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

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ISSN: 2056-9890

4-[(3-Benzamido­methyl-6-phenyl-6,7-di­hydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-7-yl)carbon­yl]-3-phenyl-1,2,3-oxa­diazol-3-ium-5-olate 0.06-hydrate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 16 November 2010; accepted 30 November 2010; online 15 December 2010)

The asymmetric unit of the title compound, C27H21N7O4S·0.06H2O, contains four syndone mol­ecules and a water mol­ecule with a site occupancy of 0.25. In two of the syndone mol­ecules, three atoms in a terminal phenyl ring are disordered over two sets of sites, with occupancy ratios of 0.500 (18):0.500 (18) and 0.512 (17):0.488 (17). The dihedral angles between terminal phenyl rings for the syndone mol­ecules are 23.3 (4), 45.57 (16), 68.46 (16) and 56.5 (3)°. In the crystal, mol­ecules are connected via N—H⋯N, N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For biological applications of sydnones, see: Newton & Ramsden (1982[Newton, C. G. & Ramsden, C. A. (1982). Tetrahedron, 38, 2965-3011.]); Wagner & Hill (1974[Wagner, H. & Hill, J. B. (1974). J. Med. Chem. 17, 1337-1338.]); Kalluraya & Rahiman (1997[Kalluraya, B. & Rahiman, A. M. (1997). Pol. J. Chem. 71, 1049-1052.]); Kalluraya et al. (2002[Kalluraya, B., Rahiman, A. & David, B. (2002). Indian J. Chem. Sect. B, 41, 1712-1717.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C27H21N7O4S·0.06H2O

  • Mr = 540.69

  • Triclinic, [P \overline 1]

  • a = 15.6242 (19) Å

  • b = 18.7430 (19) Å

  • c = 18.9689 (19) Å

  • α = 111.235 (2)°

  • β = 93.970 (2)°

  • γ = 101.636 (2)°

  • V = 5009.4 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 100 K

  • 0.64 × 0.08 × 0.07 mm

Data collection
  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.893, Tmax = 0.988

  • 54193 measured reflections

  • 17604 independent reflections

  • 12624 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.141

  • S = 1.04

  • 17604 reflections

  • 1498 parameters

  • 54 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.41 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H2W1⋯O2C 0.85 1.92 2.772 (4) 175
O1W—H1W1⋯N6B 0.85 2.10 2.944 (4) 174
N7A—H1NA⋯N5Bi 0.94 (5) 2.15 (5) 3.017 (4) 153 (4)
N7A—H1NA⋯N6Bi 0.94 (5) 2.19 (6) 3.016 (4) 146 (3)
N2A—H2NA⋯O3A 0.78 (3) 2.35 (3) 2.912 (3) 130 (3)
N7B—H1NB⋯N6Aii 0.86 (4) 2.16 (4) 2.964 (4) 155 (3)
N3B—H2NB⋯O3B 0.88 (3) 2.25 (3) 2.865 (3) 127 (3)
N7C—H1NC⋯N6Diii 0.80 (3) 2.21 (3) 2.990 (4) 165 (3)
N3C—H2NC⋯O3C 0.91 (3) 2.21 (3) 2.895 (3) 132 (3)
N7D—H1ND⋯N6Ciii 0.89 (3) 2.25 (3) 3.082 (4) 157 (3)
N3D—H2ND⋯O3D 0.94 (3) 2.07 (3) 2.841 (3) 138 (3)
C1A—H1XA⋯O2Bi 1.16 2.43 3.471 (10) 148
C5A—H5AA⋯O4Aiv 0.93 2.45 3.294 (4) 151
C1B—H1BA⋯O4Bv 0.93 2.40 3.278 (4) 158
C11A—H11A⋯O4Aiv 0.98 2.60 3.291 (4) 128
C5B—H5BA⋯O2Aii 0.93 2.51 3.405 (4) 162
C19D—H19D⋯O2Bvi 0.93 2.41 3.289 (11) 157
C5D—H5DA⋯O4Diii 0.93 2.47 3.328 (4) 154
C23A—H23A⋯O3Aiv 0.93 2.59 3.318 (4) 136
C23B—H23B⋯O3Bv 0.93 2.41 3.240 (4) 149
C27C—H27C⋯O3Cvii 0.93 2.52 3.359 (4) 150
C27D—H27D⋯O3Diii 0.93 2.42 3.258 (4) 149
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) -x+1, -y+1, -z; (iv) -x+2, -y, -z+1; (v) -x, -y+1, -z+1; (vi) x, y, z-1; (vii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Sydnones are class of mesoionic compounds containing a 1,2,3-oxadiazole ring system. A number of sydnone derivatives have shown diverse biological activities such as anti-inflammatory, analgesic and anti-arthritic (Newton & Ramsden, 1982; Wagner & Hill, 1974) properties. Sydnones possessing heterocyclic moieties at the 4-position are also known for a wide range of biological properties (Kalluraya & Rahiman, 1997). Encouraged by these reports and in continuation of our research for biologically active nitrogen containing heterocycles, a triazolothiadiazole moiety at the 4-position of the phenylsydnone was introduced. A series of triazolothiadiazoles were synthesized by the reaction of 2,3-dibromo-1-(3'-arylsydnon-4'-yl)-3-aryl- propan-1-one with 3-substituted-4-amino-5-mercapto-1,2,4-triazoles (Kalluraya et al., 2002).

The asymmetric unit of the title compound consists of two crystallographically independent syndone molecules (B & C) (Fig. 1a), two crystallographically independent disordered syndone molecules (A & D) (Fig. 1b) and a water molecule with a refined site occupancy of 0.25. In the disordered syndone molecules, three atoms C1A, C2A, C3A (molecule A) and C19D, C20D, C21D (molecule D) in the terminal phenyl rings are disordered over two positions, with occupancy ratios of 0.500 (18):0.500 (18) (molecule A) and 0.512 (17): 0.488 (17) (molecule D). The dihedral angles between terminal phenyl rings (C1A–C6A)/(C16A–C21A), (C1B–C6B)/(C16B–C21B), (C1C–C6C)/(C16C–C21C) and (C1D–C6D)/ (C16D–C21D) for all the syndone molecules are 23.3 (4)°, 45.57 (16)°, 68.46 (16)° and 56.5 (3)° respectively.

In the crystal structure (Fig. 2), all molecules are connected via intra and inter molecular N—H···N, N—H···O and C—H···O (Table 1) hydrogen bonds to form a three-dimensional network.

Related literature top

For biological applications of sydnones, see: Newton & Ramsden (1982); Wagner & Hill (1974); Kalluraya & Rahiman (1997); Kalluraya et al. (2002). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

N-[(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)methyl]benzamide (0.01 mol) and 2,3-dibromo-1-(3'-phenylsydnon-4'-yl)-3-phenyl-propan-1-one (0.01 mol) in ethanol was treated with aqueous solution of sodium acetate (0.01 mol). The reaction mixture was refluxed on a water bath for 1–2 hours. The excess of ethanol was removed by distillation and the reaction mixture was kept overnight. The solid product separated was filtered. It was then recrystallized from ethanol. Colourless needles were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.

Refinement top

Atoms H1NA, H2NA, H1NB, H2NB, H1NC, H2NC, H1ND and H2ND were located from a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically [N–H =0.78 (3)–0.89 (3)Å and C–H = 0.93–0.98 Å] and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C, O). In the final refinement, the occupancies of the water molecules were fixed at 25%. The C atoms C1A, C2A, C3A (molecule A) and C19D, C20D, C21D (molecule D) of the terminal phenyl ring and the associated hydrogen atoms are disordered over two sites with a refined occupancy ratio of 0.500 (18): 0.500 (18) (molecule A) and 0.512 (17): 0.488 (17) (molecule D) respectively.

Structure description top

Sydnones are class of mesoionic compounds containing a 1,2,3-oxadiazole ring system. A number of sydnone derivatives have shown diverse biological activities such as anti-inflammatory, analgesic and anti-arthritic (Newton & Ramsden, 1982; Wagner & Hill, 1974) properties. Sydnones possessing heterocyclic moieties at the 4-position are also known for a wide range of biological properties (Kalluraya & Rahiman, 1997). Encouraged by these reports and in continuation of our research for biologically active nitrogen containing heterocycles, a triazolothiadiazole moiety at the 4-position of the phenylsydnone was introduced. A series of triazolothiadiazoles were synthesized by the reaction of 2,3-dibromo-1-(3'-arylsydnon-4'-yl)-3-aryl- propan-1-one with 3-substituted-4-amino-5-mercapto-1,2,4-triazoles (Kalluraya et al., 2002).

The asymmetric unit of the title compound consists of two crystallographically independent syndone molecules (B & C) (Fig. 1a), two crystallographically independent disordered syndone molecules (A & D) (Fig. 1b) and a water molecule with a refined site occupancy of 0.25. In the disordered syndone molecules, three atoms C1A, C2A, C3A (molecule A) and C19D, C20D, C21D (molecule D) in the terminal phenyl rings are disordered over two positions, with occupancy ratios of 0.500 (18):0.500 (18) (molecule A) and 0.512 (17): 0.488 (17) (molecule D). The dihedral angles between terminal phenyl rings (C1A–C6A)/(C16A–C21A), (C1B–C6B)/(C16B–C21B), (C1C–C6C)/(C16C–C21C) and (C1D–C6D)/ (C16D–C21D) for all the syndone molecules are 23.3 (4)°, 45.57 (16)°, 68.46 (16)° and 56.5 (3)° respectively.

In the crystal structure (Fig. 2), all molecules are connected via intra and inter molecular N—H···N, N—H···O and C—H···O (Table 1) hydrogen bonds to form a three-dimensional network.

For biological applications of sydnones, see: Newton & Ramsden (1982); Wagner & Hill (1974); Kalluraya & Rahiman (1997); Kalluraya et al. (2002). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

