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ISSN: 2056-9890

7′-Phenyl-5′,6′,7′,7a′-tetra­hydro­dipiro[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 1 November 2011; accepted 2 November 2011; online 5 November 2011)

The asymmetric unit of the title compound, C28H21NO3S, contains two mol­ecules with similar geometries. The thia­zolidine rings adopt half-chair conformations while the pyrrolidine and the diketo-substituted five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. In one mol­ecule, the phenyl ring forms dihedral angles of 57.76 (12) and 71.79 (12)° with the fused benzene rings and the fused benzene rings form a dihedral angle of 57.75 (13)°. The corresponding dihedral angles in the other mol­ecule are 60.04 (12), 72.93 (12) and 54.51 (13)°. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol­ecules are linked via C—H⋯O and C—H⋯N hydrogen bonds into layers lying parallel to the ab plane.

Related literature

For related structures and background references, see: Wei et al. (2011a[Wei, A. C., Ali, M. A., Choon, T. S., Quah, C. K. & Fun, H.-K. (2011a). Acta Cryst. E67, o2383.],b[Wei, A. C., Ali, M. A., Ismail, R., Quah, C. K. & Fun, H.-K. (2011b). Acta Cryst. E67, o2381-o2382.],c[Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011c). Acta Cryst. E67, o2404.]); Kumar et al. (2010[Kumar, R. S., Osman, H., Ali, M. A., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o1540-o1541.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C28H21NO3S

  • Mr = 451.52

  • Monoclinic, P 2/c

  • a = 19.3315 (6) Å

  • b = 9.6523 (3) Å

  • c = 29.9731 (8) Å

  • β = 127.817 (2)°

  • V = 4418.1 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 100 K

  • 0.44 × 0.22 × 0.16 mm

Data collection
  • Bruker SMART 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 = 0.925, Tmax = 0.973

  • 47347 measured reflections

  • 12947 independent reflections

  • 7530 reflections with I > 2σ(I)

  • Rint = 0.067

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.155

  • S = 1.02

  • 12947 reflections

  • 595 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15A—H15A⋯O2Ai 0.95 2.51 3.235 (3) 134
C16B—H16B⋯N1Bii 0.95 2.48 3.383 (3) 159
C18B—H18B⋯O2B 0.99 2.33 3.070 (4) 131
C18A—H18C⋯O2A 0.99 2.40 3.167 (4) 133
C19A—H19A⋯O1A 1.00 2.37 3.075 (4) 127
C19B—H19B⋯O1B 1.00 2.40 3.086 (4) 125
C23A—H23A⋯O1Biii 0.95 2.50 3.209 (4) 132
C23B—H23B⋯O1A 0.95 2.58 3.227 (4) 126
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+2, -y, -z+2; (iii) 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

As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei et al., 2011a,b,c), our group has synthesized the title compound as described below.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. The thiazolidine (S1/N1/C26-C28) rings are twisted about S1-C27 bonds, with puckering parameters (Cremer & Pople,1975) Q = 0.423 (2) Å and φ = 22.4 (3)°; and Q = 0.443 (2) Å and φ = 203.1 (3)°, in molecules A and B, respectively, thereby adopting a half-chair conformation. The pyrrolidine (N1/C9/C10/C19/C27, puckering parameters Q = 0.489 (3) Å and φ = 245.0 (3)° with atom C10A at the flap; and Q = 0.485 (3) Å and φ = 65.8 (3)° with atom C10B at the flap, in molecules A and B, respectively) and five-membered carbocyclic (C1/C2/C7-C9, puckering parameters Q = 0.176 (3) Å and φ = 138.9 (9)° with atom C9A at the flap; and Q = 0.153 (3) Å and φ = 319.9 (10)° with atom C9B at the flap, in molecules A and B, respectively) rings are in envelope conformations. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Kumar et al., 2010; Wei et al., 2011a,b,c). In molecule A, the phenyl (C20A-C25A) ring forms dihedral angles of 57.76 (12) and 71.79 (12)° with the two benzene (C2A-C7A and C12A-C17A) rings, respectively and the two benzene rings form a dihedral angle of 57.75 (13)°. The corresponding dihedral angles in molecule B are 60.04 (12), 72.93 (12) and 54.51 (13)°. The molecular structure is stabilized by intramolecular C18A–H18C···O2A, C18B–H18B···O2B, C19A–H19A···O1A and C19B–H19B···O1B hydrogen bonds (Table 1), which generate S(6) ring motifs (Fig. 1, Bernstein et al., 1995).

