
N1B—C8B1.330 (4)C1S—H5S0.9600
N1B—N2B1.344 (4)C1S—H6S0.9601
N2B—C3B1.350 (4)C2S—H7S0.9600
N2B—H2B0.8600C2S—H8S0.9600
C3B—C9B1.379 (4)C2S—H9S0.9600
C3B—C13B1.459 (4)C2S—H10S0.9600
C4B—C9B1.501 (4)C2S—H11S0.9600
C4B—C17B1.511 (4)C2S—H12S0.9600
C4B—C5B1.524 (4)C3S—H13S0.9600
C4B—H4B0.9800C3S—H14S0.9600
C5B—C6B1.361 (4)C3S—H15S0.9600
C5B—C10B1.408 (4)C3S—H16S0.9600
C6B—N12B1.340 (4)C3S—H17S0.9600
C6B—O7B1.362 (4)C3S—H18S0.9600
O7B—C8B1.378 (4)C4S—H19S0.9600
C8B—C9B1.382 (4)C4S—H20S0.9600
C10B—N11B1.147 (4)C4S—H21S0.9600
N12B—H50B0.8600C4S—H22S0.9600
N12B—H40B0.8600C4S—H23S0.9600
C13B—O13B1.210 (4)C4S—H24S0.9600
C8A—N1A—N2A102.4 (3)O1S—S1—C1S103.6 (3)
N1A—N2A—C3A113.3 (3)O1S—S1—C2S101.7 (3)
N1A—N2A—H2A123.4C1S—S1—C2S100.8 (3)
C3A—N2A—H2A123.4O1S—S1—H6S121.5
N2A—C3A—C9A106.4 (3)C2S—S1—H6S120.0
N2A—C3A—C13A122.4 (3)O1S—S1—H11S117.2
C9A—C3A—C13A131.2 (3)C1S—S1—H11S120.4
C9A—C4A—C17A113.1 (3)H6S—S1—H11S120.0
C9A—C4A—C5A106.5 (2)C1S—S1A—O1S111.2 (4)
C17A—C4A—C5A110.7 (3)C1S—S1A—C2S111.7 (4)
C9A—C4A—H4A108.8O1S—S1A—C2S99.8 (3)
C17A—C4A—H4A108.8O2S—S2—C4S115.8 (5)
C5A—C4A—H4A108.8O2S—S2—C3S107.4 (3)
C6A—C5A—C10A117.3 (3)C4S—S2—C3S102.0 (4)
C6A—C5A—C4A125.1 (3)O2S—S2—H17S124.0
C10A—C5A—C4A117.6 (3)C4S—S2—H17S111.9
N12A—C6A—C5A127.1 (3)O2S—S2—H24S136.6
N12A—C6A—O7A109.3 (3)C3S—S2—H24S110.7
C5A—C6A—O7A123.6 (3)H17S—S2—H24S99.3
C6A—O7A—C8A115.2 (2)O2S—S2B—C4S118.6 (5)
N1A—C8A—O7A119.5 (3)O2S—S2B—C3S105.9 (3)
N1A—C8A—C9A115.2 (3)C4S—S2B—C3S99.2 (4)
O7A—C8A—C9A125.3 (3)S1—O1S—S1A49.26 (17)
C8A—C9A—C3A102.8 (3)S1A—C1S—S148.8 (2)
C8A—C9A—C4A122.8 (3)S1A—C1S—H1S130.5
C3A—C9A—C4A134.4 (3)S1—C1S—H1S109.5
N11A—C10A—C5A178.7 (4)S1A—C1S—H2S61.1
C6A—N12A—H50A120.0S1—C1S—H2S109.5
C6A—N12A—H40A120.0H1S—C1S—H2S109.5
H50A—N12A—H40A120.0S1A—C1S—H3S119.5
O13A—C13A—O14A125.3 (3)S1—C1S—H3S109.5
O13A—C13A—C3A123.5 (3)H1S—C1S—H3S109.5
O14A—C13A—C3A111.2 (3)H2S—C1S—H3S109.5
C13A—O14A—C15A118.5 (3)S1A—C1S—H4S109.6
O14A—C15A—C16A106.2 (3)S1—C1S—H4S126.0