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

Figures top
[Figure 1] Fig. 1. a. The undisordered syndone molecules in the title compound, showing 30% probability displacement ellipsoids [H atoms are omitted for clarity].
[Figure 2] Fig. 2. b. The disordered syndone molecules in the title compound, showing 30% probability displacement ellipsoids [H atoms are omitted for clarity]. Dotted lines represents disordered components.
[Figure 3] Fig. 3. The crystal packing of the title compound (I).
4-[(3-Benzamidomethyl-6-phenyl-6,7-dihydro-5H-1,2,4- triazolo[3,4-b][1,3,4]thiadiazin-7-yl)carbonyl]-3-phenyl- 1,2,3-oxadiazol-3-ium-5-olate 0.06-hydrate top
Crystal data top
C27H21N7O4S·0.06H2OZ = 8
Mr = 540.69F(000) = 2245
Triclinic, P1Dx = 1.434 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 15.6242 (19) ÅCell parameters from 8028 reflections
b = 18.7430 (19) Åθ = 2.7–26.3°
c = 18.9689 (19) ŵ = 0.18 mm1
α = 111.235 (2)°T = 100 K
β = 93.970 (2)°Needle, colourless
γ = 101.636 (2)°0.64 × 0.08 × 0.07 mm
V = 5009.4 (9) Å3
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
17604 independent reflections
Radiation source: fine-focus sealed tube12624 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1818
Tmin = 0.893, Tmax = 0.988k = 2222
54193 measured reflectionsl = 2222
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0647P)2 + 2.7459P]
where P = (Fo2 + 2Fc2)/3
17604 reflections(Δ/σ)max = 0.001
1498 parametersΔρmax = 1.41 e Å3
54 restraintsΔρmin = 0.30 e Å3
Crystal data top
C27H21N7O4S·0.06H2Oγ = 101.636 (2)°
Mr = 540.69V = 5009.4 (9) Å3
Triclinic, P1Z = 8
a = 15.6242 (19) ÅMo Kα radiation
b = 18.7430 (19) ŵ = 0.18 mm1
c = 18.9689 (19) ÅT = 100 K
α = 111.235 (2)°0.64 × 0.08 × 0.07 mm
β = 93.970 (2)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
17604 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
12624 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.988Rint = 0.057
54193 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04654 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 1.41 e Å3
17604 reflectionsΔρmin = 0.30 e Å3
1498 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
S1A0.81870 (4)0.17657 (4)0.48519 (4)0.02226 (16)
O1A0.63864 (15)0.14942 (12)0.67321 (12)0.0361 (5)
O2A0.64762 (13)0.12472 (12)0.54756 (12)0.0329 (5)
O3A0.92132 (14)0.14012 (12)0.63391 (11)0.0307 (5)
O4A1.21342 (14)0.03010 (12)0.41242 (12)0.0339 (5)
N1A0.76890 (18)0.15234 (14)0.71603 (13)0.0310 (6)
N2A0.98017 (16)0.09210 (14)0.48506 (15)0.0225 (5)
N3A0.6922 (2)0.15895 (15)0.73717 (15)0.0392 (7)
N4A0.97880 (14)0.14628 (13)0.44937 (12)0.0197 (5)
N5A0.93561 (15)0.22744 (14)0.40410 (13)0.0250 (5)
N6A1.01463 (15)0.21332 (14)0.37903 (14)0.0263 (5)
N7A1.17820 (16)0.14717 (16)0.45597 (17)0.0349 (6)
C1A0.8463 (8)0.2229 (5)0.8387 (5)0.035 (2)0.500 (18)
H1AA0.81640.26190.84220.042*0.500 (18)
C2A0.9055 (8)0.2260 (6)0.8986 (5)0.046 (3)0.500 (18)
H2AA0.91990.27090.94360.055*0.500 (18)
C3A0.9429 (9)0.1648 (11)0.8929 (9)0.048 (4)0.500 (18)
H3AA0.98360.17050.93400.058*0.500 (18)
C1X0.8951 (12)0.2263 (5)0.8283 (6)0.054 (4)0.500 (18)
H1XA0.89030.27470.82780.064*0.500 (18)
C2X0.9591 (11)0.2246 (6)0.8821 (6)0.058 (4)0.500 (18)
H2XA0.99250.27150.91990.069*0.500 (18)
C3X0.9725 (13)0.1545 (10)0.8794 (9)0.048 (4)0.500 (18)
H3XA1.01530.15200.91440.057*0.500 (18)
C4A0.9222 (2)0.0897 (2)0.8249 (2)0.0467 (9)
H4AA0.94760.04790.82120.056*
C5A0.8615 (2)0.0879 (2)0.76758 (18)0.0355 (7)
H5AA0.83770.04130.72530.043*
C6A0.8365 (2)0.15571 (19)0.77376 (17)0.0394 (8)
C7A0.6848 (2)0.13492 (16)0.60984 (18)0.0280 (7)
C8A0.7708 (2)0.13778 (16)0.64035 (16)0.0269 (6)
C9A0.84668 (19)0.12511 (16)0.60046 (16)0.0237 (6)
C10A0.82464 (18)0.09253 (16)0.51319 (15)0.0208 (6)
H10A0.76550.05680.49850.025*
C11A0.88942 (17)0.04434 (15)0.47488 (15)0.0207 (6)
H11A0.89370.00880.50150.025*
C12A0.91619 (17)0.18592 (15)0.44596 (15)0.0210 (6)
C13A1.03816 (17)0.16366 (16)0.40521 (16)0.0237 (6)
C14A1.11474 (18)0.12737 (18)0.38790 (18)0.0301 (7)
H14A1.09310.07050.36380.036*
H14B1.14440.14520.35180.036*
C15A1.22460 (17)0.09663 (16)0.46224 (17)0.0236 (6)
C16A1.29184 (18)0.12498 (16)0.53308 (17)0.0256 (6)
C17A1.2885 (2)0.18610 (17)0.60068 (18)0.0299 (7)
H17A1.24350.21230.60340.036*
C18A1.3522 (2)0.20800 (18)0.66406 (19)0.0343 (7)
H18A1.34960.24850.70950.041*
C19A1.4199 (2)0.16944 (19)0.65979 (19)0.0353 (7)
H19A1.46300.18450.70230.042*
C20A1.4236 (2)0.10878 (18)0.59263 (18)0.0327 (7)
H20A1.46950.08350.58970.039*
C21A1.35912 (18)0.08568 (17)0.52995 (17)0.0268 (6)
H21A1.36060.04360.48530.032*
C22A0.85938 (18)0.00858 (16)0.39070 (16)0.0220 (6)
C23A0.91430 (19)0.05525 (16)0.35411 (17)0.0267 (6)
H23A0.96850.05140.38060.032*
C24A0.8892 (2)0.10747 (18)0.27856 (18)0.0337 (7)
H24A0.92620.13880.25470.040*
C25A0.8090 (2)0.11292 (18)0.23861 (18)0.0348 (7)
H25A0.79160.14830.18800.042*
C26A0.7551 (2)0.06588 (17)0.27391 (17)0.0309 (7)
H26A0.70160.06890.24680.037*
C27A0.77978 (18)0.01383 (17)0.34973 (16)0.0258 (6)
H27A0.74280.01770.37320.031*
S1B0.02213 (5)0.33764 (4)0.63624 (4)0.02532 (17)
O1B0.24522 (14)0.32349 (12)0.73433 (12)0.0325 (5)
O2B0.09434 (15)0.36214 (13)0.75883 (12)0.0374 (5)
O3B0.14885 (12)0.37946 (12)0.53670 (11)0.0285 (5)
O4B0.13564 (14)0.45708 (11)0.31579 (12)0.0340 (5)
N1B0.27213 (15)0.34360 (13)0.63281 (13)0.0253 (5)
N2B0.31183 (17)0.32007 (14)0.68140 (15)0.0323 (6)
N3B0.03196 (16)0.42385 (14)0.51785 (13)0.0219 (5)
N4B0.08836 (14)0.37506 (13)0.52056 (12)0.0206 (5)
N5B0.16085 (16)0.30654 (14)0.56221 (14)0.0298 (6)
N6B0.20166 (16)0.32278 (15)0.50383 (14)0.0316 (6)
N7B0.10437 (16)0.35620 (15)0.35535 (13)0.0251 (5)
C1B0.3217 (2)0.42780 (17)0.57623 (17)0.0290 (7)
H1BA0.27840.47040.61070.035*
C2B0.3811 (2)0.43785 (18)0.52553 (18)0.0332 (7)
H2BA0.37800.48790.52540.040*
C3B0.4453 (2)0.3741 (2)0.4750 (2)0.0406 (8)
H3BA0.48590.38160.44170.049*
C4B0.4493 (2)0.2992 (2)0.4735 (2)0.0490 (9)
H4BA0.49140.25620.43810.059*
C5B0.3909 (2)0.28803 (18)0.5246 (2)0.0406 (8)
H5BA0.39400.23820.52520.049*
C6B0.32852 (18)0.35245 (17)0.57401 (17)0.0270 (6)
C7B0.1614 (2)0.35327 (17)0.71769 (17)0.0288 (7)
C8B0.18205 (18)0.36415 (16)0.64914 (16)0.0238 (6)
C9B0.12279 (18)0.38757 (16)0.60165 (16)0.0230 (6)
C10B0.02561 (18)0.42104 (16)0.63779 (16)0.0222 (6)
H10B0.02310.45530.69140.027*
C11B0.02394 (18)0.47146 (16)0.59823 (15)0.0217 (6)
H11B0.01190.50790.59550.026*
C12B0.09345 (18)0.33827 (15)0.57003 (15)0.0223 (6)
C13B0.15782 (18)0.36470 (17)0.48147 (16)0.0257 (6)
C14B0.17561 (19)0.39461 (18)0.42032 (16)0.0301 (7)
H14C0.18140.45120.44030.036*
H14D0.23090.38480.40370.036*
C15B0.08921 (19)0.39222 (16)0.30756 (16)0.0259 (6)
C16B0.01206 (19)0.35136 (16)0.24481 (16)0.0253 (6)
C17B0.0610 (2)0.29786 (17)0.24864 (17)0.0295 (7)
H17B0.06190.28310.29050.035*
C18B0.1326 (2)0.26633 (19)0.19035 (19)0.0397 (8)
H18B0.18190.23080.19320.048*
C19B0.1306 (3)0.2876 (2)0.1282 (2)0.0487 (9)
H19B0.17880.26600.08900.058*
C20B0.0585 (3)0.3401 (2)0.1232 (2)0.0514 (10)
H20B0.05770.35370.08070.062*
C21B0.0128 (2)0.3726 (2)0.18164 (19)0.0395 (8)
H21B0.06140.40880.17880.047*
C22B0.11491 (18)0.52202 (15)0.64050 (16)0.0220 (6)
C23B0.16575 (19)0.56588 (17)0.60627 (17)0.0287 (7)
H23B0.14330.56360.55860.034*
C24B0.2489 (2)0.61289 (18)0.64159 (18)0.0336 (7)
H24B0.28220.64180.61770.040*
C25B0.2827 (2)0.61692 (18)0.71262 (19)0.0351 (7)
H25B0.33860.64880.73680.042*