In the crystal, Fig. 2, molecules are linked via intermolecular C15A–H15A···O2A, C16B–H16B···N1B, C23A–H23A···O1B and C23B–H23B···O1A hydrogen bonds (Table 1) into two-dimensional layers parallel to the ab-plane.

Related literature top

For related structures and background references, see: Wei et al. (2011a,b,c); Kumar et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of (Z)-(2-benzylidene)-2,3-dihydro-1H-indene-1-one (0.001 mol), ninhydrin (0.001 mol) and thiazolidine-4-carboxylic acid (0.002 mol) (1:1:2) was dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice. The precipitated solid was filtered, washed and recrystallized from a petroleum ether–ethyl acetate mixture (1:1) to afford the title compound as yellow blocks.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C–H = 0.95-1.00 Å and Uiso(H) = 1.2 Ueq(C).

Structure description top

As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei et al., 2011a,b,c), our group has synthesized the title compound as described below.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. The thiazolidine (S1/N1/C26-C28) rings are twisted about S1-C27 bonds, with puckering parameters (Cremer & Pople,1975) Q = 0.423 (2) Å and φ = 22.4 (3)°; and Q = 0.443 (2) Å and φ = 203.1 (3)°, in molecules A and B, respectively, thereby adopting a half-chair conformation. The pyrrolidine (N1/C9/C10/C19/C27, puckering parameters Q = 0.489 (3) Å and φ = 245.0 (3)° with atom C10A at the flap; and Q = 0.485 (3) Å and φ = 65.8 (3)° with atom C10B at the flap, in molecules A and B, respectively) and five-membered carbocyclic (C1/C2/C7-C9, puckering parameters Q = 0.176 (3) Å and φ = 138.9 (9)° with atom C9A at the flap; and Q = 0.153 (3) Å and φ = 319.9 (10)° with atom C9B at the flap, in molecules A and B, respectively) rings are in envelope conformations. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Kumar et al., 2010; Wei et al., 2011a,b,c). In molecule A, the phenyl (C20A-C25A) ring forms dihedral angles of 57.76 (12) and 71.79 (12)° with the two benzene (C2A-C7A and C12A-C17A) rings, respectively and the two benzene rings form a dihedral angle of 57.75 (13)°. The corresponding dihedral angles in molecule B are 60.04 (12), 72.93 (12) and 54.51 (13)°. The molecular structure is stabilized by intramolecular C18A–H18C···O2A, C18B–H18B···O2B, C19A–H19A···O1A and C19B–H19B···O1B hydrogen bonds (Table 1), which generate S(6) ring motifs (Fig. 1, Bernstein et al., 1995).

In the crystal, Fig. 2, molecules are linked via intermolecular C15A–H15A···O2A, C16B–H16B···N1B, C23A–H23A···O1B and C23B–H23B···O1A hydrogen bonds (Table 1) into two-dimensional layers parallel to the ab-plane.

For related structures and background references, see: Wei et al. (2011a,b,c); Kumar et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

