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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 3| March 2014| Pages o279-o280
doi:10.1107/S1600536814002712

(3aR*,8bR*)-3a,8b-Dihy­dr­oxy-1-(4-methyl­phen­yl)-2-methyl­sulfanyl-3-nitro-1,8b-di­hydro­indeno­[1,2-b]pyrrol-4(3aH)-one

R. A. Nagalakshmi,a J. Suresh,a R. Ranjith Kumar,b V. Jeyachandranb and P. L. Nilantha Lakshmanc*

aDepartment of Physics, The Madura College, Madurai 625 011, India, bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 26 January 2014; accepted 5 February 2014; online 12 February 2014)

The asymmetric unit of the title compound, C19H16N2O5S, contains four independent mol­ecules (A, B, C and D), with two mol­ecules (B and D) displaying disorder in their methyl­sulfanyl groups [occupancy ratios of 0.797 (11):0.203 (11) and 0.85 (2):0.15 (2)]. The nitro groups are twisted slightly out of the planes of the 2-pyrroline rings to which they are bonded with dihedral angles of 10.17 (1), 8.01 (1), 9.44 (1) and 8.87 (1)° in mol­ecules A, B, C and D, respectively. The 2-pyrroline rings are almost orthogonal to the attached tolyl rings, forming dihedral angles of 73.44 (1), 81.21 (1), 88.18 (8) and 73.94 (1)° for mol­ecules A, B, C and D, respectively. A weak intra­molecular O—H⋯O inter­action is observed in mol­ecules B and C. The two hy­droxy groups in each mol­ecule are involved in inter­molecular O—H⋯O hydrogen bonding. In the crystal, mol­ecules are connected via O—H⋯O and C—H⋯O hydrogen bonds, forming a complex three-dimensional network.

CCDC reference: 985344

Related literature

For the importance of pyrrolidine and pyrroline derivatives, see: Obniska et al. (2002[Obniska, J., Zeic, A. & Zagorska, A. (2002). Acta Pol. Pharm. 59, 209-213.]); Stylianakis et al. (2003[Stylianakis, I., Kolocouris, A., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & De Clercq, E. (2003). Bioorg. Med. Chem. Lett. 13, 1699-1703.]); Coldham & Hufton (2005[Coldham, I. & Hufton, R. (2005). Chem. Rev. 105, 2765-2810.]); Kravchenko et al. (2005[Kravchenko, D. V., Kysil, V. M., Tkachenko, S. E., Maliarchouk, S., Okun, I. M. & Ivachtchenko, A. V. (2005). Eur. J. Med. Chem. 40, 1377-1383.]); Nair & Suja (2007[Nair, V. & Suja, T. D. (2007). Tetrahedron, 63, 12247-12275.]); Pandey et al. (2006[Pandey, G., Banerjee, P. & Gadre, S. R. (2006). Chem. Rev. 106, 4484-4517.]). For a related structure, see: Nagalakshmi et al. (2013[Nagalakshmi, R. A., Suresh, J., Jeyachandran, V., Kumar, R. R. & Lakshman, P. L. N. (2013). Acta Cryst. E69, o1849-o1850.]). For ring conformation parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C19H16N2O5S

  • Mr = 384.40

  • Triclinic, [P \overline 1]

  • a = 10.0830 (5) Å

  • b = 10.2775 (5) Å

  • c = 34.6579 (17) Å

  • α = 97.540 (3)°

  • β = 96.028 (3)°

  • γ = 97.138 (3)°

  • V = 3505.9 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm
Data collection

  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 53951 measured reflections

  • 13050 independent reflections

  • 9856 reflections with I > 2σ(I)

  • Rint = 0.041
Refinement

  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 0.188

  • S = 1.06

  • 13050 reflections

  • 1016 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3B—H3B⋯O5B 0.82 2.19 2.748 (4) 125
O3C—H3C⋯O5C 0.82 2.17 2.728 (4) 126
O2A—H2A⋯O3Ai 0.82 1.97 2.785 (3) 175
O3A—H3A⋯O3Bii 0.82 2.04 2.854 (3) 172
O2B—H2B⋯O1Aiii 0.82 2.01 2.787 (3) 157
O2C—H2C⋯O5Div 0.82 2.57 3.133 (4) 127
O2C—H2C⋯O1Div 0.82 2.03 2.797 (4) 155
O3D—H3D⋯O3Civ 0.82 2.04 2.857 (3) 175
C10A—H10A⋯O5Aiii 0.93 2.54 3.347 (5) 146
C10C—H10C⋯O5Cv 0.93 2.50 3.331 (6) 149
C10D—H10D⋯O5Dv 0.93 2.59 3.437 (5) 151
C10B—H10B⋯O5Bii 0.93 2.53 3.316 (6) 142
C2—H20⋯O1Cvi 0.96 2.50 3.446 (7) 170
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y, z; (iv) -x+1, -y+2, -z+2; (v) x, y-1, z; (vi) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 985344

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814002712/bh2494sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002712/bh2494Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002712/bh2494Isup3.cml

checkCIF report


Comment top

Pyrrolidine-containing compounds form an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products (Coldham & Hufton, 2005; Kravchenko et al., 2005; Nair & Suja, 2007; Pandey et al., 2006). Pyrrolidine derivatives possess anti-influenza (Stylianakis et al., 2003) and anti-convulsant (Obniska et al., 2002) activities. The high medicinal values of these compounds, in conjunction with our research interests, prompted us to synthesize and report the X-ray study of the title compound. The same compound with the p-tolyl group replaced by a p-methoxyphenyl group was previously reported (Nagalakshmi et al., 2013).

The asymmetric unit of the title compound, C19H16N2O5S, contains four crystallographically independent molecules A, B, C and D (shown in Figs. 1, 2, 3 and 4, respectively), with two molecules (A and C) exhibiting similar geometries and the other two molecules (B and D) displaying disorder. The 2-pyrroline rings of molecules A and D are planar with r.m.s. deviations of 0.0277 (1) and 0.0234 (1) Å; molecules B and C adopt a slightly twisted conformation for these rings, with puckering parameters Q = 0.112 (4) Å, φ2 = 231 (2)° and Q = 0.080 (4) Å, φ2 = 226 (3)°, respectively (Cremer & Pople, 1975). The cyclopentane rings of molecules A and D are planar. Molecule B adopts a twisted cyclopentane conformation, with puckering parameters Q = 0.098 (4) Å, φ2 = 231 (2)°; molecule C adopts an envelope cyclopentane conformation with puckering parameters Q = 0.078 (4) Å and φ2 = 351 (3)°. The 2-pyrroline rings are almost orthogonal to the attached tolyl rings in all molecules, forming dihedral angles of 73.44 (1), 81.21 (1), 88.18 (8) and 73.94 (1)° for molecules A, B, C and D, respectively. The nitro group (N2/O4/O5) is twisted away from the attached 2-pyrroline ring (C1···C4/N1) in all molecules: dihedral angles are 10.17 (1), 8.01 (1), 9.44 (1) and 8.87 (1)° in A, B, C and D, respectively. In molecule B, the methyl group of the methylsulfanyl functionality is disordered over two positions with occupancies of 0.15 (2):0.85 (2). In molecule D, the methylsulfanyl group attached to the 2-pyrroline ring is disordered over two sites, with occupancies of 0.797 (11):0.203 (11).

A weak intra-molecular O—H···O interaction is observed in molecules B and C (Table 1). The two hydroxy groups in each molecule are involved in inter-molecular O—H···O hydrogen bonding. The C—H···O interactions between molecules form a linear chain along the b axis. Intermolecular interactions O2A—H2A···O3A and O2D—H2D···O3D connect the inversion related dimers, forming a ring motif R22(10) (Fig. 5). The C14D—H14D···O4D inter-molecular interactions form a ring motif R22(16). These ring motifs are further connected by C—H···O interactions. The O3D—H3D···O3C interaction forms a linear chain along the b axis. The C—H···O interactions involving molecules A (Fig. 5) and B form a linear chain along the a axis. The C—H···O interactions between molecules C and D form a linear chain along the b axis. This combination of O—H···O and C—H··· O hydrogen bonds give a complex three-dimensional network for the crystal structure.

Related literature top

For the importance of pyrrolidine and pyrroline derivatives, see: Obniska et al. (2002); Stylianakis et al. (2003); Coldham & Hufton (2005); Kravchenko et al. (2005); Nair & Suja (2007); Pandey et al. (2006). For a related structure, see: Nagalakshmi et al. (2013). For ring conformation parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of (E)-4-methyl-N-[1-(methylthio)-2-nitrovinyl]aniline (1 mmol) with ninhydrin (2,2-dihydroxyindane-1,3-dione, 1 mmol) in presence of glacial AcOH (3–5 drops) was thoroughly ground in a pestle and mortar at room temperature for 2–10 min. The reaction progress was monitored by thin layer chromatography. After completion of the reaction, the reaction mixture was triturated with crushed ice, the resulting solid filtered off and washed with water to afford the pure product. The compound was further recrystallized from ethanol to obtain suitable crystals for X-ray analysis. Yield 96%; m.p. 471–474 K.