C26B0.2334 (2)0.57374 (18)0.74723 (19)0.0348 (7)
H26B0.25600.57640.79500.042*
C27B0.15042 (19)0.52630 (16)0.71131 (16)0.0275 (7)
H27B0.11790.49680.73500.033*
S1C0.48300 (5)0.26223 (4)0.15697 (4)0.02559 (17)
O1C0.19815 (15)0.16423 (15)0.22509 (14)0.0466 (6)
O2C0.34340 (16)0.22827 (14)0.26351 (13)0.0414 (6)
O3C0.34333 (12)0.08877 (12)0.02058 (12)0.0299 (5)
O4C0.69901 (14)0.00973 (13)0.13738 (13)0.0399 (6)
N1C0.19460 (16)0.10302 (15)0.10598 (16)0.0328 (6)
N2C0.14369 (18)0.11339 (19)0.15804 (18)0.0462 (7)
N3C0.53334 (16)0.11028 (13)0.03307 (14)0.0228 (5)
N4C0.57434 (14)0.18924 (13)0.04532 (13)0.0207 (5)
N5C0.59980 (17)0.31759 (14)0.07845 (14)0.0304 (6)
N6C0.65470 (16)0.28738 (15)0.02506 (14)0.0304 (6)
N7C0.62830 (16)0.10687 (15)0.11771 (14)0.0262 (6)
C1C0.1262 (2)0.0297 (2)0.0143 (2)0.0429 (9)
H1CA0.13490.04850.05280.051*
C2C0.0858 (2)0.0807 (2)0.0585 (2)0.0478 (9)
H2CA0.06620.13430.06920.057*
C3C0.0743 (2)0.0528 (2)0.1155 (2)0.0487 (9)
H3CA0.04730.08750.16460.058*
C4C0.1029 (2)0.0270 (3)0.0995 (2)0.0519 (10)
H4CA0.09560.04570.13820.062*
C5C0.1423 (2)0.0793 (2)0.0264 (2)0.0448 (9)
H5CA0.16080.13320.01500.054*
C6C0.15331 (19)0.04922 (19)0.02876 (19)0.0338 (7)
C7C0.2858 (2)0.18375 (19)0.2114 (2)0.0349 (8)
C8C0.28101 (19)0.14226 (17)0.13221 (18)0.0286 (7)
C9C0.35350 (18)0.12604 (16)0.08981 (18)0.0256 (6)
C10C0.44429 (18)0.15702 (16)0.13905 (16)0.0239 (6)
H10C0.43620.15360.18860.029*
C11C0.50822 (17)0.10585 (16)0.10525 (15)0.0214 (6)
H11C0.47460.05130.09130.026*
C12C0.55301 (18)0.25668 (16)0.08875 (16)0.0239 (6)
C13C0.63826 (18)0.21076 (17)0.00678 (15)0.0255 (6)
C14C0.68399 (19)0.15572 (18)0.04461 (16)0.0295 (7)
H14E0.73770.18570.05320.035*
H14F0.70070.12210.02010.035*
C15C0.64339 (18)0.03716 (17)0.16049 (17)0.0258 (6)
C16C0.58866 (18)0.00515 (16)0.23813 (16)0.0245 (6)
C17C0.5075 (2)0.00949 (17)0.25619 (18)0.0312 (7)
H17C0.48380.04470.21910.037*
C18C0.4630 (2)0.02942 (19)0.33027 (19)0.0389 (8)
H18C0.40880.02050.34320.047*
C19C0.4982 (2)0.08132 (19)0.38510 (19)0.0417 (9)
H19C0.46820.10600.43510.050*
C20C0.5774 (2)0.09711 (19)0.36676 (19)0.0402 (8)
H20C0.60030.13310.40380.048*
C21C0.6220 (2)0.05916 (17)0.29329 (17)0.0320 (7)
H21C0.67520.06990.28040.038*
C22C0.58901 (18)0.11634 (16)0.16028 (16)0.0242 (6)
C23C0.6062 (2)0.16828 (17)0.23681 (18)0.0322 (7)
H23C0.56920.20160.25560.039*
C24C0.6789 (2)0.17039 (19)0.2853 (2)0.0406 (8)
H24C0.69020.20520.33630.049*
C25C0.7340 (2)0.1210 (2)0.2579 (2)0.0427 (9)
H25C0.78240.12250.29040.051*
C26C0.7171 (2)0.0696 (2)0.1825 (2)0.0388 (8)
H26C0.75390.03590.16400.047*
C27C0.64560 (19)0.06778 (18)0.13399 (19)0.0309 (7)
H27C0.63540.03340.08290.037*
S1D0.67540 (5)0.74950 (4)0.01406 (4)0.02542 (17)
O1D0.77315 (16)0.67127 (13)0.22023 (13)0.0414 (6)
O2D0.81168 (15)0.71952 (13)0.09094 (14)0.0377 (5)
O3D0.54384 (14)0.56927 (13)0.12470 (11)0.0338 (5)
O4D0.30364 (16)0.53490 (12)0.13597 (12)0.0395 (5)
N1D0.64817 (17)0.59195 (14)0.23674 (14)0.0303 (6)
N2D0.7045 (2)0.61867 (17)0.27436 (16)0.0407 (7)
N3D0.52802 (16)0.61112 (13)0.03269 (14)0.0252 (5)
N4D0.53310 (15)0.69244 (13)0.07243 (12)0.0222 (5)
N5D0.56679 (15)0.82093 (14)0.10592 (14)0.0284 (6)
N6D0.49628 (15)0.79944 (15)0.14236 (14)0.0301 (6)
N7D0.33468 (15)0.62925 (14)0.08854 (14)0.0259 (5)
C1D0.5087 (3)0.5518 (2)0.32158 (18)0.0445 (9)
H1DA0.51570.60330.31870.053*
C2D0.4363 (3)0.4928 (3)0.3663 (2)0.0539 (11)
H2DA0.39320.50490.39330.065*
C3D0.4268 (2)0.4159 (2)0.37144 (19)0.0448 (9)
H3DA0.37810.37660.40240.054*
C4D0.4899 (2)0.3975 (2)0.33049 (18)0.0375 (8)
H4DA0.48380.34580.33420.045*
C5D0.5613 (2)0.45567 (18)0.28440 (17)0.0317 (7)
H5DA0.60330.44430.25560.038*
C6D0.5697 (2)0.53196 (18)0.28169 (16)0.0316 (7)
C7D0.7583 (2)0.67542 (19)0.14649 (19)0.0313 (7)
C8D0.6751 (2)0.62235 (17)0.16016 (16)0.0274 (7)
C9D0.6211 (2)0.60676 (17)0.10561 (17)0.0272 (7)
C10D0.66614 (19)0.64259 (16)0.02236 (15)0.0243 (6)
H10D0.72630.63480.02190.029*
C11D0.61791 (19)0.59872 (16)0.02358 (16)0.0243 (6)
H11D0.60940.54240.00740.029*
C12D0.58650 (18)0.75537 (16)0.06481 (16)0.0232 (6)
C13D0.47891 (18)0.72224 (17)0.12128 (16)0.0261 (6)
C14D0.41083 (19)0.6744 (2)0.14785 (17)0.0326 (7)
H14G0.43680.63850.16340.039*
H14H0.39150.70920.19220.039*
C15D0.2857 (2)0.56152 (17)0.08784 (16)0.0273 (6)
C16D0.2073 (2)0.52059 (17)0.02742 (17)0.0298 (7)
C17D0.1970 (2)0.53132 (18)0.04070 (17)0.0309 (7)
H17D0.24060.56730.04990.037*
C18D0.1229 (2)0.4895 (2)0.09543 (19)0.0451 (9)
H18D0.12550.48710.14500.054*
C19D0.0480 (8)0.4523 (7)0.0815 (6)0.043 (2)0.512 (17)
H19D0.00350.43190.11720.051*0.512 (17)
C20D0.0509 (7)0.4456 (6)0.0113 (5)0.048 (3)0.512 (17)
H20D0.00100.41850.00050.058*0.512 (17)
C21D0.1282 (8)0.4792 (7)0.0418 (5)0.040 (3)0.512 (17)
H21D0.12810.47430.08890.048*0.512 (17)
C19X0.0692 (7)0.4219 (9)0.0848 (6)0.044 (3)0.488 (17)
H19E0.02230.38830.12270.053*0.488 (17)
C20X0.0857 (6)0.4063 (7)0.0207 (5)0.041 (3)0.488 (17)
H20E0.04840.36390.01500.050*0.488 (17)
C21X0.1575 (7)0.4531 (6)0.0360 (5)0.031 (2)0.488 (17)
H21E0.17200.44060.07780.037*0.488 (17)
C22D0.6686 (2)0.61265 (16)0.10021 (16)0.0270 (6)
C23D0.7508 (2)0.66351 (18)0.13177 (18)0.0368 (8)
H23D0.77770.69410.10650.044*
C24D0.7940 (3)0.6694 (2)0.20131 (19)0.0455 (9)
H24D0.84930.70390.22240.055*
C25D0.7542 (3)0.6238 (2)0.23845 (18)0.0434 (9)
H25D0.78290.62750.28470.052*
C26D0.6728 (2)0.5730 (2)0.20766 (18)0.0396 (8)
H26D0.64650.54190.23270.048*
C27D0.6299 (2)0.56810 (18)0.13995 (17)0.0318 (7)
H27D0.57390.53440.12010.038*
H1NA1.193 (3)0.200 (3)0.490 (2)0.065 (12)*
H2NA0.998 (2)0.1156 (18)0.5284 (18)0.023 (9)*
H1NB0.0761 (19)0.3090 (19)0.3471 (17)0.025 (8)*
H2NB0.018 (2)0.3892 (18)0.4936 (18)0.028 (9)*
H1NC0.595 (2)0.1273 (19)0.1330 (18)0.029 (9)*
H2NC0.482 (2)0.0965 (17)0.0007 (17)0.028 (8)*
H1ND0.3206 (19)0.6484 (17)0.0539 (17)0.027 (8)*
H2ND0.502 (2)0.593 (2)0.019 (2)0.046 (10)*
O1W0.3466 (6)0.2769 (5)0.4204 (5)0.042 (2)*0.25
H1W10.30210.28780.44180.064*0.25
H2W10.34860.26310.37270.064*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0232 (4)0.0242 (4)0.0232 (4)0.0071 (3)0.0038 (3)0.0127 (3)
O1A0.0481 (13)0.0325 (12)0.0348 (13)0.0153 (10)0.0233 (11)0.0151 (10)
O2A0.0354 (12)0.0379 (12)0.0329 (13)0.0173 (10)0.0087 (10)0.0171 (10)
O3A0.0362 (12)0.0353 (12)0.0205 (11)0.0102 (10)0.0004 (9)0.0107 (9)
O4A0.0463 (13)0.0289 (12)0.0271 (12)0.0157 (10)0.0048 (10)0.0081 (10)
N1A0.0559 (17)0.0210 (13)0.0194 (13)0.0106 (12)0.0119 (12)0.0097 (11)
N2A0.0248 (13)0.0236 (13)0.0206 (14)0.0049 (10)0.0016 (11)0.0117 (12)
N3A0.0622 (19)0.0297 (14)0.0314 (16)0.0118 (14)0.0225 (15)0.0152 (13)
N4A0.0206 (12)0.0213 (12)0.0179 (12)0.0024 (9)0.0003 (9)0.0103 (10)
N5A0.0223 (12)0.0290 (13)0.0265 (13)0.0028 (10)0.0023 (10)0.0160 (11)
N6A0.0218 (12)0.0291 (13)0.0308 (14)0.0046 (10)0.0037 (10)0.0158 (11)
N7A0.0271 (14)0.0231 (14)0.0468 (17)0.0044 (11)0.0104 (12)0.0085 (13)
C1A0.034 (5)0.045 (4)0.019 (4)0.007 (4)0.004 (4)0.015 (3)
C2A0.044 (6)0.055 (5)0.025 (4)0.015 (4)0.001 (4)0.016 (4)
C3A0.037 (7)0.079 (10)0.020 (6)0.011 (6)0.002 (4)0.025 (6)
C1X0.085 (9)0.025 (4)0.043 (5)0.012 (5)0.019 (6)0.010 (4)
C2X0.083 (10)0.042 (5)0.034 (5)0.014 (5)0.025 (5)0.005 (4)
C3X0.081 (11)0.048 (5)0.027 (6)0.033 (7)0.012 (6)0.018 (4)
C4A0.046 (2)0.062 (2)0.038 (2)0.0108 (19)0.0044 (17)0.026 (2)
C5A0.0353 (18)0.0410 (19)0.0288 (18)0.0095 (15)0.0059 (14)0.0115 (15)
C6A0.069 (2)0.0311 (17)0.0152 (16)0.0019 (16)0.0015 (15)0.0113 (14)