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. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
7'-Phenyl-5',6',7',7a'-tetrahydrodipiro[indan-2,5'- pyrrolo[1,2-c][1,3]thiazole-6',2''-indan]-1,3,1''-trione top
Crystal data top
C28H21NO3SF(000) = 1888
Mr = 451.52Dx = 1.358 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 8142 reflections
a = 19.3315 (6) Åθ = 2.3–29.7°
b = 9.6523 (3) ŵ = 0.18 mm1
c = 29.9731 (8) ÅT = 100 K
β = 127.817 (2)°Block, yellow
V = 4418.1 (2) Å30.44 × 0.22 × 0.16 mm
Z = 8
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
12947 independent reflections
Radiation source: fine-focus sealed tube7530 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
φ and ω scansθmax = 30.1°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2727
Tmin = 0.925, Tmax = 0.973k = 1313
47347 measured reflectionsl = 4142
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0595P)2 + 1.4465P]
where P = (Fo2 + 2Fc2)/3
12947 reflections(Δ/σ)max = 0.001
595 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
C28H21NO3SV = 4418.1 (2) Å3
Mr = 451.52Z = 8
Monoclinic, P2/cMo Kα radiation
a = 19.3315 (6) ŵ = 0.18 mm1
b = 9.6523 (3) ÅT = 100 K
c = 29.9731 (8) Å0.44 × 0.22 × 0.16 mm
β = 127.817 (2)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
12947 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
7530 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.973Rint = 0.067
47347 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.02Δρmax = 0.45 e Å3
12947 reflectionsΔρmin = 0.49 e Å3
595 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/Ueq
S1A0.62967 (4)0.26781 (6)0.97231 (3)0.02670 (15)
O1A0.53829 (10)0.50566 (16)0.83979 (6)0.0202 (3)
O2A0.65120 (10)0.80602 (18)0.99202 (6)0.0279 (4)
O3A0.39540 (10)0.75090 (15)0.79654 (6)0.0202 (3)
N1A0.57530 (11)0.52837 (18)0.95265 (7)0.0171 (4)
C1A0.55815 (13)0.6143 (2)0.86534 (8)0.0168 (5)
C2A0.59616 (14)0.7378 (2)0.85871 (9)0.0174 (5)
C3A0.60336 (14)0.7671 (2)0.81616 (9)0.0222 (5)
H3AA0.58270.70420.78600.027*
C4A0.64194 (15)0.8918 (3)0.81962 (10)0.0272 (6)
H4AA0.64670.91580.79090.033*
C5A0.67402 (16)0.9831 (3)0.86471 (10)0.0284 (6)
H5AA0.70021.06780.86590.034*
C6A0.66852 (15)0.9527 (2)0.90770 (10)0.0253 (5)
H6AA0.69141.01410.93860.030*
C7A0.62811 (14)0.8285 (2)0.90376 (9)0.0205 (5)
C8A0.61574 (14)0.7684 (2)0.94378 (9)0.0195 (5)
C9A0.55364 (14)0.6436 (2)0.91497 (8)0.0166 (4)
C10A0.45760 (14)0.6739 (2)0.89214 (8)0.0167 (5)
C11A0.40732 (14)0.7725 (2)0.84090 (9)0.0166 (4)
C12A0.37781 (13)0.8917 (2)0.85542 (8)0.0155 (4)
C13A0.32921 (14)1.0064 (2)0.82197 (9)0.0186 (5)