Refinement top

H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93 Å (aromatic CH) or 0.96 Å (methyl CH3) and O—H = 0.82 Å. isotropic displacement parameters for H atoms were defined as Uiso(H) = 1.2Ueq(C) for aromatic CH and Uiso(H) = 1.5Ueq(C, O) for CH3 and OH groups. Molecules B and C have disordered parts in their methylsulfanyl fragments. For molecule B, the methyl group is disordered over two positions, C2 and C5B, for which occupancies converged to 0.85 (2) and 0.15 (2), respectively. A combination of SIMU (similar Uij parameters for C2 and C5B) and DELU (rigid bonds for S2—C5B and S2—C2) restraints were applied (Sheldrick, 2008). In the case of molecule C the methylsulfanyl group is disordered over two positions, S3—C5C [occupancy: 0.797 (11)] and S3'—C1 [occupancy: 0.203 (11)]. A SADI (same distance) restraint was applied for bonds S3—C5C and S3'—C1.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme of molecule A. H atoms are omitted for clarity.
[Figure 2] Fig. 2. The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme of molecule B. H atoms are omitted for clarity.
[Figure 3] Fig. 3. The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme of molecule C. H atoms are omitted for clarity.
[Figure 4] Fig. 4. The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme of molecule D. H atoms are omitted for clarity.
[Figure 5] Fig. 5. The partial packing diagram showing O—H···O and C—H···O interactions in molecule A.
(3aR*,8bR*)-3a,8b-Dihydroxy-1-(4-methylphenyl)-2-methylsulfanyl-3-nitro-1,8b-dihydroindeno[1,2-b]pyrrol-4(3aH)-one top
Crystal data top
C19H16N2O5SZ = 8
Mr = 384.40F(000) = 1600
Triclinic, P1Dx = 1.457 Mg m−3
Hall symbol: -P 1Melting point: 471 K
a = 10.0830 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2775 (5) ÅCell parameters from 2000 reflections
c = 34.6579 (17) Åθ = 2–31°
α = 97.540 (3)°µ = 0.22 mm−1
β = 96.028 (3)°T = 293 K
γ = 97.138 (3)°Block, yellow
V = 3505.9 (3) Å30.21 × 0.19 × 0.18 mm
Data collection top
Bruker Kappa APEXII
diffractometer		13050 independent reflections
Radiation source: fine-focus sealed tube9856 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 0 pixels mm-1θmax = 25.5°, θmin = 0.6°
ω and φ scansh = −12→12
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −12→12
Tmin = 0.967, Tmax = 0.974l = −41→41
53951 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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0785P)2 + 4.0405P]
where P = (Fo2 + 2Fc2)/3
13050 reflections(Δ/σ)max = 0.001
1016 parametersΔρmax = 0.68 e Å−3
12 restraintsΔρmin = −0.30 e Å−3
0 constraints
Crystal data top
C19H16N2O5Sγ = 97.138 (3)°
Mr = 384.40V = 3505.9 (3) Å3
Triclinic, P1Z = 8
a = 10.0830 (5) ÅMo Kα radiation
b = 10.2775 (5) ŵ = 0.22 mm−1
c = 34.6579 (17) ÅT = 293 K
α = 97.540 (3)°0.21 × 0.19 × 0.18 mm
β = 96.028 (3)°
Data collection top
Bruker Kappa APEXII
diffractometer		13050 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		9856 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.974Rint = 0.041
53951 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06912 restraints
wR(F2) = 0.188H-atom parameters constrained
S = 1.06Δρmax = 0.68 e Å−3
13050 reflectionsΔρmin = −0.30 e Å−3
1016 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C5C−0.0868 (7)0.8339 (10)0.7819 (3)0.101 (3)0.797 (11)
H7−0.10130.79760.80560.152*0.797 (11)
H8−0.06650.76590.76260.152*0.797 (11)
H9−0.16660.86730.77220.152*0.797 (11)
S30.0486 (3)0.9635 (4)0.79199 (5)0.0627 (8)0.797 (11)
C1−0.074 (3)0.738 (2)0.7612 (9)0.108 (6)0.203 (11)
H16−0.12060.68490.77770.162*0.203 (11)
H17−0.00780.69110.74990.162*0.203 (11)
H18−0.13740.75700.74070.162*0.203 (11)
S3'0.0055 (12)0.8874 (18)0.7892 (2)0.072 (3)0.203 (11)
C1A0.3058 (3)0.6338 (3)0.48764 (9)0.0393 (7)
C1B−0.4152 (3)0.5374 (3)0.34840 (9)0.0408 (7)
C2A0.4370 (3)0.6700 (3)0.46797 (9)0.0408 (7)
C2B−0.5618 (4)0.4670 (4)0.34575 (10)0.0482 (8)
C3A0.5131 (3)0.7805 (3)0.49689 (9)0.0403 (7)
C3B−0.6424 (4)0.5603 (4)0.32766 (11)0.0558 (9)
C4A0.4468 (3)0.8042 (3)0.52945 (9)0.0369 (7)
C4B−0.5613 (4)0.6593 (4)0.31486 (10)0.0542 (9)
C5A0.4410 (4)0.8588 (4)0.60993 (11)0.0636 (11)
H10.44600.76550.60750.095*
H20.34880.87330.60990.095*
H30.49230.90270.63410.095*
C5B−0.540 (7)0.893 (5)0.282 (2)0.106 (6)0.15 (2)
H4−0.45350.86720.27710.159*0.15 (2)
H5−0.52840.96400.30300.159*0.15 (2)
H6−0.58050.92070.25840.159*0.15 (2)
C2−0.4941 (10)0.8501 (10)0.2651 (3)0.094 (3)0.85 (2)
H19−0.43000.91190.28310.142*0.85 (2)
H20−0.53290.89500.24510.142*0.85 (2)
H21−0.44970.78040.25330.142*0.85 (2)
C6A0.3863 (4)0.7211 (4)0.43000 (10)0.0467 (8)
C6B−0.5640 (4)0.3353 (4)0.31823 (11)0.0527 (9)
C7A0.2434 (4)0.7296 (4)0.43012 (10)0.0520 (9)
C7B−0.4258 (4)0.3248 (3)0.31042 (10)0.0469 (8)
C8A0.1947 (3)0.6753 (3)0.46124 (9)0.0444 (8)
C8B−0.3394 (3)0.4343 (3)0.32883 (9)0.0409 (7)