C7A0.0390 (18)0.0211 (15)0.0300 (18)0.0115 (13)0.0179 (15)0.0125 (13)
C8A0.0425 (18)0.0233 (15)0.0196 (15)0.0131 (13)0.0080 (13)0.0105 (13)
C9A0.0349 (17)0.0204 (14)0.0195 (15)0.0095 (12)0.0044 (13)0.0105 (12)
C10A0.0231 (14)0.0222 (14)0.0190 (15)0.0037 (11)0.0008 (11)0.0114 (12)
C11A0.0242 (14)0.0215 (14)0.0200 (15)0.0063 (12)0.0036 (12)0.0118 (12)
C12A0.0196 (14)0.0209 (14)0.0207 (15)0.0012 (11)0.0036 (11)0.0092 (12)
C13A0.0204 (14)0.0253 (15)0.0250 (16)0.0004 (12)0.0010 (12)0.0125 (13)
C14A0.0224 (15)0.0356 (17)0.0346 (18)0.0053 (13)0.0029 (13)0.0175 (15)
C15A0.0208 (14)0.0228 (15)0.0325 (17)0.0035 (12)0.0106 (12)0.0164 (14)
C16A0.0237 (15)0.0236 (15)0.0339 (17)0.0030 (12)0.0070 (13)0.0170 (14)
C17A0.0317 (17)0.0239 (15)0.0370 (18)0.0107 (13)0.0083 (14)0.0126 (14)
C18A0.0382 (18)0.0288 (16)0.0336 (18)0.0092 (14)0.0052 (15)0.0090 (14)
C19A0.0321 (17)0.0381 (18)0.0341 (19)0.0048 (14)0.0015 (14)0.0151 (16)
C20A0.0279 (16)0.0368 (18)0.042 (2)0.0139 (14)0.0096 (14)0.0212 (16)
C21A0.0295 (16)0.0246 (15)0.0306 (17)0.0097 (13)0.0090 (13)0.0132 (13)
C22A0.0258 (15)0.0211 (14)0.0225 (15)0.0030 (12)0.0053 (12)0.0135 (12)
C23A0.0280 (16)0.0261 (15)0.0286 (17)0.0061 (13)0.0068 (13)0.0132 (14)
C24A0.0403 (19)0.0286 (16)0.0324 (18)0.0098 (14)0.0133 (15)0.0098 (14)
C25A0.049 (2)0.0259 (16)0.0210 (16)0.0005 (15)0.0052 (15)0.0043 (13)
C26A0.0360 (17)0.0285 (16)0.0245 (17)0.0042 (14)0.0007 (14)0.0088 (14)
C27A0.0266 (15)0.0269 (15)0.0240 (16)0.0045 (12)0.0040 (12)0.0110 (13)
S1B0.0342 (4)0.0249 (4)0.0228 (4)0.0088 (3)0.0059 (3)0.0148 (3)
O1B0.0407 (12)0.0306 (11)0.0305 (12)0.0062 (10)0.0145 (10)0.0165 (10)
O2B0.0431 (14)0.0463 (14)0.0266 (12)0.0044 (11)0.0050 (11)0.0218 (11)
O3B0.0283 (11)0.0378 (12)0.0261 (12)0.0095 (9)0.0083 (9)0.0186 (10)
O4B0.0404 (12)0.0198 (10)0.0436 (14)0.0049 (9)0.0132 (10)0.0142 (10)
N1B0.0321 (14)0.0201 (12)0.0280 (14)0.0078 (10)0.0154 (11)0.0116 (11)
N2B0.0369 (15)0.0277 (14)0.0377 (16)0.0072 (11)0.0145 (13)0.0177 (12)
N3B0.0232 (13)0.0270 (13)0.0196 (13)0.0102 (11)0.0043 (10)0.0113 (11)
N4B0.0216 (12)0.0234 (12)0.0163 (12)0.0067 (10)0.0020 (10)0.0066 (10)
N5B0.0354 (14)0.0285 (13)0.0236 (14)0.0139 (11)0.0007 (11)0.0055 (11)
N6B0.0324 (14)0.0346 (14)0.0218 (14)0.0123 (12)0.0032 (11)0.0022 (12)
N7B0.0312 (14)0.0211 (13)0.0197 (13)0.0010 (11)0.0062 (11)0.0078 (11)
C1B0.0339 (17)0.0249 (15)0.0314 (17)0.0074 (13)0.0160 (14)0.0126 (14)
C2B0.0417 (19)0.0280 (16)0.0380 (19)0.0128 (15)0.0171 (15)0.0177 (15)
C3B0.0360 (19)0.044 (2)0.051 (2)0.0141 (16)0.0085 (16)0.0250 (18)
C4B0.041 (2)0.0337 (19)0.065 (3)0.0020 (16)0.0092 (18)0.0177 (19)
C5B0.0408 (19)0.0210 (16)0.057 (2)0.0048 (14)0.0005 (17)0.0149 (16)
C6B0.0258 (15)0.0257 (15)0.0327 (17)0.0095 (13)0.0122 (13)0.0119 (14)
C7B0.0408 (19)0.0226 (15)0.0263 (17)0.0081 (13)0.0170 (15)0.0111 (13)
C8B0.0295 (16)0.0193 (14)0.0230 (15)0.0052 (12)0.0090 (12)0.0082 (12)
C9B0.0296 (16)0.0204 (14)0.0221 (16)0.0097 (12)0.0096 (12)0.0088 (12)
C10B0.0285 (15)0.0212 (14)0.0189 (15)0.0070 (12)0.0053 (12)0.0092 (12)
C11B0.0263 (15)0.0247 (14)0.0213 (15)0.0108 (12)0.0092 (12)0.0139 (12)
C12B0.0312 (16)0.0178 (13)0.0140 (14)0.0049 (12)0.0014 (12)0.0031 (11)
C13B0.0223 (15)0.0303 (16)0.0191 (15)0.0051 (13)0.0024 (12)0.0043 (13)
C14B0.0266 (16)0.0344 (17)0.0227 (16)0.0001 (13)0.0050 (13)0.0072 (14)
C15B0.0346 (17)0.0223 (15)0.0235 (16)0.0104 (13)0.0173 (13)0.0078 (13)
C16B0.0366 (17)0.0222 (14)0.0217 (15)0.0137 (13)0.0112 (13)0.0089 (12)
C17B0.0415 (18)0.0238 (15)0.0240 (16)0.0093 (14)0.0023 (14)0.0098 (13)
C18B0.048 (2)0.0310 (17)0.0350 (19)0.0075 (15)0.0061 (16)0.0095 (15)
C19B0.059 (2)0.050 (2)0.031 (2)0.0192 (19)0.0102 (17)0.0089 (17)
C20B0.071 (3)0.071 (3)0.030 (2)0.037 (2)0.0141 (19)0.0289 (19)
C21B0.050 (2)0.048 (2)0.0355 (19)0.0218 (17)0.0181 (17)0.0265 (17)
C22B0.0289 (15)0.0191 (14)0.0217 (15)0.0113 (12)0.0086 (12)0.0083 (12)
C23B0.0350 (17)0.0269 (15)0.0278 (17)0.0077 (13)0.0099 (14)0.0139 (14)
C24B0.0363 (18)0.0268 (16)0.0373 (19)0.0050 (14)0.0129 (15)0.0122 (15)
C25B0.0317 (17)0.0275 (16)0.0375 (19)0.0028 (14)0.0011 (14)0.0058 (15)
C26B0.0394 (19)0.0308 (17)0.0306 (18)0.0049 (14)0.0015 (14)0.0109 (15)
C27B0.0357 (17)0.0225 (15)0.0240 (16)0.0056 (13)0.0064 (13)0.0091 (13)
S1C0.0299 (4)0.0212 (4)0.0263 (4)0.0079 (3)0.0059 (3)0.0086 (3)
O1C0.0396 (14)0.0583 (16)0.0510 (16)0.0172 (12)0.0252 (12)0.0256 (13)
O2C0.0451 (14)0.0393 (13)0.0391 (14)0.0163 (12)0.0177 (12)0.0091 (12)
O3C0.0246 (11)0.0335 (12)0.0291 (13)0.0042 (9)0.0037 (9)0.0109 (10)
O4C0.0427 (13)0.0402 (13)0.0395 (13)0.0149 (11)0.0074 (11)0.0181 (11)
N1C0.0264 (14)0.0393 (15)0.0457 (17)0.0119 (12)0.0173 (13)0.0270 (14)
N2C0.0346 (16)0.062 (2)0.052 (2)0.0147 (15)0.0224 (15)0.0296 (17)
N3C0.0225 (13)0.0217 (12)0.0211 (13)0.0018 (10)0.0028 (11)0.0068 (10)
N4C0.0220 (12)0.0195 (12)0.0194 (12)0.0022 (10)0.0015 (10)0.0080 (10)
N5C0.0399 (15)0.0253 (13)0.0245 (14)0.0003 (11)0.0002 (12)0.0127 (11)
N6C0.0360 (14)0.0316 (14)0.0202 (13)0.0018 (11)0.0024 (11)0.0117 (11)
N7C0.0279 (14)0.0342 (15)0.0191 (13)0.0096 (12)0.0036 (11)0.0122 (12)
C1C0.040 (2)0.049 (2)0.053 (2)0.0169 (17)0.0129 (17)0.0319 (19)
C2C0.042 (2)0.049 (2)0.053 (2)0.0106 (17)0.0084 (18)0.020 (2)
C3C0.0249 (18)0.074 (3)0.047 (2)0.0086 (18)0.0055 (16)0.025 (2)
C4C0.0234 (18)0.087 (3)0.059 (3)0.0050 (19)0.0008 (17)0.049 (2)
C5C0.0239 (17)0.059 (2)0.064 (3)0.0033 (16)0.0026 (17)0.042 (2)
C6C0.0179 (15)0.0454 (19)0.047 (2)0.0082 (14)0.0102 (14)0.0268 (17)
C7C0.0368 (19)0.0317 (17)0.047 (2)0.0162 (15)0.0199 (17)0.0207 (17)
C8C0.0267 (16)0.0289 (16)0.0382 (19)0.0096 (13)0.0121 (14)0.0194 (15)
C9C0.0255 (15)0.0231 (15)0.0338 (19)0.0065 (12)0.0075 (13)0.0166 (14)
C10C0.0276 (15)0.0214 (14)0.0253 (16)0.0051 (12)0.0075 (12)0.0117 (13)
C11C0.0238 (14)0.0187 (14)0.0228 (15)0.0049 (11)0.0075 (12)0.0086 (12)
C12C0.0278 (15)0.0249 (15)0.0172 (15)0.0016 (12)0.0038 (12)0.0101 (12)
C13C0.0234 (15)0.0332 (17)0.0156 (15)0.0042 (12)0.0029 (12)0.0114 (13)
C14C0.0265 (16)0.0397 (18)0.0186 (15)0.0037 (13)0.0040 (12)0.0091 (14)
C15C0.0277 (16)0.0271 (15)0.0268 (16)0.0033 (13)0.0045 (13)0.0170 (14)
C16C0.0273 (15)0.0229 (14)0.0252 (16)0.0017 (12)0.0039 (12)0.0138 (13)
C17C0.0327 (17)0.0239 (15)0.0347 (18)0.0037 (13)0.0020 (14)0.0118 (14)
C18C0.0378 (19)0.0325 (18)0.041 (2)0.0010 (15)0.0139 (16)0.0155 (16)
C19C0.054 (2)0.0313 (18)0.0261 (18)0.0091 (16)0.0094 (16)0.0083 (15)
C20C0.049 (2)0.0311 (18)0.0320 (19)0.0014 (16)0.0083 (16)0.0082 (15)
C21C0.0352 (17)0.0288 (16)0.0310 (18)0.0033 (14)0.0069 (14)0.0124 (14)
C22C0.0241 (15)0.0224 (14)0.0281 (16)0.0029 (12)0.0056 (12)0.0132 (13)
C23C0.0422 (18)0.0231 (15)0.0326 (18)0.0098 (14)0.0008 (14)0.0126 (14)
C24C0.054 (2)0.0298 (17)0.0330 (19)0.0019 (16)0.0104 (16)0.0143 (15)
C25C0.0368 (19)0.042 (2)0.051 (2)0.0013 (16)0.0110 (17)0.0285 (19)
C26C0.0275 (17)0.0404 (19)0.056 (2)0.0128 (15)0.0066 (16)0.0254 (18)
C27C0.0272 (16)0.0325 (17)0.0349 (18)0.0066 (13)0.0050 (14)0.0156 (15)
S1D0.0302 (4)0.0243 (4)0.0256 (4)0.0069 (3)0.0088 (3)0.0131 (3)
O1D0.0602 (16)0.0350 (13)0.0376 (14)0.0171 (12)0.0295 (12)0.0172 (11)
O2D0.0384 (13)0.0338 (12)0.0449 (15)0.0114 (11)0.0188 (11)0.0160 (12)
O3D0.0349 (13)0.0419 (13)0.0197 (11)0.0028 (10)0.0059 (9)0.0094 (10)
O4D0.0606 (15)0.0336 (12)0.0302 (12)0.0125 (11)0.0001 (11)0.0197 (11)
N1D0.0503 (16)0.0297 (14)0.0236 (14)0.0234 (13)0.0186 (12)0.0154 (12)