H13A0.31201.01580.78490.022*
C14A0.30687 (15)1.1057 (2)0.84438 (9)0.0217 (5)
H14A0.27371.18430.82250.026*
C15A0.33283 (15)1.0909 (2)0.89928 (9)0.0210 (5)
H15A0.31691.15990.91410.025*
C16A0.38156 (14)0.9771 (2)0.93249 (9)0.0189 (5)
H16A0.39920.96820.96970.023*
C17A0.40395 (14)0.8766 (2)0.91014 (8)0.0164 (4)
C18A0.45288 (14)0.7428 (2)0.93681 (9)0.0175 (5)
H18A0.42120.68270.94560.021*
H18C0.51240.76110.97210.021*
C19A0.42138 (13)0.5225 (2)0.87689 (8)0.0157 (4)
H19A0.42040.49410.84440.019*
C20A0.32991 (14)0.4993 (2)0.85811 (9)0.0163 (4)
C21A0.30942 (14)0.4529 (2)0.89297 (9)0.0189 (5)
H21A0.35470.44090.93230.023*
C22A0.22318 (15)0.4240 (2)0.87041 (9)0.0219 (5)
H22A0.21050.39060.89450.026*
C23A0.15545 (15)0.4430 (2)0.81357 (9)0.0227 (5)
H23A0.09680.42190.79860.027*
C24A0.17451 (15)0.4935 (2)0.77879 (10)0.0252 (5)
H24A0.12860.50980.73990.030*
C25A0.26034 (14)0.5199 (2)0.80094 (9)0.0200 (5)
H25A0.27250.55320.77660.024*
C26A0.49677 (14)0.4401 (2)0.92853 (9)0.0183 (5)
H26A0.48530.43050.95670.022*
C27A0.51469 (14)0.2975 (2)0.91563 (10)0.0239 (5)
H27A0.50300.29720.87850.029*
H27C0.47800.22590.91550.029*
C28A0.65485 (14)0.4502 (2)0.97413 (9)0.0203 (5)
H28A0.70290.47901.01330.024*
H28C0.67340.46700.95030.024*
S1B1.12519 (4)0.51070 (6)0.97238 (3)0.02524 (15)
O1B1.03573 (10)0.27798 (16)0.83636 (6)0.0218 (3)
O2B1.12668 (10)0.03342 (16)0.98297 (6)0.0242 (4)
O3B0.88255 (10)0.04463 (16)0.78666 (6)0.0211 (3)
N1B1.06431 (11)0.25445 (18)0.94627 (7)0.0169 (4)
C1B1.05240 (13)0.1689 (2)0.86112 (9)0.0173 (5)
C2B1.09053 (14)0.0444 (2)0.85552 (9)0.0181 (5)
C3B1.10378 (14)0.0155 (2)0.81586 (9)0.0221 (5)
H3BA1.08690.07960.78670.027*
C4B1.14246 (15)0.1098 (3)0.82023 (10)0.0266 (5)
H4BA1.15150.13260.79330.032*
C5B1.16840 (16)0.2033 (3)0.86366 (10)0.0295 (6)
H5BA1.19500.28840.86580.035*
C6B1.15601 (15)0.1742 (2)0.90362 (10)0.0241 (5)
H6BA1.17380.23770.93310.029*
C7B1.11677 (14)0.0489 (2)0.89915 (9)0.0193 (5)
C8B1.09942 (14)0.0095 (2)0.93695 (9)0.0191 (5)
C9B1.04226 (14)0.1407 (2)0.90805 (8)0.0165 (4)
C10B0.94408 (14)0.1170 (2)0.88260 (8)0.0166 (4)
C11B0.89434 (14)0.0205 (2)0.83098 (8)0.0163 (4)
C12B0.86614 (14)0.1020 (2)0.84504 (9)0.0164 (4)
C13B0.82083 (14)0.2189 (2)0.81213 (9)0.0190 (5)
H13B0.80370.22720.77500.023*
C14B0.80152 (15)0.3220 (2)0.83486 (9)0.0218 (5)
H14B0.77020.40190.81310.026*
C15B0.82820 (15)0.3090 (2)0.89015 (9)0.0211 (5)
H15B0.81550.38140.90560.025*
C16B0.87255 (14)0.1927 (2)0.92241 (9)0.0195 (5)
H16B0.88990.18460.95960.023*
C17B0.89134 (13)0.0879 (2)0.89954 (8)0.0157 (4)
C18B0.93578 (14)0.0482 (2)0.92581 (9)0.0177 (5)