C9A0.0578 (4)0.6616 (4)0.46453 (12)0.0557 (9)
H9A0.02340.62430.48510.067*
C9B−0.2021 (4)0.4392 (4)0.32877 (10)0.0510 (9)
H9B−0.14310.51300.34130.061*
C10A−0.0254 (4)0.7053 (5)0.43626 (14)0.0724 (13)
H10A−0.11750.69690.43780.087*
C10B−0.1548 (5)0.3312 (4)0.30955 (12)0.0639 (11)
H10B−0.06250.33120.30970.077*
C11A0.0245 (5)0.7610 (5)0.40576 (14)0.0820 (15)
H11A−0.03440.79010.38730.098*
C11B−0.2432 (5)0.2229 (4)0.29000 (13)0.0687 (12)
H11B−0.20920.15230.27660.082*
C12A0.1586 (5)0.7740 (5)0.40212 (12)0.0701 (12)
H12A0.19220.81160.38150.084*
C12B−0.3785 (5)0.2177 (4)0.29002 (11)0.0597 (10)
H12B−0.43760.14500.27680.072*
C13A0.2158 (3)0.7433 (3)0.54657 (9)0.0383 (7)
C13B−0.3150 (4)0.7404 (3)0.32166 (10)0.0472 (8)
C14A0.1567 (3)0.8551 (3)0.54164 (10)0.0438 (8)
H14A0.19770.92040.52890.053*
C14B−0.2340 (5)0.7157 (4)0.29249 (12)0.0696 (12)
H14B−0.25530.63940.27410.084*
C15B−0.1219 (5)0.8049 (5)0.29082 (15)0.0800 (14)
H15B−0.06750.78650.27130.096*
C16A−0.0278 (3)0.7719 (4)0.57473 (10)0.0498 (8)
C16B−0.0875 (4)0.9188 (4)0.31660 (13)0.0625 (11)
C15A0.0347 (4)0.8687 (4)0.55607 (11)0.0498 (8)
H15A−0.00530.94420.55310.060*
C17A0.0366 (4)0.6634 (4)0.58047 (11)0.0524 (9)
H17A−0.00220.59960.59410.063*
C18A0.1573 (3)0.6482 (4)0.56627 (10)0.0468 (8)
H18A0.19880.57420.57000.056*
C17B−0.1718 (4)0.9422 (4)0.34562 (11)0.0576 (10)
H17B−0.15221.02000.36340.069*
C18B−0.2816 (4)0.8545 (4)0.34848 (10)0.0496 (8)
H18B−0.33420.87140.36860.060*
C19A−0.1661 (4)0.7826 (5)0.58720 (14)0.0724 (12)
H19A−0.23250.72210.56950.109*
H19B−0.18570.87150.58680.109*
H19C−0.16790.76080.61330.109*
C19B0.0391 (5)1.0120 (6)0.31561 (17)0.0941 (17)
H19D0.08050.98350.29280.141*
H19E0.10041.01200.33880.141*
H19F0.01731.09990.31460.141*
N1A0.3318 (2)0.7197 (3)0.52688 (7)0.0366 (6)
N1B−0.4299 (3)0.6477 (3)0.32421 (8)0.0446 (7)
N2A0.6351 (3)0.8495 (3)0.49127 (9)0.0523 (7)
N2B−0.7813 (4)0.5448 (5)0.32615 (11)0.0795 (12)
O1A0.4557 (3)0.7450 (3)0.40438 (7)0.0596 (7)
O1B−0.6620 (3)0.2552 (3)0.30708 (10)0.0868 (10)
O2A0.2734 (2)0.5022 (2)0.49147 (7)0.0484 (6)
H2A0.33520.47850.50490.073*
O3B−0.5922 (3)0.4394 (3)0.38327 (7)0.0563 (7)
H3B−0.67120.40600.38160.084*
O3A0.5110 (3)0.5622 (3)0.46113 (7)0.0504 (6)
H3A0.48850.52380.43870.076*
O2B−0.3484 (2)0.5870 (2)0.38529 (6)0.0448 (5)
H2B−0.38910.64300.39600.067*
O4A0.6824 (3)0.9511 (3)0.51445 (9)0.0707 (8)
O4B−0.8460 (3)0.6210 (5)0.30993 (11)0.1101 (14)
O5A0.6916 (3)0.8092 (3)0.46307 (9)0.0767 (9)
O5B−0.8371 (3)0.4541 (5)0.34225 (12)0.0987 (12)
S10.50842 (9)0.92446 (9)0.56943 (3)0.0504 (2)
S2−0.62570 (16)0.78016 (15)0.29113 (4)0.0902 (4)
C1D0.6383 (3)0.8124 (3)1.01223 (9)0.0405 (7)
C2D0.6902 (3)0.9583 (3)1.03256 (9)0.0422 (7)
C3D0.7771 (3)1.0098 (3)1.00404 (9)0.0417 (7)
C4D0.7760 (3)0.9169 (3)0.97153 (9)0.0379 (7)
C5D0.7641 (5)0.8362 (5)0.89118 (11)0.0664 (11)
H100.66990.83500.89350.100*
H110.78710.74830.89120.100*
H120.78330.86680.86710.100*
C6D0.7756 (3)0.9422 (4)1.07046 (10)0.0475 (8)
C7D0.7847 (4)0.8024 (4)1.07031 (10)0.0513 (9)
C8D0.7035 (3)0.7262 (4)1.03883 (10)0.0451 (8)
C9D0.6886 (4)0.5892 (4)1.03508 (12)0.0578 (10)
H9D0.63330.53711.01410.069*
C10D0.7581 (5)0.5323 (5)1.06343 (15)0.0710 (13)
H10D0.74950.44051.06140.085*
C11D0.8397 (5)0.6084 (5)1.09461 (15)0.0810 (15)
H11D0.88600.56711.11310.097*
C12D0.8538 (5)0.7432 (5)1.09896 (12)0.0701 (12)
H12D0.90780.79441.12030.084*
C13D0.7059 (3)0.6746 (3)0.95415 (9)0.0404 (7)
C14D0.8240 (3)0.6224 (3)0.95949 (10)0.0461 (8)
H14D0.90120.67540.97260.055*
C15D0.8284 (4)0.4909 (4)0.94538 (11)0.0512 (9)
H15D0.90880.45600.94930.061*
C16D0.7156 (4)0.4109 (4)0.92571 (11)0.0533 (9)
C17D0.5980 (4)0.4670 (4)0.91898 (11)0.0539 (9)
H17D0.52200.41520.90470.065*
C18D0.5921 (4)0.5971 (4)0.93292 (10)0.0477 (8)
H18D0.51280.63310.92820.057*
C19D0.7187 (5)0.2650 (4)0.91262 (15)0.0778 (13)
H19J0.67300.21370.92980.117*
H19K0.81040.24830.91350.117*
H19L0.67440.24040.88630.117*
N1D0.6938 (3)0.8045 (3)0.97352 (7)0.0379 (6)
N2D0.8481 (3)1.1362 (3)1.00990 (9)0.0531 (7)
O1D0.8237 (3)1.0340 (3)1.09637 (7)0.0595 (7)
O2D0.5001 (2)0.7761 (3)1.00695 (8)0.0506 (6)
H2D0.46460.82710.99420.076*
O3D0.5852 (2)1.0344 (3)1.03922 (7)0.0498 (6)
H3D0.56441.02951.06130.075*
O4D0.9295 (3)1.1659 (3)0.98715 (9)0.0699 (8)
O5D0.8301 (3)1.2162 (3)1.03853 (9)0.0744 (8)
S40.86152 (10)0.94568 (10)0.93187 (3)0.0532 (2)
C1C0.3302 (3)0.7827 (3)0.84914 (9)0.0427 (7)
C2C0.4071 (4)0.9207 (4)0.84560 (10)0.0465 (8)
C3C0.3014 (4)0.9892 (4)0.82676 (10)0.0531 (9)
C4C0.1834 (4)0.9043 (4)0.81611 (10)0.0535 (9)
C6C0.5135 (4)0.8886 (4)0.81767 (10)0.0505 (9)
C7C0.5025 (3)0.7446 (4)0.80862 (9)0.0457 (8)
C8C0.4066 (3)0.6835 (3)0.82799 (9)0.0436 (8)
C9C0.3899 (4)0.5475 (4)0.82721 (11)0.0593 (10)
H9C0.32540.50540.84040.071*
C10C0.4731 (5)0.4761 (5)0.80591 (13)0.0739 (12)
H10C0.46550.38470.80540.089*
C11C0.5665 (5)0.5370 (5)0.78551 (13)0.0716 (12)
H11C0.61910.48630.77090.086*