N2D0.0631 (19)0.0424 (16)0.0319 (16)0.0243 (15)0.0277 (15)0.0222 (14)
N3D0.0313 (14)0.0221 (12)0.0176 (13)0.0004 (10)0.0039 (11)0.0055 (11)
N4D0.0271 (13)0.0218 (12)0.0154 (12)0.0030 (10)0.0028 (10)0.0061 (10)
N5D0.0266 (13)0.0283 (13)0.0283 (14)0.0061 (11)0.0038 (11)0.0090 (12)
N6D0.0253 (13)0.0332 (14)0.0274 (14)0.0066 (11)0.0047 (11)0.0069 (12)
N7D0.0260 (13)0.0305 (14)0.0227 (14)0.0025 (11)0.0018 (11)0.0149 (12)
C1D0.073 (3)0.049 (2)0.0204 (17)0.037 (2)0.0065 (17)0.0115 (16)
C2D0.069 (3)0.083 (3)0.0243 (19)0.050 (2)0.0074 (18)0.020 (2)
C3D0.046 (2)0.064 (2)0.0220 (17)0.0215 (19)0.0064 (15)0.0102 (17)
C4D0.0425 (19)0.047 (2)0.0269 (18)0.0125 (16)0.0141 (15)0.0164 (16)
C5D0.0411 (18)0.0405 (18)0.0242 (16)0.0179 (15)0.0128 (14)0.0192 (15)
C6D0.050 (2)0.0385 (18)0.0151 (15)0.0247 (16)0.0131 (14)0.0115 (14)
C7D0.0434 (19)0.0307 (17)0.0337 (19)0.0204 (15)0.0246 (16)0.0190 (15)
C8D0.0401 (18)0.0282 (16)0.0226 (16)0.0165 (14)0.0135 (13)0.0140 (13)
C9D0.0353 (18)0.0286 (16)0.0236 (16)0.0130 (14)0.0094 (13)0.0130 (13)
C10D0.0299 (16)0.0243 (15)0.0194 (15)0.0059 (12)0.0065 (12)0.0091 (12)
C11D0.0347 (16)0.0194 (14)0.0190 (15)0.0061 (12)0.0081 (12)0.0071 (12)
C12D0.0235 (15)0.0277 (15)0.0196 (15)0.0058 (12)0.0011 (12)0.0112 (13)
C13D0.0227 (15)0.0350 (17)0.0176 (15)0.0047 (13)0.0012 (12)0.0084 (13)
C14D0.0248 (16)0.0461 (19)0.0209 (16)0.0006 (14)0.0023 (13)0.0105 (14)
C15D0.0380 (17)0.0263 (15)0.0220 (16)0.0136 (13)0.0104 (13)0.0104 (13)
C16D0.0371 (17)0.0258 (15)0.0218 (16)0.0002 (13)0.0061 (13)0.0075 (13)
C17D0.0342 (17)0.0309 (16)0.0283 (17)0.0037 (14)0.0023 (14)0.0147 (14)
C18D0.047 (2)0.054 (2)0.0270 (19)0.0055 (18)0.0012 (16)0.0116 (17)
C19D0.042 (6)0.037 (6)0.040 (5)0.007 (4)0.000 (4)0.007 (4)
C20D0.035 (5)0.041 (6)0.050 (5)0.010 (4)0.005 (4)0.008 (4)
C21D0.052 (6)0.040 (6)0.025 (4)0.002 (5)0.011 (4)0.016 (4)
C19X0.029 (5)0.046 (7)0.039 (5)0.002 (4)0.008 (4)0.003 (5)
C20X0.031 (5)0.045 (6)0.043 (5)0.009 (4)0.003 (4)0.021 (4)
C21X0.029 (5)0.028 (5)0.034 (4)0.006 (3)0.005 (3)0.009 (4)
C22D0.0418 (18)0.0223 (15)0.0178 (15)0.0111 (13)0.0046 (13)0.0069 (12)
C23D0.050 (2)0.0271 (16)0.0321 (18)0.0056 (15)0.0063 (15)0.0144 (15)
C24D0.061 (2)0.0307 (18)0.033 (2)0.0085 (17)0.0130 (17)0.0042 (16)
C25D0.072 (3)0.044 (2)0.0209 (17)0.031 (2)0.0019 (17)0.0125 (16)
C26D0.061 (2)0.046 (2)0.0260 (18)0.0286 (19)0.0171 (17)0.0195 (16)
C27D0.0440 (19)0.0318 (17)0.0272 (17)0.0139 (14)0.0125 (14)0.0166 (14)
Geometric parameters (Å, º) top
S1A—C12A1.746 (3)S1C—C10C1.837 (3)
S1A—C10A1.852 (3)O1C—N2C1.376 (4)
O1A—N3A1.359 (3)O1C—C7C1.412 (4)
O1A—C7A1.415 (3)O2C—C7C1.208 (4)
O2A—C7A1.211 (4)O3C—C9C1.224 (3)
O3A—C9A1.216 (3)O4C—C15C1.226 (3)
O4A—C15A1.230 (3)N1C—N2C1.295 (4)
N1A—N3A1.305 (4)N1C—C8C1.361 (4)
N1A—C8A1.364 (4)N1C—C6C1.454 (4)
N1A—C6A1.443 (4)N3C—N4C1.415 (3)
N2A—N4A1.412 (3)N3C—C11C1.476 (3)
N2A—C11A1.474 (4)N3C—H2NC0.91 (3)
N2A—H2NA0.78 (3)N4C—C12C1.357 (4)
N4A—C12A1.354 (3)N4C—C13C1.359 (3)
N4A—C13A1.361 (3)N5C—C12C1.312 (4)
N5A—C12A1.309 (3)N5C—N6C1.408 (4)
N5A—N6A1.394 (3)N6C—C13C1.314 (4)
N6A—C13A1.302 (3)N7C—C15C1.343 (4)
N7A—C15A1.336 (4)N7C—C14C1.453 (4)
N7A—C14A1.454 (4)N7C—H1NC0.80 (3)
N7A—H1NA0.94 (4)C1C—C6C1.372 (5)
C1A—C6A1.378 (10)C1C—C2C1.378 (5)
C1A—C2A1.391 (12)C1C—H1CA0.9300
C1A—H1AA0.9300C2C—C3C1.377 (5)
C2A—C3A1.364 (19)C2C—H2CA0.9300
C2A—H2AA0.9300C3C—C4C1.382 (5)
C3A—C4A1.482 (19)C3C—H3CA0.9300
C3A—H3AA0.9300C4C—C5C1.384 (5)
C1X—C2X1.391 (12)C4C—H4CA0.9300
C1X—C6A1.431 (11)C5C—C6C1.372 (4)
C1X—H1XA0.9300C5C—H5CA0.9300
C2X—C3X1.356 (19)C7C—C8C1.408 (5)
C2X—H2XA0.9300C8C—C9C1.453 (4)
C3X—C4A1.325 (18)C9C—C10C1.521 (4)
C3X—H3XA0.9300C10C—C11C1.535 (4)
C4A—C5A1.379 (5)C10C—H10C0.9800
C4A—H4AA0.9300C11C—C22C1.514 (4)
C5A—C6A1.371 (5)C11C—H11C0.9800
C5A—H5AA0.9300C13C—C14C1.480 (4)
C7A—C8A1.409 (4)C14C—H14E0.9700
C8A—C9A1.463 (4)C14C—H14F0.9700
C9A—C10A1.528 (4)C15C—C16C1.495 (4)
C10A—C11A1.537 (4)C16C—C21C1.383 (4)
C10A—H10A0.9800C16C—C17C1.397 (4)
C11A—C22A1.522 (4)C17C—C18C1.381 (4)
C11A—H11A0.9800C17C—H17C0.9300
C13A—C14A1.491 (4)C18C—C19C1.375 (5)
C14A—H14A0.9700C18C—H18C0.9300
C14A—H14B0.9700C19C—C20C1.380 (5)
C15A—C16A1.501 (4)C19C—H19C0.9300
C16A—C17A1.389 (4)C20C—C21C1.371 (4)
C16A—C21A1.393 (4)C20C—H20C0.9300
C17A—C18A1.384 (4)C21C—H21C0.9300
C17A—H17A0.9300C22C—C27C1.384 (4)
C18A—C19A1.388 (4)C22C—C23C1.394 (4)
C18A—H18A0.9300C23C—C24C1.396 (4)
C19A—C20A1.381 (4)C23C—H23C0.9300
C19A—H19A0.9300C24C—C25C1.379 (5)
C20A—C21A1.378 (4)C24C—H24C0.9300
C20A—H20A0.9300C25C—C26C1.377 (5)
C21A—H21A0.9300C25C—H25C0.9300
C22A—C27A1.386 (4)C26C—C27C1.384 (4)
C22A—C23A1.389 (4)C26C—H26C0.9300
C23A—C24A1.384 (4)C27C—H27C0.9300
C23A—H23A0.9300S1D—C12D1.743 (3)
C24A—C25A1.385 (4)S1D—C10D1.839 (3)
C24A—H24A0.9300O1D—N2D1.365 (4)
C25A—C26A1.373 (4)O1D—C7D1.411 (4)
C25A—H25A0.9300O2D—C7D1.208 (4)
C26A—C27A1.387 (4)O3D—C9D1.222 (3)
C26A—H26A0.9300O4D—C15D1.230 (3)
C27A—H27A0.9300N1D—N2D1.305 (3)
S1B—C12B1.737 (3)N1D—C8D1.353 (4)
S1B—C10B1.855 (3)N1D—C6D1.449 (4)
O1B—N2B1.370 (3)N3D—N4D1.417 (3)
O1B—C7B1.419 (3)N3D—C11D1.481 (4)
O2B—C7B1.208 (4)N3D—H2ND0.95 (4)
O3B—C9B1.215 (3)N4D—C13D1.346 (4)
O4B—C15B1.233 (3)N4D—C12D1.361 (3)
N1B—N2B1.301 (3)N5D—C12D1.306 (4)
N1B—C8B1.364 (4)N5D—N6D1.408 (3)
N1B—C6B1.451 (4)N6D—C13D1.317 (4)
N3B—N4B1.403 (3)N7D—C15D1.339 (4)
N3B—C11B1.491 (4)N7D—C14D1.455 (4)
N3B—H2NB0.88 (3)N7D—H1ND0.89 (3)
N4B—C12B1.358 (3)C1D—C6D1.366 (4)
N4B—C13B1.363 (3)C1D—C2D1.379 (5)
N5B—C12B1.302 (4)C1D—H1DA0.9300
N5B—N6B1.410 (4)C2D—C3D1.386 (5)
N6B—C13B1.298 (4)C2D—H2DA0.9300
N7B—C15B1.346 (4)C3D—C4D1.385 (5)
N7B—C14B1.456 (4)C3D—H3DA0.9300
N7B—H1NB0.86 (3)C4D—C5D1.372 (4)
C1B—C2B1.379 (4)C4D—H4DA0.9300
C1B—C6B1.379 (4)C5D—C6D1.391 (4)
C1B—H1BA0.9300C5D—H5DA0.9300
C2B—C3B1.381 (5)C7D—C8D1.412 (4)
C2B—H2BA0.9300C8D—C9D1.452 (4)
C3B—C4B1.383 (5)C9D—C10D1.526 (4)
C3B—H3BA0.9300C10D—C11D1.537 (4)
C4B—C5B1.384 (5)C10D—H10D0.9800
C4B—H4BA0.9300C11D—C22D1.513 (4)
C5B—C6B1.366 (4)C11D—H11D0.9800
C5B—H5BA0.9300C13D—C14D1.485 (4)
C7B—C8B1.413 (4)C14D—H14G0.9700
C8B—C9B1.449 (4)C14D—H14H0.9700
C9B—C10B1.526 (4)C15D—C16D1.481 (4)
C10B—C11B1.535 (4)C16D—C17D1.381 (4)
C10B—H10B0.9800C16D—C21X1.415 (9)
C11B—C22B1.520 (4)C16D—C21D1.419 (10)
C11B—H11B0.9800C17D—C18D1.382 (4)
C13B—C14B1.480 (4)C17D—H17D0.9300
C14B—H14C0.9700C18D—C19D1.330 (11)
C14B—H14D0.9700C18D—C19X1.460 (13)
C15B—C16B1.492 (4)C18D—H18D0.9300
C16B—C17B1.384 (4)C19D—C20D1.381 (14)
C16B—C21B1.393 (4)C19D—H19D0.9300
C17B—C18B1.383 (4)C20D—C21D1.391 (12)
C17B—H17B0.9300C20D—H20D0.9300
C18B—C19B1.375 (5)C21D—H21D0.9300
C18B—H18B0.9300C19X—C20X1.368 (13)
C19B—C20B1.372 (5)C19X—H19E0.9300
C19B—H19B0.9300C20X—C21X1.392 (12)
C20B—C21B1.382 (5)C20X—H20E0.9300
C20B—H20B0.9300C21X—H21E0.9300
C21B—H21B0.9300C22D—C23D1.380 (4)
C22B—C27B1.385 (4)C22D—C27D1.395 (4)
C22B—C23B1.387 (4)C23D—C24D1.396 (4)
C23B—C24B1.380 (4)C23D—H23D0.9300
C23B—H23B0.9300C24D—C25D1.377 (5)
C24B—C25B1.382 (4)C24D—H24D0.9300
C24B—H24B0.9300C25D—C26D1.368 (5)
C25B—C26B1.372 (4)C25D—H25D0.9300
C25B—H25B0.9300C26D—C27D1.370 (4)
C26B—C27B1.382 (4)C26D—H26D0.9300
C26B—H26B0.9300C27D—H27D0.9300
C27B—H27B0.9300O1W—H1W10.8515
S1C—C12C1.740 (3)O1W—H2W10.8514
C12A—S1A—C10A99.95 (12)N2C—O1C—C7C110.3 (2)
N3A—O1A—C7A110.6 (2)N2C—N1C—C8C114.7 (3)
N3A—N1A—C8A114.1 (3)N2C—N1C—C6C116.4 (3)
N3A—N1A—C6A116.0 (2)C8C—N1C—C6C128.8 (3)
C8A—N1A—C6A129.7 (3)N1C—N2C—O1C105.1 (2)