H18B0.99420.03370.96240.021*
H18D0.90020.10640.93210.021*
C19B0.91199 (13)0.2697 (2)0.86880 (8)0.0164 (4)
H19B0.91290.29940.83720.020*
C20B0.81980 (14)0.2937 (2)0.84906 (9)0.0166 (4)
C21B0.79908 (15)0.3294 (2)0.88491 (9)0.0200 (5)
H21B0.84430.33710.92440.024*
C22B0.71272 (15)0.3535 (2)0.86304 (10)0.0250 (5)
H22B0.69970.37850.88780.030*
C23B0.64529 (15)0.3417 (2)0.80574 (10)0.0263 (5)
H23B0.58650.35970.79100.032*
C24B0.66510 (15)0.3031 (2)0.77019 (10)0.0260 (5)
H24B0.61930.29200.73090.031*
C25B0.75119 (14)0.2807 (2)0.79155 (9)0.0202 (5)
H25B0.76370.25590.76650.024*
C26B0.98754 (13)0.3470 (2)0.92214 (9)0.0180 (5)
H26B0.97430.35610.94940.022*
C27B1.01105 (14)0.4886 (2)0.91226 (9)0.0228 (5)
H27B0.97440.56230.91120.027*
H27D1.00340.49000.87640.027*
C28B1.14705 (14)0.3275 (2)0.97163 (9)0.0210 (5)
H28D1.16810.31220.94910.025*
H28E1.19230.29381.01050.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0213 (3)0.0209 (3)0.0327 (3)0.0081 (2)0.0139 (3)0.0062 (3)
O1A0.0215 (8)0.0199 (9)0.0223 (8)0.0007 (7)0.0150 (7)0.0036 (7)
O2A0.0270 (9)0.0345 (10)0.0219 (8)0.0055 (8)0.0148 (7)0.0085 (7)
O3A0.0248 (9)0.0214 (9)0.0183 (7)0.0026 (7)0.0152 (7)0.0017 (6)
N1A0.0166 (10)0.0172 (10)0.0187 (9)0.0026 (8)0.0114 (8)0.0021 (7)
C1A0.0129 (11)0.0209 (12)0.0173 (10)0.0054 (9)0.0096 (9)0.0026 (9)
C2A0.0136 (11)0.0193 (12)0.0191 (10)0.0021 (9)0.0099 (9)0.0006 (9)
C3A0.0194 (12)0.0271 (13)0.0215 (11)0.0014 (10)0.0134 (10)0.0000 (10)
C4A0.0254 (13)0.0310 (15)0.0312 (13)0.0008 (11)0.0205 (11)0.0059 (11)
C5A0.0263 (14)0.0220 (13)0.0391 (14)0.0029 (11)0.0212 (12)0.0019 (11)
C6A0.0215 (13)0.0205 (13)0.0315 (13)0.0014 (10)0.0151 (11)0.0030 (10)
C7A0.0155 (12)0.0216 (12)0.0219 (11)0.0014 (9)0.0102 (9)0.0019 (9)
C8A0.0169 (11)0.0215 (12)0.0198 (11)0.0020 (9)0.0111 (9)0.0026 (9)
C9A0.0165 (11)0.0189 (11)0.0161 (10)0.0035 (9)0.0109 (9)0.0016 (9)
C10A0.0187 (11)0.0170 (11)0.0179 (10)0.0027 (9)0.0129 (9)0.0010 (9)
C11A0.0159 (11)0.0166 (11)0.0193 (10)0.0013 (9)0.0117 (9)0.0013 (9)
C12A0.0137 (11)0.0146 (11)0.0175 (10)0.0002 (8)0.0093 (9)0.0012 (8)
C13A0.0204 (12)0.0165 (11)0.0186 (10)0.0005 (9)0.0119 (9)0.0018 (9)
C14A0.0246 (13)0.0162 (12)0.0211 (11)0.0045 (10)0.0125 (10)0.0050 (9)
C15A0.0249 (12)0.0161 (12)0.0241 (11)0.0010 (10)0.0161 (10)0.0011 (9)
C16A0.0230 (12)0.0175 (12)0.0188 (10)0.0004 (9)0.0141 (10)0.0006 (9)
C17A0.0155 (11)0.0158 (11)0.0183 (10)0.0011 (9)0.0105 (9)0.0002 (9)
C18A0.0201 (11)0.0171 (11)0.0189 (10)0.0040 (9)0.0138 (9)0.0041 (9)
C19A0.0172 (11)0.0155 (11)0.0168 (10)0.0031 (9)0.0116 (9)0.0019 (8)