C12C0.5829 (4)0.6709 (5)0.78655 (11)0.0595 (10)
H12C0.64620.71240.77280.071*
C13C0.0970 (3)0.6701 (4)0.82203 (10)0.0499 (9)
C14C0.0850 (5)0.5777 (6)0.78867 (13)0.0871 (16)
H14C0.13850.59170.76890.105*
C15C−0.0070 (6)0.4646 (6)0.78502 (16)0.0958 (18)
H15C−0.01550.40320.76240.115*
C16C−0.0872 (5)0.4396 (5)0.81398 (15)0.0755 (13)
C17C−0.0760 (4)0.5352 (4)0.84590 (12)0.0609 (10)
H17C−0.13220.52350.86510.073*
C18C0.0158 (4)0.6483 (4)0.85049 (11)0.0529 (9)
H18C0.02280.71020.87300.063*
C19C−0.1815 (6)0.3122 (6)0.8111 (2)0.116 (2)
H19G−0.13680.25000.82420.174*
H19H−0.20780.27610.78410.174*
H19I−0.25990.32930.82330.174*
N1C0.1946 (3)0.7845 (3)0.82644 (8)0.0491 (7)
N2C0.3258 (4)1.1234 (4)0.82451 (11)0.0724 (10)
O1C0.5932 (3)0.9711 (3)0.80765 (10)0.0791 (9)
O2C0.3173 (2)0.7522 (2)0.88630 (6)0.0471 (6)
H2C0.27590.80570.89790.071*
O3C0.4712 (3)0.9862 (3)0.88256 (7)0.0550 (6)
H3C0.50821.05990.88010.083*
O4C0.2372 (4)1.1761 (4)0.80671 (12)0.1060 (13)
O5C0.4335 (4)1.1883 (3)0.84059 (12)0.0951 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C5C0.057 (4)0.118 (7)0.130 (7)−0.005 (5)−0.020 (4)0.070 (6)
S30.0530 (11)0.075 (2)0.0635 (9)0.0199 (12)−0.0072 (7)0.0244 (9)
C10.070 (9)0.125 (12)0.131 (12)0.003 (10)−0.026 (9)0.063 (10)
S3'0.061 (5)0.084 (9)0.071 (4)0.014 (6)−0.021 (3)0.029 (4)
C1A0.0416 (17)0.0419 (19)0.0355 (16)0.0149 (14)−0.0010 (13)0.0056 (13)
C1B0.0479 (18)0.0448 (19)0.0313 (16)0.0139 (14)0.0000 (13)0.0085 (13)
C2A0.0441 (18)0.049 (2)0.0339 (16)0.0247 (15)0.0046 (13)0.0079 (14)
C2B0.0484 (19)0.061 (2)0.0351 (17)0.0101 (16)0.0030 (14)0.0077 (15)
C3A0.0396 (17)0.0465 (19)0.0388 (17)0.0160 (14)0.0046 (13)0.0115 (14)
C3B0.047 (2)0.076 (3)0.046 (2)0.0205 (19)−0.0019 (16)0.0096 (18)
C4A0.0402 (17)0.0377 (17)0.0368 (16)0.0163 (13)0.0035 (13)0.0107 (13)
C4B0.069 (2)0.064 (2)0.0310 (17)0.026 (2)−0.0041 (16)0.0033 (16)
C5A0.076 (3)0.076 (3)0.0365 (19)0.015 (2)0.0023 (18)0.0005 (18)
C5B0.156 (11)0.073 (10)0.080 (11)0.032 (8)−0.044 (9)0.009 (9)
C20.147 (5)0.059 (5)0.070 (5)0.007 (4)−0.034 (3)0.028 (4)
C6A0.060 (2)0.050 (2)0.0351 (17)0.0277 (17)0.0061 (16)0.0086 (15)
C6B0.052 (2)0.059 (2)0.0442 (19)0.0011 (18)−0.0030 (16)0.0087 (16)
C7A0.061 (2)0.058 (2)0.0409 (19)0.0327 (18)−0.0027 (16)0.0042 (16)
C7B0.060 (2)0.045 (2)0.0383 (17)0.0141 (16)0.0007 (15)0.0113 (15)
C8A0.0475 (19)0.046 (2)0.0382 (17)0.0197 (15)−0.0056 (14)−0.0029 (14)
C8B0.0508 (19)0.0456 (19)0.0291 (15)0.0136 (15)0.0019 (13)0.0114 (13)
C9A0.050 (2)0.059 (2)0.055 (2)0.0192 (17)−0.0079 (17)−0.0032 (17)
C9B0.056 (2)0.057 (2)0.0424 (19)0.0153 (17)0.0079 (16)0.0082 (16)
C10A0.053 (2)0.076 (3)0.082 (3)0.031 (2)−0.020 (2)−0.012 (2)
C10B0.071 (3)0.073 (3)0.054 (2)0.031 (2)0.013 (2)0.008 (2)
C11A0.087 (3)0.100 (4)0.064 (3)0.057 (3)−0.018 (2)0.012 (3)
C11B0.093 (3)0.061 (3)0.060 (3)0.038 (2)0.015 (2)0.010 (2)
C12A0.085 (3)0.083 (3)0.051 (2)0.046 (2)−0.005 (2)0.018 (2)
C12B0.083 (3)0.047 (2)0.048 (2)0.014 (2)0.0016 (19)0.0047 (17)
C13A0.0371 (16)0.0443 (18)0.0353 (16)0.0112 (14)0.0052 (13)0.0061 (13)
C13B0.064 (2)0.0405 (19)0.0389 (18)0.0115 (16)0.0007 (16)0.0121 (14)
C14A0.0467 (19)0.0424 (19)0.0449 (18)0.0088 (15)0.0101 (15)0.0099 (14)
C14B0.109 (4)0.048 (2)0.054 (2)0.007 (2)0.029 (2)0.0027 (18)
C15B0.101 (4)0.071 (3)0.082 (3)0.018 (3)0.044 (3)0.031 (3)
C16A0.0438 (19)0.063 (2)0.0443 (19)0.0110 (17)0.0106 (15)0.0050 (16)
C16B0.069 (3)0.058 (3)0.064 (3)0.010 (2)0.001 (2)0.028 (2)
C15A0.048 (2)0.051 (2)0.054 (2)0.0198 (16)0.0075 (16)0.0055 (16)
C17A0.052 (2)0.058 (2)0.050 (2)0.0025 (17)0.0115 (16)0.0175 (17)
C18A0.0486 (19)0.047 (2)0.0482 (19)0.0121 (15)0.0079 (16)0.0146 (15)
C17B0.070 (3)0.050 (2)0.048 (2)0.0104 (19)−0.0110 (19)0.0051 (17)
C18B0.062 (2)0.051 (2)0.0365 (18)0.0173 (18)−0.0005 (16)0.0034 (15)
C19A0.050 (2)0.095 (3)0.075 (3)0.015 (2)0.020 (2)0.009 (2)
C19B0.085 (3)0.103 (4)0.098 (4)0.000 (3)0.003 (3)0.048 (3)
N1A0.0367 (14)0.0413 (15)0.0333 (13)0.0112 (11)0.0042 (11)0.0051 (11)
N1B0.0565 (17)0.0438 (16)0.0341 (14)0.0151 (13)−0.0032 (12)0.0069 (12)
N2A0.0452 (17)0.064 (2)0.0539 (18)0.0153 (15)0.0097 (15)0.0206 (16)
N2B0.052 (2)0.126 (4)0.062 (2)0.028 (2)−0.0060 (18)0.015 (2)
O1A0.0809 (18)0.0702 (18)0.0390 (13)0.0384 (14)0.0152 (13)0.0165 (12)
O1B0.069 (2)0.088 (2)0.089 (2)−0.0166 (18)0.0012 (17)−0.0097 (18)
O2A0.0506 (14)0.0431 (14)0.0499 (14)0.0124 (11)−0.0046 (11)0.0044 (10)
O3B0.0530 (14)0.0763 (18)0.0403 (13)0.0035 (13)0.0076 (11)0.0151 (12)
O3A0.0618 (15)0.0618 (16)0.0353 (12)0.0368 (13)0.0058 (11)0.0083 (11)
O2B0.0478 (13)0.0540 (14)0.0326 (11)0.0169 (11)−0.0012 (9)0.0018 (10)
O4A0.0630 (18)0.078 (2)0.0673 (18)−0.0103 (15)0.0089 (14)0.0168 (16)
O4B0.071 (2)0.181 (4)0.091 (3)0.062 (2)−0.0104 (19)0.040 (3)
O5A0.0607 (17)0.100 (2)0.079 (2)0.0227 (16)0.0366 (16)0.0176 (17)
O5B0.0479 (18)0.145 (4)0.106 (3)0.007 (2)0.0063 (18)0.036 (3)