N4A—N2A—C11A109.0 (2)N4C—N3C—C11C109.9 (2)
N4A—N2A—H2NA109 (2)N4C—N3C—H2NC107.0 (19)
C11A—N2A—H2NA110 (2)C11C—N3C—H2NC105.9 (19)
N1A—N3A—O1A105.5 (2)C12C—N4C—C13C106.1 (2)
C12A—N4A—C13A105.9 (2)C12C—N4C—N3C128.9 (2)
C12A—N4A—N2A128.2 (2)C13C—N4C—N3C124.6 (2)
C13A—N4A—N2A125.6 (2)C12C—N5C—N6C105.9 (2)
C12A—N5A—N6A106.0 (2)C13C—N6C—N5C107.9 (2)
C13A—N6A—N5A108.4 (2)C15C—N7C—C14C120.1 (3)
C15A—N7A—C14A121.3 (3)C15C—N7C—H1NC123 (2)
C15A—N7A—H1NA122 (2)C14C—N7C—H1NC116 (2)
C14A—N7A—H1NA116 (2)C6C—C1C—C2C118.5 (3)
C6A—C1A—C2A112.8 (8)C6C—C1C—H1CA120.8
C6A—C1A—H1AA123.6C2C—C1C—H1CA120.8
C2A—C1A—H1AA123.6C3C—C2C—C1C120.5 (4)
C3A—C2A—C1A121.7 (10)C3C—C2C—H2CA119.8
C3A—C2A—H2AA119.2C1C—C2C—H2CA119.8
C1A—C2A—H2AA119.2C2C—C3C—C4C119.8 (4)
C2A—C3A—C4A123.4 (11)C2C—C3C—H3CA120.1
C2A—C3A—H3AA118.3C4C—C3C—H3CA120.1
C4A—C3A—H3AA118.3C3C—C4C—C5C120.6 (3)
C2X—C1X—C6A122.1 (7)C3C—C4C—H4CA119.7
C2X—C1X—H1XA119.0C5C—C4C—H4CA119.7
C6A—C1X—H1XA119.0C6C—C5C—C4C117.9 (3)
C3X—C2X—C1X119.8 (10)C6C—C5C—H5CA121.0
C3X—C2X—H2XA120.1C4C—C5C—H5CA121.0
C1X—C2X—H2XA120.1C1C—C6C—C5C122.7 (3)
C4A—C3X—C2X117.4 (13)C1C—C6C—N1C118.3 (3)
C4A—C3X—H3XA121.3C5C—C6C—N1C118.9 (3)
C2X—C3X—H3XA121.3O2C—C7C—C8C135.7 (3)
C3X—C4A—C5A125.2 (8)O2C—C7C—O1C120.0 (3)
C3X—C4A—C3A22.9 (7)C8C—C7C—O1C104.3 (3)
C5A—C4A—C3A113.2 (7)N1C—C8C—C7C105.6 (3)
C3X—C4A—H4AA108.2N1C—C8C—C9C124.7 (3)
C5A—C4A—H4AA123.4C7C—C8C—C9C127.8 (3)
C3A—C4A—H4AA123.4O3C—C9C—C8C123.6 (3)
C6A—C5A—C4A119.2 (3)O3C—C9C—C10C122.0 (3)
C6A—C5A—H5AA120.4C8C—C9C—C10C114.4 (3)
C4A—C5A—H5AA120.4C9C—C10C—C11C112.0 (2)
C5A—C6A—C1A127.7 (5)C9C—C10C—S1C108.24 (18)
C5A—C6A—C1X114.1 (5)C11C—C10C—S1C115.31 (18)
C1A—C6A—C1X32.9 (5)C9C—C10C—H10C106.9
C5A—C6A—N1A118.9 (3)C11C—C10C—H10C106.9
C1A—C6A—N1A110.3 (6)S1C—C10C—H10C106.9
C1X—C6A—N1A125.5 (4)N3C—C11C—C22C110.9 (2)
O2A—C7A—C8A135.7 (3)N3C—C11C—C10C113.5 (2)
O2A—C7A—O1A120.1 (3)C22C—C11C—C10C115.5 (2)
C8A—C7A—O1A104.2 (2)N3C—C11C—H11C105.3
N1A—C8A—C7A105.5 (3)C22C—C11C—H11C105.3
N1A—C8A—C9A126.0 (3)C10C—C11C—H11C105.3
C7A—C8A—C9A128.4 (3)N5C—C12C—N4C110.8 (3)
O3A—C9A—C8A122.8 (3)N5C—C12C—S1C124.9 (2)
O3A—C9A—C10A122.7 (3)N4C—C12C—S1C123.9 (2)
C8A—C9A—C10A114.5 (2)N6C—C13C—N4C109.3 (3)
C9A—C10A—C11A111.6 (2)N6C—C13C—C14C126.3 (3)
C9A—C10A—S1A107.49 (18)N4C—C13C—C14C124.3 (3)
C11A—C10A—S1A114.83 (18)N7C—C14C—C13C111.7 (2)
C9A—C10A—H10A107.5N7C—C14C—H14E109.3
C11A—C10A—H10A107.5C13C—C14C—H14E109.3
S1A—C10A—H10A107.5N7C—C14C—H14F109.3
N2A—C11A—C22A109.3 (2)C13C—C14C—H14F109.3
N2A—C11A—C10A113.9 (2)H14E—C14C—H14F107.9
C22A—C11A—C10A115.4 (2)O4C—C15C—N7C122.0 (3)
N2A—C11A—H11A105.8O4C—C15C—C16C121.8 (3)
C22A—C11A—H11A105.8N7C—C15C—C16C116.2 (2)
C10A—C11A—H11A105.8C21C—C16C—C17C120.1 (3)
N5A—C12A—N4A110.5 (2)C21C—C16C—C15C117.6 (3)
N5A—C12A—S1A124.6 (2)C17C—C16C—C15C122.3 (3)
N4A—C12A—S1A124.68 (19)C18C—C17C—C16C118.6 (3)
N6A—C13A—N4A109.1 (2)C18C—C17C—H17C120.7
N6A—C13A—C14A126.8 (3)C16C—C17C—H17C120.7
N4A—C13A—C14A124.0 (2)C19C—C18C—C17C120.6 (3)
N7A—C14A—C13A112.6 (3)C19C—C18C—H18C119.7
N7A—C14A—H14A109.1C17C—C18C—H18C119.7
C13A—C14A—H14A109.1C18C—C19C—C20C120.7 (3)
N7A—C14A—H14B109.1C18C—C19C—H19C119.6
C13A—C14A—H14B109.1C20C—C19C—H19C119.6
H14A—C14A—H14B107.8C21C—C20C—C19C119.2 (3)
O4A—C15A—N7A121.9 (3)C21C—C20C—H20C120.4
O4A—C15A—C16A121.3 (2)C19C—C20C—H20C120.4
N7A—C15A—C16A116.8 (3)C20C—C21C—C16C120.7 (3)
C17A—C16A—C21A119.5 (3)C20C—C21C—H21C119.7
C17A—C16A—C15A123.4 (3)C16C—C21C—H21C119.7
C21A—C16A—C15A117.1 (3)C27C—C22C—C23C118.5 (3)
C18A—C17A—C16A120.0 (3)C27C—C22C—C11C117.7 (3)
C18A—C17A—H17A120.0C23C—C22C—C11C123.7 (3)
C16A—C17A—H17A120.0C22C—C23C—C24C120.2 (3)
C17A—C18A—C19A120.0 (3)C22C—C23C—H23C119.9
C17A—C18A—H18A120.0C24C—C23C—H23C119.9
C19A—C18A—H18A120.0C25C—C24C—C23C120.2 (3)
C20A—C19A—C18A120.2 (3)C25C—C24C—H24C119.9
C20A—C19A—H19A119.9C23C—C24C—H24C119.9
C18A—C19A—H19A119.9C26C—C25C—C24C119.8 (3)
C21A—C20A—C19A120.0 (3)C26C—C25C—H25C120.1
C21A—C20A—H20A120.0C24C—C25C—H25C120.1
C19A—C20A—H20A120.0C25C—C26C—C27C120.2 (3)
C20A—C21A—C16A120.4 (3)C25C—C26C—H26C119.9
C20A—C21A—H21A119.8C27C—C26C—H26C119.9
C16A—C21A—H21A119.8C26C—C27C—C22C121.1 (3)
C27A—C22A—C23A118.8 (3)C26C—C27C—H27C119.4
C27A—C22A—C11A123.5 (2)C22C—C27C—H27C119.4
C23A—C22A—C11A117.6 (2)C12D—S1D—C10D100.30 (13)
C24A—C23A—C22A120.7 (3)N2D—O1D—C7D110.6 (2)
C24A—C23A—H23A119.7N2D—N1D—C8D113.7 (3)
C22A—C23A—H23A119.7N2D—N1D—C6D116.9 (2)
C23A—C24A—C25A119.9 (3)C8D—N1D—C6D129.3 (2)
C23A—C24A—H24A120.1N1D—N2D—O1D105.7 (2)
C25A—C24A—H24A120.1N4D—N3D—C11D109.9 (2)
C26A—C25A—C24A119.8 (3)N4D—N3D—H2ND112 (2)
C26A—C25A—H25A120.1C11D—N3D—H2ND101 (2)
C24A—C25A—H25A120.1C13D—N4D—C12D105.9 (2)
C25A—C26A—C27A120.4 (3)C13D—N4D—N3D125.5 (2)
C25A—C26A—H26A119.8C12D—N4D—N3D128.3 (2)
C27A—C26A—H26A119.8C12D—N5D—N6D106.2 (2)
C22A—C27A—C26A120.3 (3)C13D—N6D—N5D107.2 (2)
C22A—C27A—H27A119.8C15D—N7D—C14D120.3 (2)
C26A—C27A—H27A119.8C15D—N7D—H1ND121.1 (19)
C12B—S1B—C10B99.92 (12)C14D—N7D—H1ND118.6 (19)
N2B—O1B—C7B110.6 (2)C6D—C1D—C2D117.8 (3)
N2B—N1B—C8B114.6 (2)C6D—C1D—H1DA121.1
N2B—N1B—C6B116.3 (2)C2D—C1D—H1DA121.1
C8B—N1B—C6B128.7 (2)C1D—C2D—C3D120.9 (3)
N1B—N2B—O1B105.2 (2)C1D—C2D—H2DA119.5
N4B—N3B—C11B107.7 (2)C3D—C2D—H2DA119.5
N4B—N3B—H2NB102 (2)C4D—C3D—C2D120.0 (4)
C11B—N3B—H2NB111 (2)C4D—C3D—H3DA120.0
C12B—N4B—C13B105.9 (2)C2D—C3D—H3DA120.0
C12B—N4B—N3B127.2 (2)C5D—C4D—C3D119.8 (3)
C13B—N4B—N3B126.2 (2)C5D—C4D—H4DA120.1
C12B—N5B—N6B106.8 (2)C3D—C4D—H4DA120.1
C13B—N6B—N5B107.2 (2)C4D—C5D—C6D118.7 (3)
C15B—N7B—C14B120.2 (2)C4D—C5D—H5DA120.7
C15B—N7B—H1NB122 (2)C6D—C5D—H5DA120.7
C14B—N7B—H1NB117 (2)C1D—C6D—C5D122.7 (3)
C2B—C1B—C6B117.7 (3)C1D—C6D—N1D119.0 (3)
C2B—C1B—H1BA121.1C5D—C6D—N1D118.3 (3)
C6B—C1B—H1BA121.1O2D—C7D—O1D120.2 (3)
C1B—C2B—C3B120.4 (3)O2D—C7D—C8D136.1 (3)
C1B—C2B—H2BA119.8O1D—C7D—C8D103.6 (3)
C3B—C2B—H2BA119.8N1D—C8D—C7D106.4 (2)
C2B—C3B—C4B120.3 (3)N1D—C8D—C9D124.0 (3)
C2B—C3B—H3BA119.8C7D—C8D—C9D129.3 (3)
C4B—C3B—H3BA119.8O3D—C9D—C8D122.3 (3)
C3B—C4B—C5B120.1 (3)O3D—C9D—C10D122.1 (3)
C3B—C4B—H4BA119.9C8D—C9D—C10D115.6 (3)
C5B—C4B—H4BA119.9C9D—C10D—C11D110.2 (2)
C6B—C5B—C4B118.0 (3)C9D—C10D—S1D108.08 (18)
C6B—C5B—H5BA121.0C11D—C10D—S1D115.69 (19)
C4B—C5B—H5BA121.0C9D—C10D—H10D107.5
C5B—C6B—C1B123.4 (3)C11D—C10D—H10D107.5
C5B—C6B—N1B118.9 (3)S1D—C10D—H10D107.5
C1B—C6B—N1B117.3 (3)N3D—C11D—C22D110.1 (2)
O2B—C7B—C8B135.6 (3)N3D—C11D—C10D113.1 (2)
O2B—C7B—O1B120.5 (3)C22D—C11D—C10D115.6 (2)
C8B—C7B—O1B103.9 (3)N3D—C11D—H11D105.7
N1B—C8B—C7B105.6 (2)C22D—C11D—H11D105.7
N1B—C8B—C9B125.3 (2)C10D—C11D—H11D105.7
C7B—C8B—C9B129.0 (3)N5D—C12D—N4D110.7 (2)
O3B—C9B—C8B121.9 (3)N5D—C12D—S1D124.9 (2)
O3B—C9B—C10B122.4 (2)N4D—C12D—S1D124.2 (2)
C8B—C9B—C10B115.7 (2)N6D—C13D—N4D109.9 (2)
C9B—C10B—C11B111.1 (2)N6D—C13D—C14D125.6 (3)
C9B—C10B—S1B108.09 (18)N4D—C13D—C14D124.4 (3)
C11B—C10B—S1B113.84 (18)N7D—C14D—C13D112.0 (2)
C9B—C10B—H10B107.9N7D—C14D—H14G109.2
C11B—C10B—H10B107.9C13D—C14D—H14G109.2
S1B—C10B—H10B107.9N7D—C14D—H14H109.2
N3B—C11B—C22B108.9 (2)C13D—C14D—H14H109.2
N3B—C11B—C10B112.6 (2)H14G—C14D—H14H107.9
C22B—C11B—C10B115.1 (2)O4D—C15D—N7D121.8 (3)
N3B—C11B—H11B106.6O4D—C15D—C16D121.1 (3)
C22B—C11B—H11B106.6N7D—C15D—C16D117.1 (2)
C10B—C11B—H11B106.6C17D—C16D—C21X121.5 (5)
N5B—C12B—N4B110.1 (2)C17D—C16D—C21D113.3 (5)
N5B—C12B—S1B125.6 (2)C21X—C16D—C21D29.4 (4)
N4B—C12B—S1B124.2 (2)C17D—C16D—C15D124.2 (3)
N6B—C13B—N4B109.9 (2)C21X—C16D—C15D111.7 (5)