C20A0.0171 (11)0.0123 (11)0.0218 (10)0.0019 (9)0.0132 (9)0.0001 (9)
C21A0.0206 (12)0.0177 (12)0.0190 (10)0.0028 (9)0.0125 (9)0.0010 (9)
C22A0.0277 (13)0.0182 (12)0.0303 (12)0.0000 (10)0.0232 (11)0.0028 (10)
C23A0.0177 (12)0.0217 (13)0.0295 (12)0.0024 (10)0.0150 (10)0.0006 (10)
C24A0.0200 (13)0.0280 (14)0.0232 (11)0.0017 (10)0.0110 (10)0.0032 (10)
C25A0.0220 (12)0.0194 (12)0.0197 (11)0.0015 (9)0.0133 (9)0.0031 (9)
C26A0.0184 (12)0.0178 (12)0.0202 (10)0.0044 (9)0.0125 (9)0.0041 (9)
C27A0.0201 (12)0.0173 (12)0.0304 (12)0.0042 (10)0.0135 (10)0.0038 (10)
C28A0.0165 (11)0.0225 (12)0.0214 (11)0.0058 (9)0.0113 (9)0.0031 (9)
S1B0.0198 (3)0.0196 (3)0.0297 (3)0.0061 (2)0.0118 (3)0.0037 (2)
O1B0.0233 (9)0.0207 (9)0.0262 (8)0.0016 (7)0.0177 (7)0.0044 (7)
O2B0.0241 (9)0.0251 (9)0.0193 (8)0.0018 (7)0.0112 (7)0.0062 (7)
O3B0.0240 (9)0.0231 (9)0.0179 (8)0.0024 (7)0.0136 (7)0.0008 (6)
N1B0.0149 (9)0.0175 (10)0.0179 (9)0.0032 (7)0.0097 (8)0.0023 (7)
C1B0.0128 (11)0.0218 (12)0.0168 (10)0.0021 (9)0.0088 (9)0.0004 (9)
C2B0.0136 (11)0.0210 (12)0.0169 (10)0.0014 (9)0.0080 (9)0.0004 (9)
C3B0.0190 (12)0.0268 (13)0.0229 (11)0.0003 (10)0.0140 (10)0.0003 (10)
C4B0.0263 (13)0.0292 (14)0.0283 (12)0.0008 (11)0.0188 (11)0.0059 (11)
C5B0.0301 (14)0.0231 (13)0.0373 (14)0.0034 (11)0.0217 (12)0.0024 (11)
C6B0.0225 (13)0.0191 (13)0.0277 (12)0.0017 (10)0.0139 (10)0.0015 (10)
C7B0.0134 (11)0.0198 (12)0.0207 (11)0.0012 (9)0.0085 (9)0.0005 (9)
C8B0.0153 (11)0.0191 (12)0.0186 (10)0.0047 (9)0.0082 (9)0.0024 (9)
C9B0.0159 (11)0.0177 (11)0.0175 (10)0.0013 (9)0.0111 (9)0.0008 (9)
C10B0.0175 (11)0.0166 (11)0.0178 (10)0.0041 (9)0.0119 (9)0.0035 (9)
C11B0.0160 (11)0.0174 (11)0.0176 (10)0.0008 (9)0.0115 (9)0.0006 (9)
C12B0.0157 (11)0.0143 (11)0.0195 (10)0.0013 (9)0.0109 (9)0.0009 (9)
C13B0.0199 (12)0.0179 (12)0.0173 (10)0.0000 (9)0.0105 (9)0.0020 (9)
C14B0.0249 (13)0.0152 (12)0.0235 (11)0.0041 (10)0.0140 (10)0.0043 (9)
C15B0.0255 (13)0.0164 (12)0.0230 (11)0.0028 (10)0.0157 (10)0.0022 (9)
C16B0.0220 (12)0.0179 (12)0.0203 (11)0.0030 (9)0.0138 (10)0.0021 (9)
C17B0.0136 (11)0.0145 (11)0.0185 (10)0.0004 (8)0.0097 (9)0.0011 (8)
C18B0.0189 (12)0.0195 (12)0.0176 (10)0.0037 (9)0.0125 (9)0.0018 (9)
C19B0.0181 (11)0.0143 (11)0.0182 (10)0.0031 (9)0.0119 (9)0.0028 (8)
C20B0.0171 (11)0.0118 (11)0.0234 (11)0.0037 (9)0.0136 (9)0.0019 (9)
C21B0.0215 (12)0.0183 (12)0.0220 (11)0.0021 (9)0.0143 (10)0.0037 (9)
C22B0.0271 (14)0.0217 (13)0.0338 (13)0.0030 (10)0.0225 (11)0.0080 (10)
C23B0.0167 (12)0.0243 (13)0.0352 (13)0.0001 (10)0.0145 (11)0.0039 (11)
C24B0.0212 (13)0.0246 (13)0.0251 (12)0.0021 (10)0.0106 (10)0.0029 (10)