S10.0530 (5)0.0503 (5)0.0445 (5)0.0062 (4)−0.0008 (4)0.0011 (4)
S20.1209 (11)0.0944 (10)0.0656 (7)0.0605 (8)−0.0119 (7)0.0250 (7)
C1D0.0443 (18)0.0436 (19)0.0372 (17)0.0137 (14)0.0080 (14)0.0093 (13)
C2D0.0489 (19)0.047 (2)0.0342 (16)0.0232 (15)0.0019 (14)0.0062 (14)
C3D0.0431 (18)0.0421 (19)0.0405 (17)0.0116 (14)−0.0010 (14)0.0083 (14)
C4D0.0376 (16)0.0435 (18)0.0362 (16)0.0175 (14)0.0035 (13)0.0093 (13)
C5D0.084 (3)0.085 (3)0.0343 (19)0.026 (2)0.0094 (19)0.0071 (19)
C6D0.0464 (19)0.066 (2)0.0342 (17)0.0251 (17)0.0038 (14)0.0061 (16)
C7D0.055 (2)0.067 (2)0.0415 (19)0.0314 (18)0.0075 (16)0.0180 (17)
C8D0.0483 (19)0.053 (2)0.0415 (18)0.0206 (16)0.0113 (15)0.0167 (15)
C9D0.065 (2)0.054 (2)0.065 (2)0.0217 (18)0.0222 (19)0.0232 (19)
C10D0.082 (3)0.064 (3)0.086 (3)0.038 (2)0.030 (3)0.040 (2)
C11D0.089 (3)0.094 (4)0.080 (3)0.053 (3)0.013 (3)0.046 (3)
C12D0.074 (3)0.095 (4)0.052 (2)0.045 (2)0.000 (2)0.022 (2)
C13D0.0440 (18)0.0398 (18)0.0384 (17)0.0104 (14)0.0043 (14)0.0052 (13)
C14D0.0437 (18)0.045 (2)0.0478 (19)0.0084 (15)0.0036 (15)0.0016 (15)
C15D0.051 (2)0.052 (2)0.053 (2)0.0197 (17)0.0053 (16)0.0043 (16)
C16D0.066 (2)0.044 (2)0.050 (2)0.0116 (18)0.0083 (18)0.0019 (16)
C17D0.054 (2)0.050 (2)0.052 (2)0.0018 (17)−0.0026 (17)0.0001 (17)
C18D0.0448 (19)0.049 (2)0.049 (2)0.0120 (15)−0.0014 (15)0.0043 (16)
C19D0.096 (3)0.048 (2)0.085 (3)0.014 (2)0.000 (3)−0.002 (2)
N1D0.0417 (14)0.0375 (15)0.0352 (14)0.0085 (11)0.0055 (11)0.0041 (11)
N2D0.0568 (19)0.0457 (18)0.0555 (19)0.0094 (14)−0.0030 (15)0.0089 (15)
O1D0.0647 (16)0.0750 (19)0.0386 (13)0.0288 (14)−0.0048 (12)−0.0017 (13)
O2D0.0445 (13)0.0559 (16)0.0567 (15)0.0154 (11)0.0105 (11)0.0164 (12)
O3D0.0569 (14)0.0604 (16)0.0372 (12)0.0334 (12)0.0022 (11)0.0046 (11)
O4D0.0740 (19)0.0618 (18)0.0677 (18)−0.0120 (15)0.0015 (15)0.0127 (14)
O5D0.096 (2)0.0473 (16)0.074 (2)0.0147 (15)0.0043 (17)−0.0111 (14)
S40.0569 (5)0.0618 (6)0.0452 (5)0.0105 (4)0.0132 (4)0.0156 (4)
C1C0.0469 (18)0.053 (2)0.0286 (15)0.0117 (15)−0.0013 (13)0.0077 (14)
C2C0.055 (2)0.048 (2)0.0377 (17)0.0136 (16)−0.0001 (15)0.0109 (14)
C3C0.065 (2)0.054 (2)0.0433 (19)0.0186 (19)0.0000 (17)0.0135 (16)
C4C0.062 (2)0.071 (3)0.0363 (18)0.033 (2)0.0064 (16)0.0172 (17)
C6C0.053 (2)0.060 (2)0.0411 (19)0.0109 (18)0.0034 (16)0.0167 (16)
C7C0.0479 (19)0.056 (2)0.0331 (16)0.0120 (16)−0.0023 (14)0.0062 (14)
C8C0.0475 (19)0.047 (2)0.0354 (17)0.0100 (15)−0.0030 (14)0.0053 (14)
C9C0.075 (3)0.056 (2)0.046 (2)0.010 (2)0.0071 (19)0.0058 (17)
C10C0.102 (4)0.061 (3)0.061 (3)0.025 (2)0.011 (3)0.004 (2)
C11C0.086 (3)0.075 (3)0.057 (2)0.039 (2)0.011 (2)−0.003 (2)
C12C0.057 (2)0.078 (3)0.045 (2)0.019 (2)0.0059 (17)0.0065 (19)
C13C0.0452 (19)0.070 (2)0.0357 (18)0.0179 (17)−0.0005 (15)0.0069 (16)
C14C0.067 (3)0.130 (5)0.051 (3)−0.007 (3)0.009 (2)−0.017 (3)
C15C0.086 (4)0.106 (4)0.075 (3)−0.006 (3)−0.002 (3)−0.033 (3)
C16C0.060 (3)0.077 (3)0.081 (3)0.002 (2)−0.018 (2)0.009 (3)
C17C0.054 (2)0.080 (3)0.052 (2)0.010 (2)0.0001 (18)0.026 (2)
C18C0.055 (2)0.063 (2)0.0428 (19)0.0152 (18)0.0033 (16)0.0103 (17)
C19C0.105 (4)0.089 (4)0.136 (6)−0.017 (3)−0.033 (4)0.019 (4)
N1C0.0429 (16)0.067 (2)0.0382 (15)0.0101 (14)0.0003 (12)0.0143 (14)
N2C0.093 (3)0.061 (2)0.071 (2)0.029 (2)0.004 (2)0.0287 (19)
O1C0.083 (2)0.073 (2)0.088 (2)0.0013 (17)0.0293 (18)0.0309 (17)
O2C0.0581 (14)0.0550 (15)0.0312 (11)0.0168 (11)0.0055 (10)0.0096 (10)
O3C0.0694 (16)0.0526 (15)0.0407 (13)0.0047 (12)−0.0028 (12)0.0089 (11)
O4C0.131 (3)0.083 (2)0.111 (3)0.041 (2)−0.018 (2)0.042 (2)
O5C0.108 (3)0.061 (2)0.111 (3)−0.0012 (19)−0.017 (2)0.0289 (19)
Geometric parameters (Å, º) top
C5C—S31.757 (8)N2A—O4A1.241 (4)
S3—C4C1.737 (4)N2B—O4B1.233 (5)
C1—S3'1.755 (10)N2B—O5B1.253 (5)
S3'—C4C1.909 (10)C1D—O2D1.384 (4)
C1A—O2A1.379 (4)C1D—N1D1.503 (4)
C1A—N1A1.500 (4)C1D—C8D1.516 (4)
C1A—C8A1.509 (4)C1D—C2D1.571 (5)
C1A—C2A1.578 (5)C2D—O3D1.412 (4)
C1B—O2B1.382 (4)C2D—C3D1.494 (5)
C1B—N1B1.508 (4)C2D—C6D1.533 (4)
C1B—C8B1.513 (5)C3D—C4D1.376 (5)
C1B—C2B1.551 (5)C3D—N2D1.382 (5)
C2A—O3A1.419 (4)C4D—N1D1.349 (4)
C2A—C3A1.485 (5)C4D—S41.736 (3)
C2A—C6A1.541 (4)C5D—S41.800 (4)
C2B—O3B1.423 (4)C6D—O1D1.226 (4)
C2B—C3B1.489 (5)C6D—C7D1.451 (5)
C2B—C6B1.547 (5)C7D—C8D1.379 (5)
C3A—C4A1.381 (4)C7D—C12D1.400 (5)
C3A—N2A1.387 (4)C8D—C9D1.384 (5)
C3B—C4B1.375 (6)C9D—C10D1.381 (6)
C3B—N2B1.384 (5)C10D—C11D1.374 (7)
C4A—N1A1.348 (4)C11D—C12D1.361 (7)
C4A—S11.735 (3)C13D—C14D1.371 (5)
C4B—N1B1.354 (5)C13D—C18D1.391 (5)
C4B—S21.731 (4)C13D—N1D1.439 (4)
C5A—S11.795 (4)C14D—C15D1.383 (5)
C5B—S21.45 (6)C15D—C16D1.376 (5)
C2—S21.809 (10)C16D—C17D1.392 (5)
C6A—O1A1.218 (4)C16D—C19D1.514 (6)
C6A—C7A1.455 (5)C17D—C18D1.372 (5)
C6B—O1B1.199 (4)N2D—O4D1.235 (4)
C6B—C7B1.462 (5)N2D—O5D1.247 (4)
C7A—C8A1.385 (5)C1C—O2C1.380 (4)
C7A—C12A1.385 (5)C1C—N1C1.508 (4)
C7B—C8B1.372 (5)C1C—C8C1.512 (5)
C7B—C12B1.391 (5)C1C—C2C1.556 (5)