O14A—C15A—H15C110.5H2S—C1S—H4S69.0
C16A—C15A—H15C110.5H3S—C1S—H4S122.0
O14A—C15A—H15D110.5S1A—C1S—H5S109.5
C16A—C15A—H15D110.5S1—C1S—H5S124.1
H15C—C15A—H15D108.7H1S—C1S—H5S117.4
C15A—C16A—H16D109.5H2S—C1S—H5S82.5
C15A—C16A—H16E109.5H4S—C1S—H5S109.5
H16D—C16A—H16E109.5S1A—C1S—H6S109.3
C15A—C16A—H16F109.5S1—C1S—H6S60.6
H16D—C16A—H16F109.5H1S—C1S—H6S69.5
H16E—C16A—H16F109.5H2S—C1S—H6S167.3
C18A—C17A—C22A118.7 (4)H3S—C1S—H6S82.3
C18A—C17A—C4A120.8 (3)H4S—C1S—H6S109.5
C22A—C17A—C4A120.5 (3)H5S—C1S—H6S109.5
C19A—C18A—C17A120.6 (4)S1A—C2S—H7S133.7
C19A—C18A—H18A119.7S1—C2S—H7S109.5
C17A—C18A—H18A119.7S1A—C2S—H8S115.3
C18A—C19A—C20A120.0 (5)S1—C2S—H8S109.5
C18A—C19A—H19A120.0H7S—C2S—H8S109.5
C20A—C19A—H19A120.0S1A—C2S—H9S66.1
C21A—C20A—C19A119.1 (5)S1—C2S—H9S109.5
C21A—C20A—H20A120.4H7S—C2S—H9S109.5
C19A—C20A—H20A120.4H8S—C2S—H9S109.5
C20A—C21A—C22A121.7 (5)S1A—C2S—H10S109.4
C20A—C21A—H21A119.1S1—C2S—H10S122.8
C22A—C21A—H21A119.1H7S—C2S—H10S45.2
C21A—C22A—C17A119.8 (5)H8S—C2S—H10S126.6
C21A—C22A—H22A120.1H9S—C2S—H10S64.3
C17A—C22A—H22A120.1S1A—C2S—H11S109.5
C8B—N1B—N2B102.0 (3)S1—C2S—H11S65.0
N1B—N2B—C3B113.4 (3)H7S—C2S—H11S65.4
N1B—N2B—H2B123.3H8S—C2S—H11S81.9
C3B—N2B—H2B123.3H9S—C2S—H11S168.7
N2B—C3B—C9B106.8 (3)H10S—C2S—H11S109.5
N2B—C3B—C13B122.2 (3)S1A—C2S—H12S109.5
C9B—C3B—C13B130.9 (3)S1—C2S—H12S126.4
C9B—C4B—C17B113.9 (3)H7S—C2S—H12S115.5
C9B—C4B—C5B106.6 (2)H9S—C2S—H12S81.8
C17B—C4B—C5B110.2 (2)H10S—C2S—H12S109.5
C9B—C4B—H4B108.7H11S—C2S—H12S109.5
C17B—C4B—H4B108.7S2—C3S—H13S109.5
C5B—C4B—H4B108.7S2B—C3S—H13S121.1
C6B—C5B—C10B117.7 (3)S2—C3S—H14S109.5
C6B—C5B—C4B125.5 (3)S2B—C3S—H14S125.8
C10B—C5B—C4B116.8 (2)H13S—C3S—H14S109.5
N12B—C6B—C5B126.9 (3)S2—C3S—H15S109.5
N12B—C6B—O7B109.1 (3)S2B—C3S—H15S72.2
C5B—C6B—O7B123.9 (3)H13S—C3S—H15S109.5
C6B—O7B—C8B114.8 (2)H14S—C3S—H15S109.5
N1B—C8B—O7B119.1 (3)S2—C3S—H16S121.1
N1B—C8B—C9B114.9 (3)S2B—C3S—H16S109.4
O7B—C8B—C9B126.0 (3)H14S—C3S—H16S123.9
C3B—C9B—C8B102.8 (3)H15S—C3S—H16S76.3