C25B0.0208 (12)0.0199 (12)0.0218 (11)0.0008 (9)0.0141 (10)0.0027 (9)
C26B0.0158 (11)0.0188 (12)0.0203 (10)0.0018 (9)0.0116 (9)0.0012 (9)
C27B0.0180 (12)0.0186 (12)0.0276 (12)0.0033 (9)0.0118 (10)0.0026 (10)
C28B0.0186 (12)0.0219 (13)0.0229 (11)0.0033 (10)0.0129 (10)0.0003 (9)
Geometric parameters (Å, º) top
S1A—C27A1.811 (2)S1B—C27B1.813 (2)
S1A—C28A1.818 (2)S1B—C28B1.822 (2)
O1A—C1A1.214 (2)O1B—C1B1.212 (2)
O2A—C8A1.215 (2)O2B—C8B1.209 (2)
O3A—C11A1.220 (2)O3B—C11B1.225 (2)
N1A—C9A1.452 (3)N1B—C9B1.449 (3)
N1A—C28A1.461 (3)N1B—C28B1.463 (3)
N1A—C26A1.485 (3)N1B—C26B1.486 (3)
C1A—C2A1.476 (3)C1B—C2B1.472 (3)
C1A—C9A1.568 (3)C1B—C9B1.559 (3)
C2A—C3A1.394 (3)C2B—C3B1.389 (3)
C2A—C7A1.396 (3)C2B—C7B1.402 (3)
C3A—C4A1.386 (3)C3B—C4B1.385 (3)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.400 (3)C4B—C5B1.400 (3)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.388 (3)C5B—C6B1.387 (3)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.396 (3)C6B—C7B1.389 (3)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.478 (3)C7B—C8B1.477 (3)
C8A—C9A1.539 (3)C8B—C9B1.550 (3)
C9A—C10A1.563 (3)C9B—C10B1.569 (3)
C10A—C11A1.542 (3)C10B—C11B1.537 (3)
C10A—C18A1.547 (3)C10B—C18B1.549 (3)
C10A—C19A1.563 (3)C10B—C19B1.554 (3)
C11A—C12A1.464 (3)C11B—C12B1.468 (3)
C12A—C17A1.396 (3)C12B—C17B1.396 (3)
C12A—C13A1.400 (3)C12B—C13B1.398 (3)
C13A—C14A1.382 (3)C13B—C14B1.380 (3)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.402 (3)C14B—C15B1.407 (3)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.391 (3)C15B—C16B1.383 (3)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.390 (3)C16B—C17B1.390 (3)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.508 (3)C17B—C18B1.501 (3)
C18A—H18A0.9900C18B—H18B0.9900
C18A—H18C0.9900C18B—H18D0.9900
C19A—C20A1.508 (3)C19B—C20B1.512 (3)
C19A—C26A1.544 (3)C19B—C26B1.543 (3)
C19A—H19A1.0000C19B—H19B1.0000
C20A—C21A1.399 (3)C20B—C25B1.394 (3)
C20A—C25A1.399 (3)C20B—C21B1.400 (3)
C21A—C22A1.390 (3)C21B—C22B1.389 (3)
C21A—H21A0.9500C21B—H21B0.9500
C22A—C23A1.384 (3)C22B—C23B1.384 (3)
C22A—H22A0.9500C22B—H22B0.9500
C23A—C24A1.389 (3)C23B—C24B1.386 (3)
C23A—H23A0.9500C23B—H23B0.9500
C24A—C25A1.381 (3)C24B—C25B1.386 (3)
C24A—H24A0.9500C24B—H24B0.9500
C25A—H25A0.9500C25B—H25B0.9500
C26A—C27A1.526 (3)C26B—C27B1.526 (3)
C26A—H26A1.0000C26B—H26B1.0000
C27A—H27A0.9900C27B—H27B0.9900
C27A—H27C0.9900C27B—H27D0.9900
C28A—H28A0.9900C28B—H28D0.9900
C28A—H28C0.9900C28B—H28E0.9900
C27A—S1A—C28A91.53 (10)C27B—S1B—C28B91.36 (10)
C9A—N1A—C28A117.51 (17)C9B—N1B—C28B118.27 (17)