C8A—C9A1.389 (5)C2C—O3C1.415 (4)
C8B—C9B1.379 (5)C2C—C3C1.489 (5)
C9A—C10A1.379 (6)C2C—C6C1.556 (5)
C9B—C10B1.381 (5)C3C—C4C1.371 (6)
C10A—C11A1.378 (7)C3C—N2C1.384 (5)
C10B—C11B1.386 (6)C4C—N1C1.341 (5)
C11A—C12A1.364 (7)C6C—O1C1.204 (4)
C11B—C12B1.359 (6)C6C—C7C1.460 (5)
C13A—C18A1.373 (5)C7C—C8C1.370 (5)
C13A—C14A1.380 (5)C7C—C12C1.395 (5)
C13A—N1A1.445 (4)C8C—C9C1.384 (5)
C13B—C18B1.380 (5)C9C—C10C1.389 (6)
C13B—C14B1.382 (5)C10C—C11C1.374 (7)
C13B—N1B1.424 (5)C11C—C12C1.361 (6)
C14A—C15A1.391 (5)C13C—C18C1.370 (5)
C14B—C15B1.375 (6)C13C—C14C1.381 (6)
C15B—C16B1.360 (7)C13C—N1C1.417 (5)
C16A—C15A1.380 (5)C14C—C15C1.377 (7)
C16A—C17A1.385 (5)C15C—C16C1.384 (7)
C16A—C19A1.515 (5)C16C—C17C1.365 (7)
C16B—C17B1.400 (6)C16C—C19C1.504 (7)
C16B—C19B1.504 (6)C17C—C18C1.372 (6)
C17A—C18A1.378 (5)N2C—O5C1.237 (5)
C17B—C18B1.358 (5)N2C—O4C1.251 (5)
N2A—O5A1.232 (4)
C4C—S3—C5C107.6 (3)C4B—S2—C2106.8 (3)
C1—S3'—C4C122.1 (12)O2D—C1D—N1D111.0 (3)
O2A—C1A—N1A111.3 (2)O2D—C1D—C8D109.7 (3)
O2A—C1A—C8A109.3 (3)N1D—C1D—C8D111.5 (3)
N1A—C1A—C8A111.8 (3)O2D—C1D—C2D115.9 (3)
O2A—C1A—C2A116.1 (3)N1D—C1D—C2D104.0 (2)
N1A—C1A—C2A103.9 (2)C8D—C1D—C2D104.6 (3)
C8A—C1A—C2A104.3 (3)O3D—C2D—C3D112.4 (3)
O2B—C1B—N1B110.6 (3)O3D—C2D—C6D113.1 (3)
O2B—C1B—C8B109.1 (3)C3D—C2D—C6D110.8 (3)
N1B—C1B—C8B111.4 (3)O3D—C2D—C1D113.3 (3)
O2B—C1B—C2B117.7 (3)C3D—C2D—C1D102.1 (3)
N1B—C1B—C2B103.0 (3)C6D—C2D—C1D104.4 (3)
C8B—C1B—C2B104.9 (3)C4D—C3D—N2D124.9 (3)
O3A—C2A—C3A112.3 (3)C4D—C3D—C2D111.7 (3)
O3A—C2A—C6A113.0 (3)N2D—C3D—C2D123.4 (3)
C3A—C2A—C6A110.6 (3)N1D—C4D—C3D111.3 (3)
O3A—C2A—C1A113.2 (3)N1D—C4D—S4124.7 (2)
C3A—C2A—C1A102.3 (2)C3D—C4D—S4123.8 (3)
C6A—C2A—C1A104.5 (3)O1D—C6D—C7D127.3 (3)
O3B—C2B—C3B115.9 (3)O1D—C6D—C2D124.3 (3)
O3B—C2B—C6B109.5 (3)C7D—C6D—C2D108.4 (3)
C3B—C2B—C6B112.7 (3)C8D—C7D—C12D120.9 (4)
O3B—C2B—C1B110.7 (3)C8D—C7D—C6D111.2 (3)
C3B—C2B—C1B102.9 (3)C12D—C7D—C6D127.7 (4)
C6B—C2B—C1B104.3 (3)C7D—C8D—C9D120.4 (3)
C4A—C3A—N2A125.3 (3)C7D—C8D—C1D111.1 (3)
C4A—C3A—C2A111.3 (3)C9D—C8D—C1D128.5 (3)
N2A—C3A—C2A123.4 (3)C10D—C9D—C8D118.0 (4)
C4B—C3B—N2B127.3 (4)C11D—C10D—C9D121.5 (4)
C4B—C3B—C2B111.5 (3)C12D—C11D—C10D121.1 (4)
N2B—C3B—C2B121.2 (4)C11D—C12D—C7D118.1 (4)
N1A—C4A—C3A111.7 (3)C14D—C13D—C18D120.0 (3)
N1A—C4A—S1124.5 (2)C14D—C13D—N1D120.8 (3)
C3A—C4A—S1123.7 (3)C18D—C13D—N1D119.0 (3)
N1B—C4B—C3B110.3 (3)C13D—C14D—C15D120.0 (3)
N1B—C4B—S2127.2 (3)C16D—C15D—C14D120.9 (3)
C3B—C4B—S2122.4 (3)C15D—C16D—C17D118.3 (3)
O1A—C6A—C7A127.5 (3)C15D—C16D—C19D120.7 (4)
O1A—C6A—C2A124.4 (3)C17D—C16D—C19D121.0 (4)
C7A—C6A—C2A108.0 (3)C18D—C17D—C16D121.3 (3)
O1B—C6B—C7B127.3 (4)C17D—C18D—C13D119.3 (3)
O1B—C6B—C2B125.0 (4)C4D—N1D—C13D125.5 (3)
C7B—C6B—C2B107.6 (3)C4D—N1D—C1D110.6 (3)
C8A—C7A—C12A121.5 (4)C13D—N1D—C1D117.1 (2)
C8A—C7A—C6A110.9 (3)O4D—N2D—O5D121.9 (3)
C12A—C7A—C6A127.4 (4)O4D—N2D—C3D119.2 (3)
C8B—C7B—C12B121.4 (4)O5D—N2D—C3D118.9 (3)
C8B—C7B—C6B110.9 (3)C4D—S4—C5D103.93 (19)
C12B—C7B—C6B127.5 (4)O2C—C1C—N1C111.3 (3)
C7A—C8A—C9A120.1 (3)O2C—C1C—C8C109.1 (3)
C7A—C8A—C1A111.8 (3)N1C—C1C—C8C110.9 (3)
C9A—C8A—C1A128.1 (3)O2C—C1C—C2C117.8 (3)
C7B—C8B—C9B120.6 (3)N1C—C1C—C2C102.4 (3)
C7B—C8B—C1B111.3 (3)C8C—C1C—C2C105.0 (3)
C9B—C8B—C1B128.1 (3)O3C—C2C—C3C115.0 (3)
C10A—C9A—C8A117.7 (4)O3C—C2C—C6C110.4 (3)
C8B—C9B—C10B118.0 (4)C3C—C2C—C6C111.7 (3)
C11A—C10A—C9A121.7 (4)O3C—C2C—C1C111.2 (3)
C9B—C10B—C11B120.8 (4)C3C—C2C—C1C103.6 (3)
C12A—C11A—C10A121.1 (4)C6C—C2C—C1C104.2 (3)
C12B—C11B—C10B121.3 (4)C4C—C3C—N2C128.4 (4)
C11A—C12A—C7A117.9 (4)C4C—C3C—C2C110.6 (3)
C11B—C12B—C7B117.8 (4)N2C—C3C—C2C120.7 (4)
C18A—C13A—C14A120.8 (3)N1C—C4C—C3C111.3 (3)
C18A—C13A—N1A119.8 (3)N1C—C4C—S3130.8 (4)
C14A—C13A—N1A119.1 (3)C3C—C4C—S3117.9 (3)
C18B—C13B—C14B119.1 (4)N1C—C4C—S3'104.9 (6)
C18B—C13B—N1B120.7 (3)C3C—C4C—S3'143.7 (6)
C14B—C13B—N1B120.1 (3)O1C—C6C—C7C128.1 (4)
C13A—C14A—C15A119.0 (3)O1C—C6C—C2C124.1 (4)
C15B—C14B—C13B119.5 (4)C7C—C6C—C2C107.7 (3)
C16B—C15B—C14B122.6 (4)C8C—C7C—C12C120.9 (4)
C15A—C16A—C17A118.5 (3)C8C—C7C—C6C111.1 (3)
C15A—C16A—C19A120.3 (4)C12C—C7C—C6C127.8 (4)
C17A—C16A—C19A121.1 (4)C7C—C8C—C9C120.8 (3)
C15B—C16B—C17B116.8 (4)C7C—C8C—C1C111.5 (3)
C15B—C16B—C19B121.9 (5)C9C—C8C—C1C127.7 (3)
C17B—C16B—C19B121.2 (5)C8C—C9C—C10C117.5 (4)
C16A—C15A—C14A121.0 (3)C11C—C10C—C9C121.7 (4)
C18A—C17A—C16A121.2 (3)C12C—C11C—C10C120.6 (4)
C13A—C18A—C17A119.5 (3)C11C—C12C—C7C118.6 (4)
C18B—C17B—C16B121.9 (4)C18C—C13C—C14C119.3 (4)
C17B—C18B—C13B120.1 (4)C18C—C13C—N1C121.3 (3)
C4A—N1A—C13A126.1 (3)C14C—C13C—N1C119.4 (4)
C4A—N1A—C1A110.4 (2)C15C—C14C—C13C119.2 (4)
C13A—N1A—C1A116.9 (2)C14C—C15C—C16C122.1 (5)
C4B—N1B—C13B127.9 (3)C17C—C16C—C15C117.0 (4)
C4B—N1B—C1B111.0 (3)C17C—C16C—C19C120.9 (5)
C13B—N1B—C1B119.4 (3)C15C—C16C—C19C122.1 (5)
O5A—N2A—O4A122.3 (3)C16C—C17C—C18C122.1 (4)
O5A—N2A—C3A119.0 (3)C13C—C18C—C17C120.2 (4)