C3B—C9B—C4B134.4 (3)S2—C3S—H17S72.3
C8B—C9B—C4B122.7 (3)S2B—C3S—H17S109.6
N11B—C10B—C5B178.2 (4)H13S—C3S—H17S76.3
C6B—N12B—H50B120.0H14S—C3S—H17S63.3
C6B—N12B—H40B120.0H15S—C3S—H17S172.4
H50B—N12B—H40B120.0H16S—C3S—H17S109.5
O13B—C13B—O14B125.1 (3)S2—C3S—H18S125.7
O13B—C13B—C3B123.5 (3)S2B—C3S—H18S109.4
O14B—C13B—C3B111.4 (3)H13S—C3S—H18S123.9
C13B—O14B—C15B117.9 (3)H14S—C3S—H18S46.2
O14B—C15B—C16B105.8 (3)H15S—C3S—H18S63.3
O14B—C15B—H15A110.6H16S—C3S—H18S109.5
C16B—C15B—H15A110.6H17S—C3S—H18S109.5
O14B—C15B—H15B110.6S2B—C4S—H19S118.3
C16B—C15B—H15B110.6S2—C4S—H19S109.5
H15A—C15B—H15B108.7S2B—C4S—H20S69.1
C15B—C16B—H16A109.5S2—C4S—H20S109.5
C15B—C16B—H16B109.5H19S—C4S—H20S109.5
H16A—C16B—H16B109.5S2B—C4S—H21S129.7
C15B—C16B—H16C109.5S2—C4S—H21S109.5
H16A—C16B—H16C109.5H19S—C4S—H21S109.5
H16B—C16B—H16C109.5H20S—C4S—H21S109.5
C22B—C17B—C18B118.1 (4)S2B—C4S—H22S109.5
C22B—C17B—C4B121.8 (3)S2—C4S—H22S122.2
C18B—C17B—C4B119.9 (3)H20S—C4S—H22S80.9
C19B—C18B—C17B123.3 (5)H21S—C4S—H22S120.2
C19B—C18B—H18B118.3S2B—C4S—H23S109.6
C17B—C18B—H18B118.3S2—C4S—H23S125.9
C20B—C19B—C18B118.3 (6)H19S—C4S—H23S123.9
C20B—C19B—H19B120.9H20S—C4S—H23S62.2
C18B—C19B—H19B120.9H21S—C4S—H23S47.3
C19B—C20B—C21B122.7 (5)H22S—C4S—H23S109.5
C19B—C20B—H20B118.6S2B—C4S—H24S109.4
C21B—C20B—H20B118.6S2—C4S—H24S68.7
C20B—C21B—C22B117.4 (5)H19S—C4S—H24S81.1
C20B—C21B—H21B121.3H20S—C4S—H24S168.9
C22B—C21B—H21B121.3H21S—C4S—H24S62.5
C17B—C22B—C21B120.1 (5)H22S—C4S—H24S109.5
C17B—C22B—H22B119.9H23S—C4S—H24S109.5
C21B—C22B—H22B119.9
C8A—N1A—N2A—C3A−0.4 (4)C5B—C6B—O7B—C8B−4.7 (5)
N1A—N2A—C3A—C9A0.6 (4)N2B—N1B—C8B—O7B179.4 (3)
N1A—N2A—C3A—C13A178.7 (3)N2B—N1B—C8B—C9B−0.8 (4)
C9A—C4A—C5A—C6A−12.8 (4)C6B—O7B—C8B—N1B−174.5 (3)
C17A—C4A—C5A—C6A110.5 (4)C6B—O7B—C8B—C9B5.8 (5)
C9A—C4A—C5A—C10A170.4 (3)N2B—C3B—C9B—C8B−0.9 (4)
C17A—C4A—C5A—C10A−66.3 (4)C13B—C3B—C9B—C8B178.2 (3)
C10A—C5A—C6A—N12A1.7 (5)N2B—C3B—C9B—C4B−179.2 (3)
C4A—C5A—C6A—N12A−175.1 (3)C13B—C3B—C9B—C4B−0.1 (6)