N6B—C13B—C14B126.6 (3)C21D—C16D—C15D121.3 (4)
N4B—C13B—C14B123.4 (3)C16D—C17D—C18D121.0 (3)
N7B—C14B—C13B110.8 (2)C16D—C17D—H17D119.5
N7B—C14B—H14C109.5C18D—C17D—H17D119.5
C13B—C14B—H14C109.5C19D—C18D—C17D124.0 (6)
N7B—C14B—H14D109.5C19D—C18D—C19X28.6 (4)
C13B—C14B—H14D109.5C17D—C18D—C19X115.3 (5)
H14C—C14B—H14D108.1C19D—C18D—H18D118.0
O4B—C15B—N7B121.9 (3)C17D—C18D—H18D118.0
O4B—C15B—C16B120.9 (3)C19X—C18D—H18D118.6
N7B—C15B—C16B117.3 (2)C18D—C19D—C20D116.5 (9)
C17B—C16B—C21B119.4 (3)C18D—C19D—H19D121.8
C17B—C16B—C15B123.4 (2)C20D—C19D—H19D121.8
C21B—C16B—C15B117.1 (3)C19D—C20D—C21D120.3 (8)
C18B—C17B—C16B120.1 (3)C19D—C20D—H20D119.9
C18B—C17B—H17B120.0C21D—C20D—H20D119.9
C16B—C17B—H17B120.0C20D—C21D—C16D123.0 (7)
C19B—C18B—C17B119.9 (3)C20D—C21D—H21D118.5
C19B—C18B—H18B120.1C16D—C21D—H21D118.5
C17B—C18B—H18B120.1C20X—C19X—C18D122.2 (8)
C20B—C19B—C18B120.9 (3)C20X—C19X—H19E118.9
C20B—C19B—H19B119.6C18D—C19X—H19E118.9
C18B—C19B—H19B119.6C19X—C20X—C21X120.8 (8)
C19B—C20B—C21B119.6 (3)C19X—C20X—H20E119.6
C19B—C20B—H20B120.2C21X—C20X—H20E119.6
C21B—C20B—H20B120.2C20X—C21X—C16D117.0 (7)
C20B—C21B—C16B120.2 (3)C20X—C21X—H21E121.5
C20B—C21B—H21B119.9C16D—C21X—H21E121.5
C16B—C21B—H21B119.9C23D—C22D—C27D118.2 (3)
C27B—C22B—C23B117.9 (3)C23D—C22D—C11D124.9 (3)
C27B—C22B—C11B123.6 (2)C27D—C22D—C11D116.8 (3)
C23B—C22B—C11B118.4 (2)C22D—C23D—C24D120.5 (3)
C24B—C23B—C22B121.3 (3)C22D—C23D—H23D119.7
C24B—C23B—H23B119.3C24D—C23D—H23D119.7
C22B—C23B—H23B119.3C25D—C24D—C23D119.6 (3)
C23B—C24B—C25B119.8 (3)C25D—C24D—H24D120.2
C23B—C24B—H24B120.1C23D—C24D—H24D120.2
C25B—C24B—H24B120.1C26D—C25D—C24D120.4 (3)
C26B—C25B—C24B119.7 (3)C26D—C25D—H25D119.8
C26B—C25B—H25B120.1C24D—C25D—H25D119.8
C24B—C25B—H25B120.1C25D—C26D—C27D119.9 (3)
C25B—C26B—C27B120.2 (3)C25D—C26D—H26D120.0
C25B—C26B—H26B119.9C27D—C26D—H26D120.0
C27B—C26B—H26B119.9C26D—C27D—C22D121.3 (3)
C26B—C27B—C22B121.0 (3)C26D—C27D—H27D119.4
C26B—C27B—H27B119.5C22D—C27D—H27D119.4
C22B—C27B—H27B119.5H1W1—O1W—H2W1125.3
C12C—S1C—C10C100.08 (13)
C8A—N1A—N3A—O1A0.7 (3)C8C—N1C—N2C—O1C0.8 (3)
C6A—N1A—N3A—O1A176.5 (2)C6C—N1C—N2C—O1C178.5 (2)
C7A—O1A—N3A—N1A1.1 (3)C7C—O1C—N2C—N1C0.8 (3)
C11A—N2A—N4A—C12A37.1 (4)C11C—N3C—N4C—C12C39.7 (3)
C11A—N2A—N4A—C13A136.8 (3)C11C—N3C—N4C—C13C148.7 (2)
C12A—N5A—N6A—C13A1.1 (3)C12C—N5C—N6C—C13C0.3 (3)
C6A—C1A—C2A—C3A4.8 (12)C6C—C1C—C2C—C3C1.0 (5)
C1A—C2A—C3A—C4A2.1 (17)C1C—C2C—C3C—C4C0.5 (5)
C6A—C1X—C2X—C3X6.0 (19)C2C—C3C—C4C—C5C0.6 (5)
C1X—C2X—C3X—C4A0.7 (18)C3C—C4C—C5C—C6C1.1 (5)
C2X—C3X—C4A—C5A4.6 (15)C2C—C1C—C6C—C5C0.4 (5)
C2X—C3X—C4A—C3A60 (3)C2C—C1C—C6C—N1C179.0 (3)
C2A—C3A—C4A—C3X127 (4)C4C—C5C—C6C—C1C0.6 (5)
C2A—C3A—C4A—C5A0.3 (14)C4C—C5C—C6C—N1C180.0 (3)
C3X—C4A—C5A—C6A13.8 (10)N2C—N1C—C6C—C1C69.2 (4)
C3A—C4A—C5A—C6A8.6 (7)C8C—N1C—C6C—C1C108.0 (3)
C4A—C5A—C6A—C1A18.0 (8)N2C—N1C—C6C—C5C110.2 (3)
C4A—C5A—C6A—C1X17.2 (9)C8C—N1C—C6C—C5C72.6 (4)
C4A—C5A—C6A—N1A176.2 (3)N2C—O1C—C7C—O2C179.6 (3)
C2A—C1A—C6A—C5A15.4 (9)N2C—O1C—C7C—C8C0.4 (3)
C2A—C1A—C6A—C1X60.5 (12)N2C—N1C—C8C—C7C0.6 (3)
C2A—C1A—C6A—N1A175.1 (5)C6C—N1C—C8C—C7C177.8 (3)
C2X—C1X—C6A—C5A14.1 (14)N2C—N1C—C8C—C9C164.8 (3)
C2X—C1X—C6A—C1A108.7 (19)C6C—N1C—C8C—C9C12.5 (5)
C2X—C1X—C6A—N1A179.7 (8)O2C—C7C—C8C—N1C178.9 (3)
N3A—N1A—C6A—C5A108.2 (3)O1C—C7C—C8C—N1C0.1 (3)
C8A—N1A—C6A—C5A66.7 (4)O2C—C7C—C8C—C9C16.3 (6)
N3A—N1A—C6A—C1A53.5 (5)O1C—C7C—C8C—C9C164.7 (3)
C8A—N1A—C6A—C1A131.6 (5)N1C—C8C—C9C—O3C17.4 (4)
N3A—N1A—C6A—C1X86.8 (10)C7C—C8C—C9C—O3C179.5 (3)
C8A—N1A—C6A—C1X98.2 (10)N1C—C8C—C9C—C10C160.6 (3)
N3A—O1A—C7A—O2A179.9 (2)C7C—C8C—C9C—C10C1.4 (4)
N3A—O1A—C7A—C8A1.0 (3)O3C—C9C—C10C—C11C28.2 (3)
N3A—N1A—C8A—C7A0.1 (3)C8C—C9C—C10C—C11C149.9 (2)
C6A—N1A—C8A—C7A175.1 (3)O3C—C9C—C10C—S1C100.0 (3)
N3A—N1A—C8A—C9A177.8 (3)C8C—C9C—C10C—S1C81.9 (3)
C6A—N1A—C8A—C9A2.8 (5)C12C—S1C—C10C—C9C99.4 (2)
O2A—C7A—C8A—N1A179.5 (3)C12C—S1C—C10C—C11C27.0 (2)
O1A—C7A—C8A—N1A0.6 (3)N4C—N3C—C11C—C22C72.8 (3)
O2A—C7A—C8A—C9A2.7 (6)N4C—N3C—C11C—C10C59.2 (3)
O1A—C7A—C8A—C9A178.4 (3)C9C—C10C—C11C—N3C68.1 (3)
N1A—C8A—C9A—O3A13.6 (4)S1C—C10C—C11C—N3C56.3 (3)
C7A—C8A—C9A—O3A169.0 (3)C9C—C10C—C11C—C22C162.2 (2)
N1A—C8A—C9A—C10A167.3 (3)S1C—C10C—C11C—C22C73.4 (3)
C7A—C8A—C9A—C10A10.2 (4)N6C—N5C—C12C—N4C0.0 (3)
O3A—C9A—C10A—C11A28.4 (3)N6C—N5C—C12C—S1C172.69 (19)
C8A—C9A—C10A—C11A152.5 (2)C13C—N4C—C12C—N5C0.4 (3)
O3A—C9A—C10A—S1A98.4 (3)N3C—N4C—C12C—N5C172.4 (2)
C8A—C9A—C10A—S1A80.8 (2)C13C—N4C—C12C—S1C172.4 (2)
C12A—S1A—C10A—C9A107.6 (2)N3C—N4C—C12C—S1C14.8 (4)
C12A—S1A—C10A—C11A17.2 (2)C10C—S1C—C12C—N5C178.7 (2)
N4A—N2A—C11A—C22A67.7 (3)C10C—S1C—C12C—N4C6.9 (3)
N4A—N2A—C11A—C10A63.0 (3)N5C—N6C—C13C—N4C0.6 (3)
C9A—C10A—C11A—N2A68.3 (3)N5C—N6C—C13C—C14C176.8 (3)
S1A—C10A—C11A—N2A54.3 (3)C12C—N4C—C13C—N6C0.6 (3)
C9A—C10A—C11A—C22A164.0 (2)N3C—N4C—C13C—N6C172.6 (2)
S1A—C10A—C11A—C22A73.4 (3)C12C—N4C—C13C—C14C176.8 (2)
N6A—N5A—C12A—N4A0.3 (3)N3C—N4C—C13C—C14C10.0 (4)
N6A—N5A—C12A—S1A174.8 (2)C15C—N7C—C14C—C13C156.7 (3)
C13A—N4A—C12A—N5A1.6 (3)N6C—C13C—C14C—N7C107.1 (3)
N2A—N4A—C12A—N5A176.4 (2)N4C—C13C—C14C—N7C75.9 (3)
C13A—N4A—C12A—S1A173.5 (2)C14C—N7C—C15C—O4C5.8 (4)
N2A—N4A—C12A—S1A1.3 (4)C14C—N7C—C15C—C16C174.1 (2)
C10A—S1A—C12A—N5A166.2 (2)O4C—C15C—C16C—C21C23.4 (4)
C10A—S1A—C12A—N4A8.2 (3)N7C—C15C—C16C—C21C156.5 (3)
N5A—N6A—C13A—N4A2.1 (3)O4C—C15C—C16C—C17C157.9 (3)
N5A—N6A—C13A—C14A175.1 (3)N7C—C15C—C16C—C17C22.2 (4)
C12A—N4A—C13A—N6A2.3 (3)C21C—C16C—C17C—C18C1.7 (4)
N2A—N4A—C13A—N6A177.3 (2)C15C—C16C—C17C—C18C177.0 (3)
C12A—N4A—C13A—C14A175.0 (3)C16C—C17C—C18C—C19C0.2 (5)
N2A—N4A—C13A—C14A0.1 (4)C17C—C18C—C19C—C20C1.7 (5)
C15A—N7A—C14A—C13A147.6 (3)C18C—C19C—C20C—C21C1.3 (5)
N6A—C13A—C14A—N7A119.2 (3)C19C—C20C—C21C—C16C0.6 (5)
N4A—C13A—C14A—N7A63.9 (4)C17C—C16C—C21C—C20C2.1 (4)
C14A—N7A—C15A—O4A3.0 (4)C15C—C16C—C21C—C20C176.7 (3)
C14A—N7A—C15A—C16A176.7 (2)N3C—C11C—C22C—C27C53.3 (3)
O4A—C15A—C16A—C17A158.2 (3)C10C—C11C—C22C—C27C175.8 (2)
N7A—C15A—C16A—C17A22.1 (4)N3C—C11C—C22C—C23C131.0 (3)
O4A—C15A—C16A—C21A20.1 (4)C10C—C11C—C22C—C23C0.1 (4)
N7A—C15A—C16A—C21A159.5 (3)C27C—C22C—C23C—C24C0.3 (4)
C21A—C16A—C17A—C18A0.6 (4)C11C—C22C—C23C—C24C175.3 (3)
C15A—C16A—C17A—C18A178.9 (3)C22C—C23C—C24C—C25C0.1 (5)
C16A—C17A—C18A—C19A0.7 (4)C23C—C24C—C25C—C26C0.0 (5)
C17A—C18A—C19A—C20A0.5 (5)C24C—C25C—C26C—C27C0.6 (5)
C18A—C19A—C20A—C21A0.9 (5)C25C—C26C—C27C—C22C1.0 (5)
C19A—C20A—C21A—C16A2.2 (4)C23C—C22C—C27C—C26C0.9 (4)
C17A—C16A—C21A—C20A2.0 (4)C11C—C22C—C27C—C26C175.0 (3)
C15A—C16A—C21A—C20A179.5 (2)C8D—N1D—N2D—O1D1.0 (3)
N2A—C11A—C22A—C27A129.5 (3)C6D—N1D—N2D—O1D177.6 (2)
C10A—C11A—C22A—C27A0.4 (4)C7D—O1D—N2D—N1D1.2 (3)
N2A—C11A—C22A—C23A52.1 (3)C11D—N3D—N4D—C13D146.4 (2)
C10A—C11A—C22A—C23A178.0 (2)C11D—N3D—N4D—C12D40.0 (3)
C27A—C22A—C23A—C24A1.5 (4)C12D—N5D—N6D—C13D0.7 (3)
C11A—C22A—C23A—C24A177.0 (2)C6D—C1D—C2D—C3D1.2 (5)
C22A—C23A—C24A—C25A0.6 (4)C1D—C2D—C3D—C4D1.0 (5)
C23A—C24A—C25A—C26A0.7 (4)C2D—C3D—C4D—C5D0.5 (5)
C24A—C25A—C26A—C27A1.0 (4)C3D—C4D—C5D—C6D1.7 (4)
C23A—C22A—C27A—C26A1.1 (4)C2D—C1D—C6D—C5D0.1 (5)
C11A—C22A—C27A—C26A177.3 (2)C2D—C1D—C6D—N1D177.5 (3)
C25A—C26A—C27A—C22A0.2 (4)C4D—C5D—C6D—C1D1.6 (4)
C8B—N1B—N2B—O1B0.8 (3)C4D—C5D—C6D—N1D176.1 (3)
C6B—N1B—N2B—O1B174.5 (2)N2D—N1D—C6D—C1D67.2 (4)
C7B—O1B—N2B—N1B2.1 (3)C8D—N1D—C6D—C1D116.8 (3)
C11B—N3B—N4B—C12B37.3 (3)N2D—N1D—C6D—C5D110.6 (3)
C11B—N3B—N4B—C13B132.2 (3)C8D—N1D—C6D—C5D65.4 (4)