O4A—N2A—C3A118.7 (3)C4C—N1C—C13C129.8 (3)
O4B—N2B—O5B122.0 (4)C4C—N1C—C1C111.4 (3)
O4B—N2B—C3B119.8 (5)C13C—N1C—C1C118.6 (3)
O5B—N2B—C3B118.1 (4)O5C—N2C—O4C121.8 (4)
C4A—S1—C5A103.90 (18)O5C—N2C—C3C119.3 (4)
C5B—S2—C4B122 (2)O4C—N2C—C3C119.0 (4)
O2A—C1A—C2A—O3A−6.8 (4)O2D—C1D—C2D—C3D−126.5 (3)
N1A—C1A—C2A—O3A115.7 (3)N1D—C1D—C2D—C3D−4.4 (3)
C8A—C1A—C2A—O3A−127.1 (3)C8D—C1D—C2D—C3D112.7 (3)
O2A—C1A—C2A—C3A−127.9 (3)O2D—C1D—C2D—C6D118.1 (3)
N1A—C1A—C2A—C3A−5.5 (3)N1D—C1D—C2D—C6D−119.9 (3)
C8A—C1A—C2A—C3A111.7 (3)C8D—C1D—C2D—C6D−2.8 (3)
O2A—C1A—C2A—C6A116.7 (3)O3D—C2D—C3D—C4D−119.6 (3)
N1A—C1A—C2A—C6A−120.9 (3)C6D—C2D—C3D—C4D112.8 (3)
C8A—C1A—C2A—C6A−3.7 (3)C1D—C2D—C3D—C4D2.1 (3)
O2B—C1B—C2B—O3B−13.3 (4)O3D—C2D—C3D—N2D59.7 (4)
N1B—C1B—C2B—O3B−135.2 (3)C6D—C2D—C3D—N2D−67.9 (4)
C8B—C1B—C2B—O3B108.1 (3)C1D—C2D—C3D—N2D−178.6 (3)
O2B—C1B—C2B—C3B111.2 (3)N2D—C3D—C4D—N1D−177.8 (3)
N1B—C1B—C2B—C3B−10.8 (3)C2D—C3D—C4D—N1D1.5 (4)
C8B—C1B—C2B—C3B−127.4 (3)N2D—C3D—C4D—S4−1.5 (5)
O2B—C1B—C2B—C6B−131.0 (3)C2D—C3D—C4D—S4177.8 (2)
N1B—C1B—C2B—C6B107.1 (3)O3D—C2D—C6D—O1D−49.3 (5)
C8B—C1B—C2B—C6B−9.6 (3)C3D—C2D—C6D—O1D77.9 (4)
O3A—C2A—C3A—C4A−118.8 (3)C1D—C2D—C6D—O1D−172.9 (3)
C6A—C2A—C3A—C4A113.9 (3)O3D—C2D—C6D—C7D129.0 (3)
C1A—C2A—C3A—C4A3.0 (3)C3D—C2D—C6D—C7D−103.8 (3)
O3A—C2A—C3A—N2A61.1 (4)C1D—C2D—C6D—C7D5.4 (4)
C6A—C2A—C3A—N2A−66.2 (4)O1D—C6D—C7D—C8D171.8 (4)
C1A—C2A—C3A—N2A−177.1 (3)C2D—C6D—C7D—C8D−6.4 (4)
O3B—C2B—C3B—C4B130.0 (3)O1D—C6D—C7D—C12D−2.4 (6)
C6B—C2B—C3B—C4B−102.7 (4)C2D—C6D—C7D—C12D179.4 (4)
C1B—C2B—C3B—C4B9.1 (4)C12D—C7D—C8D—C9D0.2 (5)
O3B—C2B—C3B—N2B−48.1 (5)C6D—C7D—C8D—C9D−174.4 (3)
C6B—C2B—C3B—N2B79.1 (4)C12D—C7D—C8D—C1D179.2 (3)
C1B—C2B—C3B—N2B−169.1 (3)C6D—C7D—C8D—C1D4.6 (4)
N2A—C3A—C4A—N1A−178.8 (3)O2D—C1D—C8D—C7D−125.8 (3)
C2A—C3A—C4A—N1A1.1 (4)N1D—C1D—C8D—C7D110.8 (3)
N2A—C3A—C4A—S1−1.1 (5)C2D—C1D—C8D—C7D−0.9 (4)
C2A—C3A—C4A—S1178.8 (2)O2D—C1D—C8D—C9D53.1 (5)
N2B—C3B—C4B—N1B174.8 (4)N1D—C1D—C8D—C9D−70.2 (4)
C2B—C3B—C4B—N1B−3.1 (4)C2D—C1D—C8D—C9D178.0 (3)
N2B—C3B—C4B—S2−4.1 (6)C7D—C8D—C9D—C10D−0.6 (5)
C2B—C3B—C4B—S2177.9 (3)C1D—C8D—C9D—C10D−179.5 (3)
O3A—C2A—C6A—O1A−47.8 (5)C8D—C9D—C10D—C11D0.2 (6)
C3A—C2A—C6A—O1A79.2 (4)C9D—C10D—C11D—C12D0.7 (7)
C1A—C2A—C6A—O1A−171.3 (3)C10D—C11D—C12D—C7D−1.2 (7)
O3A—C2A—C6A—C7A130.0 (3)C8D—C7D—C12D—C11D0.7 (6)
C3A—C2A—C6A—C7A−103.0 (3)C6D—C7D—C12D—C11D174.4 (4)
C1A—C2A—C6A—C7A6.5 (4)C18D—C13D—C14D—C15D−3.1 (5)
O3B—C2B—C6B—O1B65.6 (5)N1D—C13D—C14D—C15D170.6 (3)
C3B—C2B—C6B—O1B−65.0 (5)C13D—C14D—C15D—C16D0.4 (6)
C1B—C2B—C6B—O1B−175.9 (4)C14D—C15D—C16D—C17D2.5 (6)
O3B—C2B—C6B—C7B−111.5 (3)C14D—C15D—C16D—C19D−176.1 (4)
C3B—C2B—C6B—C7B117.9 (3)C15D—C16D—C17D—C18D−2.8 (6)
C1B—C2B—C6B—C7B7.0 (4)C19D—C16D—C17D—C18D175.8 (4)
O1A—C6A—C7A—C8A170.6 (4)C16D—C17D—C18D—C13D0.1 (6)
C2A—C6A—C7A—C8A−7.1 (4)C14D—C13D—C18D—C17D2.8 (5)
O1A—C6A—C7A—C12A−4.1 (7)N1D—C13D—C18D—C17D−171.0 (3)
C2A—C6A—C7A—C12A178.2 (4)C3D—C4D—N1D—C13D−154.6 (3)
O1B—C6B—C7B—C8B−178.4 (4)S4—C4D—N1D—C13D29.2 (4)
C2B—C6B—C7B—C8B−1.4 (4)C3D—C4D—N1D—C1D−4.7 (4)
O1B—C6B—C7B—C12B−3.2 (6)S4—C4D—N1D—C1D179.1 (2)
C2B—C6B—C7B—C12B173.9 (3)C14D—C13D—N1D—C4D54.7 (4)
C12A—C7A—C8A—C9A1.3 (6)C18D—C13D—N1D—C4D−131.5 (3)
C6A—C7A—C8A—C9A−173.7 (3)C14D—C13D—N1D—C1D−93.5 (4)
C12A—C7A—C8A—C1A179.8 (4)C18D—C13D—N1D—C1D80.3 (4)
C6A—C7A—C8A—C1A4.7 (4)O2D—C1D—N1D—C4D130.9 (3)
O2A—C1A—C8A—C7A−125.2 (3)C8D—C1D—N1D—C4D−106.5 (3)
N1A—C1A—C8A—C7A111.2 (3)C2D—C1D—N1D—C4D5.7 (3)
C2A—C1A—C8A—C7A−0.4 (4)O2D—C1D—N1D—C13D−76.4 (3)
O2A—C1A—C8A—C9A53.1 (4)C8D—C1D—N1D—C13D46.3 (4)
N1A—C1A—C8A—C9A−70.6 (4)C2D—C1D—N1D—C13D158.4 (3)
C2A—C1A—C8A—C9A177.9 (3)C4D—C3D—N2D—O4D−9.0 (5)
C12B—C7B—C8B—C9B−2.3 (5)C2D—C3D—N2D—O4D171.8 (3)
C6B—C7B—C8B—C9B173.3 (3)C4D—C3D—N2D—O5D172.5 (3)
C12B—C7B—C8B—C1B179.2 (3)C2D—C3D—N2D—O5D−6.7 (5)
C6B—C7B—C8B—C1B−5.2 (4)N1D—C4D—S4—C5D23.7 (3)
O2B—C1B—C8B—C7B136.3 (3)C3D—C4D—S4—C5D−152.1 (3)
N1B—C1B—C8B—C7B−101.3 (3)O2C—C1C—C2C—O3C9.4 (4)
C2B—C1B—C8B—C7B9.4 (3)N1C—C1C—C2C—O3C131.9 (3)
O2B—C1B—C8B—C9B−42.0 (4)C8C—C1C—C2C—O3C−112.2 (3)
N1B—C1B—C8B—C9B80.4 (4)O2C—C1C—C2C—C3C−114.7 (3)
C2B—C1B—C8B—C9B−168.9 (3)N1C—C1C—C2C—C3C7.8 (3)
C7A—C8A—C9A—C10A−0.8 (5)C8C—C1C—C2C—C3C123.7 (3)
C1A—C8A—C9A—C10A−178.9 (4)O2C—C1C—C2C—C6C128.4 (3)
C7B—C8B—C9B—C10B0.3 (5)N1C—C1C—C2C—C6C−109.2 (3)
C1B—C8B—C9B—C10B178.5 (3)C8C—C1C—C2C—C6C6.8 (3)
C8A—C9A—C10A—C11A−0.2 (6)O3C—C2C—C3C—C4C−127.7 (3)
C8B—C9B—C10B—C11B1.8 (6)C6C—C2C—C3C—C4C105.4 (4)
C9A—C10A—C11A—C12A0.6 (7)C1C—C2C—C3C—C4C−6.1 (4)
C9B—C10B—C11B—C12B−1.9 (6)O3C—C2C—C3C—N2C47.7 (5)
C10A—C11A—C12A—C7A−0.1 (7)C6C—C2C—C3C—N2C−79.2 (4)
C8A—C7A—C12A—C11A−0.9 (6)C1C—C2C—C3C—N2C169.3 (3)
C6A—C7A—C12A—C11A173.3 (4)N2C—C3C—C4C—N1C−173.4 (4)
C10B—C11B—C12B—C7B−0.1 (6)C2C—C3C—C4C—N1C1.6 (4)
C8B—C7B—C12B—C11B2.2 (5)N2C—C3C—C4C—S37.3 (6)
C6B—C7B—C12B—C11B−172.6 (4)C2C—C3C—C4C—S3−177.8 (3)
C18A—C13A—C14A—C15A−1.7 (5)N2C—C3C—C4C—S3'10.8 (9)