C10A—C5A—C6A—O7A−177.7 (3)N1B—C8B—C9B—C3B1.1 (4)
C4A—C5A—C6A—O7A5.5 (5)O7B—C8B—C9B—C3B−179.1 (3)
N12A—C6A—O7A—C8A−174.1 (3)N1B—C8B—C9B—C4B179.7 (3)
C5A—C6A—O7A—C8A5.4 (5)O7B—C8B—C9B—C4B−0.6 (5)
N2A—N1A—C8A—O7A−178.6 (3)C17B—C4B—C9B—C3B−65.1 (5)
N2A—N1A—C8A—C9A0.1 (5)C5B—C4B—C9B—C3B173.1 (4)
C6A—O7A—C8A—N1A171.2 (3)C17B—C4B—C9B—C8B116.8 (3)
C6A—O7A—C8A—C9A−7.3 (5)C5B—C4B—C9B—C8B−5.0 (4)
N1A—C8A—C9A—C3A0.2 (5)N2B—C3B—C13B—O13B174.8 (3)
O7A—C8A—C9A—C3A178.8 (4)C9B—C3B—C13B—O13B−4.2 (6)
N1A—C8A—C9A—C4A179.7 (3)N2B—C3B—C13B—O14B−6.4 (4)
O7A—C8A—C9A—C4A−1.7 (6)C9B—C3B—C13B—O14B174.6 (4)
N2A—C3A—C9A—C8A−0.5 (4)O13B—C13B—O14B—C15B−1.8 (5)
C13A—C3A—C9A—C8A−178.3 (4)C3B—C13B—O14B—C15B179.5 (3)
N2A—C3A—C9A—C4A−179.8 (4)C13B—O14B—C15B—C16B177.0 (3)
C13A—C3A—C9A—C4A2.4 (7)C9B—C4B—C17B—C22B−55.6 (4)
C17A—C4A—C9A—C8A−111.1 (4)C5B—C4B—C17B—C22B64.2 (4)
C5A—C4A—C9A—C8A10.7 (4)C9B—C4B—C17B—C18B127.9 (3)
C17A—C4A—C9A—C3A68.1 (5)C5B—C4B—C17B—C18B−112.3 (3)
C5A—C4A—C9A—C3A−170.0 (4)C22B—C17B—C18B—C19B0.0 (6)
N2A—C3A—C13A—O13A−175.5 (4)C4B—C17B—C18B—C19B176.5 (4)
C9A—C3A—C13A—O13A2.1 (7)C17B—C18B—C19B—C20B−0.7 (7)
N2A—C3A—C13A—O14A5.7 (5)C18B—C19B—C20B—C21B1.1 (9)
C9A—C3A—C13A—O14A−176.7 (4)C19B—C20B—C21B—C22B−0.9 (8)
O13A—C13A—O14A—C15A3.4 (6)C18B—C17B—C22B—C21B0.3 (5)
C3A—C13A—O14A—C15A−177.8 (3)C4B—C17B—C22B—C21B−176.2 (3)
C13A—O14A—C15A—C16A−169.0 (4)C20B—C21B—C22B—C17B0.1 (6)
C9A—C4A—C17A—C18A54.5 (4)C1S—S1—O1S—S1A45.2 (3)
C5A—C4A—C17A—C18A−64.9 (4)C2S—S1—O1S—S1A−59.0 (3)
C9A—C4A—C17A—C22A−126.0 (3)C1S—S1A—O1S—S1−58.4 (4)
C5A—C4A—C17A—C22A114.6 (3)C2S—S1A—O1S—S159.6 (3)
C22A—C17A—C18A—C19A−0.8 (5)C4S—S2B—O2S—S2−51.6 (5)
C4A—C17A—C18A—C19A178.7 (3)C3S—S2B—O2S—S258.6 (3)
C17A—C18A—C19A—C20A−0.1 (7)C4S—S2—O2S—S2B49.6 (6)
C18A—C19A—C20A—C21A0.9 (8)C3S—S2—O2S—S2B−63.5 (4)
C19A—C20A—C21A—C22A−0.6 (9)O1S—S1A—C1S—S151.7 (3)
C20A—C21A—C22A—C17A−0.4 (8)C2S—S1A—C1S—S1−58.8 (4)
C18A—C17A—C22A—C21A1.1 (6)O1S—S1—C1S—S1A−51.9 (3)