C12B—N5B—N6B—C13B1.5 (3)N2D—O1D—C7D—O2D179.3 (3)
C6B—C1B—C2B—C3B0.4 (4)N2D—O1D—C7D—C8D0.9 (3)
C1B—C2B—C3B—C4B1.4 (5)N2D—N1D—C8D—C7D0.5 (3)
C2B—C3B—C4B—C5B2.2 (6)C6D—N1D—C8D—C7D176.6 (3)
C3B—C4B—C5B—C6B1.9 (5)N2D—N1D—C8D—C9D174.9 (3)
C4B—C5B—C6B—C1B0.9 (5)C6D—N1D—C8D—C9D9.1 (4)
C4B—C5B—C6B—N1B174.2 (3)O2D—C7D—C8D—N1D178.3 (3)
C2B—C1B—C6B—C5B0.1 (4)O1D—C7D—C8D—N1D0.2 (3)
C2B—C1B—C6B—N1B173.5 (2)O2D—C7D—C8D—C9D4.4 (6)
N2B—N1B—C6B—C5B60.3 (4)O1D—C7D—C8D—C9D173.7 (3)
C8B—N1B—C6B—C5B127.1 (3)N1D—C8D—C9D—O3D5.7 (4)
N2B—N1B—C6B—C1B113.4 (3)C7D—C8D—C9D—O3D167.3 (3)
C8B—N1B—C6B—C1B59.2 (4)N1D—C8D—C9D—C10D176.2 (2)
N2B—O1B—C7B—O2B178.6 (3)C7D—C8D—C9D—C10D10.8 (4)
N2B—O1B—C7B—C8B2.6 (3)O3D—C9D—C10D—C11D22.8 (4)
N2B—N1B—C8B—C7B0.8 (3)C8D—C9D—C10D—C11D159.2 (2)
C6B—N1B—C8B—C7B172.0 (3)O3D—C9D—C10D—S1D104.5 (3)
N2B—N1B—C8B—C9B176.1 (3)C8D—C9D—C10D—S1D73.5 (3)
C6B—N1B—C8B—C9B11.2 (4)C12D—S1D—C10D—C9D100.4 (2)
O2B—C7B—C8B—N1B179.4 (3)C12D—S1D—C10D—C11D23.7 (2)
O1B—C7B—C8B—N1B2.0 (3)N4D—N3D—C11D—C22D70.3 (3)
O2B—C7B—C8B—C9B3.9 (6)N4D—N3D—C11D—C10D60.6 (3)
O1B—C7B—C8B—C9B174.7 (3)C9D—C10D—C11D—N3D67.7 (3)
N1B—C8B—C9B—O3B11.3 (4)S1D—C10D—C11D—N3D55.2 (3)
C7B—C8B—C9B—O3B164.8 (3)C9D—C10D—C11D—C22D164.1 (2)
N1B—C8B—C9B—C10B170.1 (2)S1D—C10D—C11D—C22D73.0 (3)
C7B—C8B—C9B—C10B13.7 (4)N6D—N5D—C12D—N4D0.1 (3)
O3B—C9B—C10B—C11B22.9 (4)N6D—N5D—C12D—S1D174.59 (19)
C8B—C9B—C10B—C11B158.5 (2)C13D—N4D—C12D—N5D0.5 (3)
O3B—C9B—C10B—S1B102.7 (3)N3D—N4D—C12D—N5D174.1 (2)
C8B—C9B—C10B—S1B75.9 (3)C13D—N4D—C12D—S1D174.1 (2)
C12B—S1B—C10B—C9B111.58 (19)N3D—N4D—C12D—S1D11.4 (4)
C12B—S1B—C10B—C11B12.4 (2)C10D—S1D—C12D—N5D176.0 (2)
N4B—N3B—C11B—C22B61.3 (3)C10D—S1D—C12D—N4D2.2 (3)
N4B—N3B—C11B—C10B67.6 (3)N5D—N6D—C13D—N4D1.0 (3)
C9B—C10B—C11B—N3B67.5 (3)N5D—N6D—C13D—C14D178.2 (3)
S1B—C10B—C11B—N3B54.9 (3)C12D—N4D—C13D—N6D0.9 (3)
C9B—C10B—C11B—C22B166.9 (2)N3D—N4D—C13D—N6D173.9 (2)
S1B—C10B—C11B—C22B70.7 (3)C12D—N4D—C13D—C14D178.3 (3)
N6B—N5B—C12B—N4B0.6 (3)N3D—N4D—C13D—C14D7.0 (4)
N6B—N5B—C12B—S1B178.3 (2)C15D—N7D—C14D—C13D152.5 (3)
C13B—N4B—C12B—N5B0.5 (3)N6D—C13D—C14D—N7D106.9 (3)
N3B—N4B—C12B—N5B171.7 (2)N4D—C13D—C14D—N7D74.1 (4)
C13B—N4B—C12B—S1B177.3 (2)C14D—N7D—C15D—O4D1.0 (4)
N3B—N4B—C12B—S1B6.0 (4)C14D—N7D—C15D—C16D177.7 (3)
C10B—S1B—C12B—N5B160.1 (2)O4D—C15D—C16D—C17D159.1 (3)
C10B—S1B—C12B—N4B17.3 (3)N7D—C15D—C16D—C17D22.2 (4)
N5B—N6B—C13B—N4B1.8 (3)O4D—C15D—C16D—C21X3.0 (6)
N5B—N6B—C13B—C14B179.0 (3)N7D—C15D—C16D—C21X175.7 (6)
C12B—N4B—C13B—N6B1.4 (3)O4D—C15D—C16D—C21D34.2 (8)
N3B—N4B—C13B—N6B172.8 (2)N7D—C15D—C16D—C21D144.5 (8)
C12B—N4B—C13B—C14B178.7 (3)C21X—C16D—C17D—C18D17.9 (7)
N3B—N4B—C13B—C14B9.9 (4)C21D—C16D—C17D—C18D14.1 (8)
C15B—N7B—C14B—C13B155.4 (3)C15D—C16D—C17D—C18D178.3 (3)
N6B—C13B—C14B—N7B112.6 (3)C16D—C17D—C18D—C19D17.4 (9)
N4B—C13B—C14B—N7B64.2 (4)C16D—C17D—C18D—C19X14.2 (8)
C14B—N7B—C15B—O4B1.8 (4)C17D—C18D—C19D—C20D10.5 (12)
C14B—N7B—C15B—C16B176.7 (2)C19X—C18D—C19D—C20D70.4 (16)
O4B—C15B—C16B—C17B153.5 (3)C18D—C19D—C20D—C21D2.3 (14)
N7B—C15B—C16B—C17B25.1 (4)C19D—C20D—C21D—C16D0.8 (15)
O4B—C15B—C16B—C21B22.7 (4)C17D—C16D—C21D—C20D6.5 (12)
N7B—C15B—C16B—C21B158.8 (3)C21X—C16D—C21D—C20D106.8 (17)
C21B—C16B—C17B—C18B0.4 (4)C15D—C16D—C21D—C20D174.5 (7)
C15B—C16B—C17B—C18B175.7 (3)C19D—C18D—C19X—C20X108 (2)
C16B—C17B—C18B—C19B0.7 (5)C17D—C18D—C19X—C20X6.9 (13)
C17B—C18B—C19B—C20B0.3 (5)C18D—C19X—C20X—C21X2.7 (16)
C18B—C19B—C20B—C21B0.5 (6)C19X—C20X—C21X—C16D5.3 (13)
C19B—C20B—C21B—C16B0.9 (5)C17D—C16D—C21X—C20X12.7 (10)
C17B—C16B—C21B—C20B0.5 (5)C21D—C16D—C21X—C20X69.1 (12)
C15B—C16B—C21B—C20B176.7 (3)C15D—C16D—C21X—C20X175.3 (6)
N3B—C11B—C22B—C27B130.5 (3)N3D—C11D—C22D—C23D126.5 (3)
C10B—C11B—C22B—C27B3.0 (4)C10D—C11D—C22D—C23D3.2 (4)
N3B—C11B—C22B—C23B48.9 (3)N3D—C11D—C22D—C27D56.1 (3)
C10B—C11B—C22B—C23B176.5 (2)C10D—C11D—C22D—C27D174.3 (2)
C27B—C22B—C23B—C24B0.5 (4)C27D—C22D—C23D—C24D0.5 (5)
C11B—C22B—C23B—C24B179.9 (3)C11D—C22D—C23D—C24D176.9 (3)
C22B—C23B—C24B—C25B0.2 (4)C22D—C23D—C24D—C25D0.2 (5)
C23B—C24B—C25B—C26B0.4 (5)C23D—C24D—C25D—C26D0.1 (5)
C24B—C25B—C26B—C27B0.1 (5)C24D—C25D—C26D—C27D0.8 (5)
C25B—C26B—C27B—C22B0.8 (5)C25D—C26D—C27D—C22D1.6 (5)
C23B—C22B—C27B—C26B0.9 (4)C23D—C22D—C27D—C26D1.4 (4)
C11B—C22B—C27B—C26B179.6 (3)C11D—C22D—C27D—C26D176.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O2C0.851.922.772 (4)175
O1W—H1W1···N6B0.852.102.944 (4)174
N7A—H1NA···N5Bi0.94 (5)2.15 (5)3.017 (4)153 (4)
N7A—H1NA···N6Bi0.94 (5)2.19 (6)3.016 (4)146 (3)
N2A—H2NA···O3A0.78 (3)2.35 (3)2.912 (3)130 (3)
N7B—H1NB···N6Aii0.86 (4)2.16 (4)2.964 (4)155 (3)
N3B—H2NB···O3B0.88 (3)2.25 (3)2.865 (3)127 (3)
N7C—H1NC···N6Diii0.80 (3)2.21 (3)2.990 (4)165 (3)
N3C—H2NC···O3C0.91 (3)2.21 (3)2.895 (3)132 (3)
N7D—H1ND···N6Ciii0.89 (3)2.25 (3)3.082 (4)157 (3)
N3D—H2ND···O3D0.94 (3)2.07 (3)2.841 (3)138 (3)
C1A—H1XA···O2Bi1.162.433.471 (10)148
C5A—H5AA···O4Aiv0.932.453.294 (4)151
C1B—H1BA···O4Bv0.932.403.278 (4)158
C11A—H11A···O4Aiv0.982.603.291 (4)128
C5B—H5BA···O2Aii0.932.513.405 (4)162
C19D—H19D···O2Bvi0.932.413.289 (11)157
C5D—H5DA···O4Diii0.932.473.328 (4)154
C23A—H23A···O3Aiv0.932.593.318 (4)136
C23B—H23B···O3Bv0.932.413.240 (4)149
C27C—H27C···O3Cvii0.932.523.359 (4)150
C27D—H27D···O3Diii0.932.423.258 (4)149
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x+2, y, z+1; (v) x, y+1, z+1; (vi) x, y, z1; (vii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC27H21N7O4S·0.06H2O
Mr540.69
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)15.6242 (19), 18.7430 (19), 18.9689 (19)
α, β, γ (°)111.235 (2), 93.970 (2), 101.636 (2)
V3)5009.4 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.64 × 0.08 × 0.07
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.893, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
54193, 17604, 12624
Rint0.057
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.141, 1.04
No. of reflections17604
No. of parameters1498
No. of restraints54
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.41, 0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O2C0.851.922.772 (4)175
O1W—H1W1···N6B0.852.102.944 (4)174
N7A—H1NA···N5Bi0.94 (5)2.15 (5)3.017 (4)153 (4)
N7A—H1NA···N6Bi0.94 (5)2.19 (6)3.016 (4)146 (3)
N2A—H2NA···O3A0.78 (3)2.35 (3)2.912 (3)130 (3)
N7B—H1NB···N6Aii0.86 (4)2.16 (4)2.964 (4)155 (3)
N3B—H2NB···O3B0.88 (3)2.25 (3)2.865 (3)127 (3)
N7C—H1NC···N6Diii0.80 (3)2.21 (3)2.990 (4)165 (3)
N3C—H2NC···O3C0.91 (3)2.21 (3)2.895 (3)132 (3)
N7D—H1ND···N6Ciii0.89 (3)2.25 (3)3.082 (4)157 (3)
N3D—H2ND···O3D0.94 (3)2.07 (3)2.841 (3)138 (3)
C1A—H1XA···O2Bi1.162.433.471 (10)148
C5A—H5AA···O4Aiv0.932.453.294 (4)151
C1B—H1BA···O4Bv0.932.403.278 (4)158
C11A—H11A···O4Aiv0.982.603.291 (4)128
C5B—H5BA···O2Aii0.932.513.405 (4)162
C19D—H19D···O2Bvi0.932.413.289 (11)157
C5D—H5DA···O4Diii0.932.473.328 (4)154
C23A—H23A···O3Aiv0.932.593.318 (4)136
C23B—H23B···O3Bv0.932.413.240 (4)149
C27C—H27C···O3Cvii0.932.523.359 (4)150
C27D—H27D···O3Diii0.932.423.258 (4)149
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x+2, y, z+1; (v) x, y+1, z+1; (vi) x, y, z1; (vii) x+1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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First citationWagner, H. & Hill, J. B. (1974). J. Med. Chem. 17, 1337–1338.  CrossRef CAS PubMed Web of Science Google Scholar

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