N1A—C13A—C14A—C15A171.2 (3)C2C—C3C—C4C—S3'−174.2 (5)
C18B—C13B—C14B—C15B0.2 (6)C5C—S3—C4C—N1C0.5 (5)
N1B—C13B—C14B—C15B−178.8 (4)C5C—S3—C4C—C3C179.7 (4)
C13B—C14B—C15B—C16B−1.0 (7)C5C—S3—C4C—S3'4.6 (7)
C14B—C15B—C16B—C17B0.3 (7)C1—S3'—C4C—N1C−32.4 (16)
C14B—C15B—C16B—C19B176.9 (5)C1—S3'—C4C—C3C143.5 (17)
C17A—C16A—C15A—C14A3.0 (6)C1—S3'—C4C—S3150.8 (18)
C19A—C16A—C15A—C14A−174.8 (3)O3C—C2C—C6C—O1C−60.7 (5)
C13A—C14A—C15A—C16A−0.6 (5)C3C—C2C—C6C—O1C68.7 (5)
C15A—C16A—C17A—C18A−3.2 (6)C1C—C2C—C6C—O1C179.9 (3)
C19A—C16A—C17A—C18A174.6 (4)O3C—C2C—C6C—C7C116.0 (3)
C14A—C13A—C18A—C17A1.5 (5)C3C—C2C—C6C—C7C−114.6 (3)
N1A—C13A—C18A—C17A−171.4 (3)C1C—C2C—C6C—C7C−3.4 (3)
C16A—C17A—C18A—C13A0.9 (6)O1C—C6C—C7C—C8C174.8 (4)
C15B—C16B—C17B—C18B1.2 (6)C2C—C6C—C7C—C8C−1.7 (4)
C19B—C16B—C17B—C18B−175.5 (4)O1C—C6C—C7C—C12C0.5 (6)
C16B—C17B—C18B—C13B−2.0 (6)C2C—C6C—C7C—C12C−176.0 (3)
C14B—C13B—C18B—C17B1.2 (5)C12C—C7C—C8C—C9C2.1 (5)
N1B—C13B—C18B—C17B−179.8 (3)C6C—C7C—C8C—C9C−172.6 (3)
C3A—C4A—N1A—C13A−155.3 (3)C12C—C7C—C8C—C1C−178.8 (3)
S1—C4A—N1A—C13A27.0 (4)C6C—C7C—C8C—C1C6.5 (4)
C3A—C4A—N1A—C1A−5.1 (3)O2C—C1C—C8C—C7C−135.5 (3)
S1—C4A—N1A—C1A177.2 (2)N1C—C1C—C8C—C7C101.5 (3)
C18A—C13A—N1A—C4A−132.1 (3)C2C—C1C—C8C—C7C−8.4 (3)
C14A—C13A—N1A—C4A54.9 (4)O2C—C1C—C8C—C9C43.5 (5)
C18A—C13A—N1A—C1A79.4 (4)N1C—C1C—C8C—C9C−79.5 (4)
C14A—C13A—N1A—C1A−93.6 (4)C2C—C1C—C8C—C9C170.6 (3)
O2A—C1A—N1A—C4A132.2 (3)C7C—C8C—C9C—C10C−0.4 (6)
C8A—C1A—N1A—C4A−105.3 (3)C1C—C8C—C9C—C10C−179.4 (4)
C2A—C1A—N1A—C4A6.6 (3)C8C—C9C—C10C—C11C−1.6 (7)
O2A—C1A—N1A—C13A−74.6 (3)C9C—C10C—C11C—C12C1.9 (7)
C8A—C1A—N1A—C13A48.0 (4)C10C—C11C—C12C—C7C−0.2 (6)
C2A—C1A—N1A—C13A159.8 (2)C8C—C7C—C12C—C11C−1.8 (5)
C3B—C4B—N1B—C13B−169.6 (3)C6C—C7C—C12C—C11C172.0 (4)
S2—C4B—N1B—C13B9.3 (5)C18C—C13C—C14C—C15C−1.0 (7)
C3B—C4B—N1B—C1B−4.7 (4)N1C—C13C—C14C—C15C178.0 (5)
S2—C4B—N1B—C1B174.2 (3)C13C—C14C—C15C—C16C−0.7 (9)
C18B—C13B—N1B—C4B74.3 (4)C14C—C15C—C16C—C17C3.0 (8)
C14B—C13B—N1B—C4B−106.8 (5)C14C—C15C—C16C—C19C−176.1 (6)
C18B—C13B—N1B—C1B−89.5 (4)C15C—C16C—C17C—C18C−3.6 (7)
C14B—C13B—N1B—C1B89.4 (4)C19C—C16C—C17C—C18C175.4 (4)
O2B—C1B—N1B—C4B−116.6 (3)C14C—C13C—C18C—C17C0.4 (6)
C8B—C1B—N1B—C4B121.9 (3)N1C—C13C—C18C—C17C−178.6 (3)
C2B—C1B—N1B—C4B10.0 (3)C16C—C17C—C18C—C13C2.0 (6)
O2B—C1B—N1B—C13B49.7 (4)C3C—C4C—N1C—C13C178.1 (3)
C8B—C1B—N1B—C13B−71.8 (4)S3—C4C—N1C—C13C−2.7 (6)
C2B—C1B—N1B—C13B176.3 (3)S3'—C4C—N1C—C13C−4.5 (5)
C4A—C3A—N2A—O5A171.8 (3)C3C—C4C—N1C—C1C4.1 (4)
C2A—C3A—N2A—O5A−8.1 (5)S3—C4C—N1C—C1C−176.7 (3)
C4A—C3A—N2A—O4A−9.6 (5)S3'—C4C—N1C—C1C−178.5 (3)
C2A—C3A—N2A—O4A170.5 (3)C18C—C13C—N1C—C4C−89.6 (5)
C4B—C3B—N2B—O4B4.4 (7)C14C—C13C—N1C—C4C91.4 (5)
C2B—C3B—N2B—O4B−177.8 (4)C18C—C13C—N1C—C1C84.0 (4)
C4B—C3B—N2B—O5B−174.2 (4)C14C—C13C—N1C—C1C−94.9 (4)
C2B—C3B—N2B—O5B3.6 (6)O2C—C1C—N1C—C4C119.2 (3)
N1A—C4A—S1—C5A26.9 (3)C8C—C1C—N1C—C4C−119.1 (3)
C3A—C4A—S1—C5A−150.5 (3)C2C—C1C—N1C—C4C−7.5 (3)
N1B—C4B—S2—C5B−6 (4)O2C—C1C—N1C—C13C−55.5 (4)
C3B—C4B—S2—C5B173 (4)C8C—C1C—N1C—C13C66.2 (4)
N1B—C4B—S2—C221.0 (5)C2C—C1C—N1C—C13C177.7 (3)
C3B—C4B—S2—C2−160.3 (5)C4C—C3C—N2C—O5C169.8 (4)
O2D—C1D—C2D—O3D−5.4 (4)C2C—C3C—N2C—O5C−4.7 (6)
N1D—C1D—C2D—O3D116.7 (3)C4C—C3C—N2C—O4C−9.1 (7)
C8D—C1D—C2D—O3D−126.2 (3)C2C—C3C—N2C—O4C176.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3B—H3B···O5B0.822.192.748 (4)125
O3C—H3C···O5C0.822.172.728 (4)126
O2A—H2A···O3Ai0.821.972.785 (3)175
O3A—H3A···O3Bii0.822.042.854 (3)172
O2B—H2B···O1Aiii0.822.012.787 (3)157
O2C—H2C···O5Div0.822.573.133 (4)127
O2C—H2C···O1Div0.822.032.797 (4)155
O3D—H3D···O3Civ0.822.042.857 (3)175
C10A—H10A···O5Aiii0.932.543.347 (5)146
C10C—H10C···O5Cv0.932.503.331 (6)149
C10D—H10D···O5Dv0.932.593.437 (5)151
C10B—H10B···O5Bii0.932.533.316 (6)142
C2—H20···O1Cvi0.962.503.446 (7)170
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, −y+2, −z+2; (v) x, y−1, z; (vi) −x, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3B—H3B···O5B0.822.192.748 (4)125.2
O3C—H3C···O5C0.822.172.728 (4)125.8
O2A—H2A···O3Ai0.821.972.785 (3)175.1
O3A—H3A···O3Bii0.822.042.854 (3)171.9
O2B—H2B···O1Aiii0.822.012.787 (3)156.9
O2C—H2C···O5Div0.822.573.133 (4)126.8
O2C—H2C···O1Div0.822.032.797 (4)154.9
O3D—H3D···O3Civ0.822.042.857 (3)175.1
C10A—H10A···O5Aiii0.932.543.347 (5)145.5
C10C—H10C···O5Cv0.932.503.331 (6)149.4
C10D—H10D···O5Dv0.932.593.437 (5)151.2
C10B—H10B···O5Bii0.932.533.316 (6)142.3
C2—H20···O1Cvi0.962.503.446 (7)170.2
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, −y+2, −z+2; (v) x, y−1, z; (vi) −x, −y+2, −z+1.
 

Acknowledgements

JS and RAN thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009).

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ISSN: 2056-9890
Volume 70| Part 3| March 2014| Pages o279-o280
doi:10.1107/S1600536814002712
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