C4A—C17A—C22A—C21A−178.4 (4)C2S—S1—C1S—S1A53.0 (3)
C8B—N1B—N2B—C3B0.2 (4)C1S—S1A—C2S—S162.2 (4)
N1B—N2B—C3B—C9B0.5 (4)O1S—S1A—C2S—S1−55.3 (3)
N1B—N2B—C3B—C13B−178.7 (3)O1S—S1—C2S—S1A59.9 (3)
C9B—C4B—C5B—C6B6.1 (4)C1S—S1—C2S—S1A−46.6 (3)
C17B—C4B—C5B—C6B−118.0 (4)O2S—S2—C3S—S2B57.7 (3)
C9B—C4B—C5B—C10B−177.6 (3)C4S—S2—C3S—S2B−64.5 (5)
C17B—C4B—C5B—C10B58.3 (4)O2S—S2B—C3S—S2−59.7 (3)
C10B—C5B—C6B—N12B0.3 (6)C4S—S2B—C3S—S263.7 (5)
C4B—C5B—C6B—N12B176.6 (3)O2S—S2B—C4S—S251.5 (4)
C10B—C5B—C6B—O7B−177.9 (3)C3S—S2B—C4S—S2−62.3 (4)
C4B—C5B—C6B—O7B−1.5 (5)O2S—S2—C4S—S2B−47.8 (5)
N12B—C6B—O7B—C8B176.9 (3)C3S—S2—C4S—S2B68.4 (4)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1B–C9B/C8B ring.
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1S0.861.902.737 (4)165
N2B—H2B···O2Si0.861.902.750 (5)168
N12A—H50A···N11Bii0.862.193.024 (5)164
N12A—H40A···O13Aiii0.862.112.958 (4)170
N12B—H50B···N11Aiv0.862.233.072 (5)165
N12B—H40B···O13Bv0.862.102.945 (4)168
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y+1, z+1; (iii) x, y+1, z; (iv) x, y−1, z−1; (v) x, y−1, z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1B–C9B/C8B ring.
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1S0.861.902.737 (4)165
N2B—H2B···O2Si0.861.902.750 (5)168
N12A—H50A···N11Bii0.862.193.024 (5)164
N12A—H40A···O13Aiii0.862.112.958 (4)170
N12B—H50B···N11Aiv0.862.233.072 (5)165
N12B—H40B···O13Bv0.862.102.945 (4)168
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y+1, z+1; (iii) x, y+1, z; (iv) x, y−1, z−1; (v) x, y−1, z.
 

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. GB is thankful to the CSIR, New Delhi, for financial support [grant No. 02 (110)/12/EMR-II]. BB is grateful to the UGC, New Delhi for the award of a Senior Research Fellowship.

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ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o795-o796
https://doi.org/10.1107/S1600536814013270
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