C9A—N1A—C26A109.83 (16)C9B—N1B—C26B110.40 (16)
C28A—N1A—C26A113.82 (17)C28B—N1B—C26B114.26 (17)
O1A—C1A—C2A127.13 (19)O1B—C1B—C2B127.08 (19)
O1A—C1A—C9A125.02 (19)O1B—C1B—C9B124.77 (19)
C2A—C1A—C9A107.72 (18)C2B—C1B—C9B108.03 (18)
C3A—C2A—C7A121.6 (2)C3B—C2B—C7B121.2 (2)
C3A—C2A—C1A128.6 (2)C3B—C2B—C1B129.0 (2)
C7A—C2A—C1A109.73 (18)C7B—C2B—C1B109.78 (18)
C4A—C3A—C2A117.3 (2)C4B—C3B—C2B117.8 (2)
C4A—C3A—H3AA121.3C4B—C3B—H3BA121.1
C2A—C3A—H3AA121.3C2B—C3B—H3BA121.1
C3A—C4A—C5A121.2 (2)C3B—C4B—C5B121.1 (2)
C3A—C4A—H4AA119.4C3B—C4B—H4BA119.5
C5A—C4A—H4AA119.4C5B—C4B—H4BA119.5
C6A—C5A—C4A121.5 (2)C6B—C5B—C4B121.3 (2)
C6A—C5A—H5AA119.2C6B—C5B—H5BA119.4
C4A—C5A—H5AA119.2C4B—C5B—H5BA119.4
C5A—C6A—C7A117.4 (2)C5B—C6B—C7B117.8 (2)
C5A—C6A—H6AA121.3C5B—C6B—H6BA121.1
C7A—C6A—H6AA121.3C7B—C6B—H6BA121.1
C6A—C7A—C2A120.9 (2)C6B—C7B—C2B120.9 (2)
C6A—C7A—C8A129.0 (2)C6B—C7B—C8B128.7 (2)
C2A—C7A—C8A110.06 (19)C2B—C7B—C8B110.34 (19)
O2A—C8A—C7A126.4 (2)O2B—C8B—C7B126.8 (2)
O2A—C8A—C9A125.4 (2)O2B—C8B—C9B125.5 (2)
C7A—C8A—C9A108.11 (17)C7B—C8B—C9B107.63 (17)
N1A—C9A—C8A114.17 (17)N1B—C9B—C8B114.46 (17)
N1A—C9A—C10A100.53 (16)N1B—C9B—C1B116.27 (17)
C8A—C9A—C10A114.04 (17)C8B—C9B—C1B101.87 (17)
N1A—C9A—C1A116.30 (17)N1B—C9B—C10B100.19 (16)
C8A—C9A—C1A101.25 (17)C8B—C9B—C10B112.82 (17)
C10A—C9A—C1A111.14 (16)C1B—C9B—C10B111.76 (16)
C11A—C10A—C18A105.14 (17)C11B—C10B—C18B105.07 (17)
C11A—C10A—C9A113.93 (17)C11B—C10B—C19B113.95 (17)
C18A—C10A—C9A112.73 (17)C18B—C10B—C19B113.60 (17)
C11A—C10A—C19A112.94 (17)C11B—C10B—C9B113.69 (17)
C18A—C10A—C19A113.69 (17)C18B—C10B—C9B111.76 (17)
C9A—C10A—C19A98.71 (16)C19B—C10B—C9B99.06 (16)
O3A—C11A—C12A127.63 (19)O3B—C11B—C12B127.59 (19)
O3A—C11A—C10A124.24 (19)O3B—C11B—C10B124.19 (19)
C12A—C11A—C10A108.13 (17)C12B—C11B—C10B108.22 (17)
C17A—C12A—C13A121.60 (19)C17B—C12B—C13B121.5 (2)
C17A—C12A—C11A109.95 (18)C17B—C12B—C11B109.41 (18)
C13A—C12A—C11A128.44 (19)C13B—C12B—C11B129.05 (19)
C14A—C13A—C12A118.22 (19)C14B—C13B—C12B118.40 (19)
C14A—C13A—H13A120.9C14B—C13B—H13B120.8
C12A—C13A—H13A120.9C12B—C13B—H13B120.8
C13A—C14A—C15A120.4 (2)C13B—C14B—C15B120.1 (2)
C13A—C14A—H14A119.8C13B—C14B—H14B119.9
C15A—C14A—H14A119.8C15B—C14B—H14B119.9
C16A—C15A—C14A121.2 (2)C16B—C15B—C14B121.2 (2)
C16A—C15A—H15A119.4C16B—C15B—H15B119.4
C14A—C15A—H15A119.4C14B—C15B—H15B119.4
C17A—C16A—C15A118.72 (19)C15B—C16B—C17B118.9 (2)
C17A—C16A—H16A120.6C15B—C16B—H16B120.5
C15A—C16A—H16A120.6C17B—C16B—H16B120.5
C16A—C17A—C12A119.87 (19)C16B—C17B—C12B119.8 (2)
C16A—C17A—C18A128.43 (19)C16B—C17B—C18B128.11 (19)
C12A—C17A—C18A111.67 (18)C12B—C17B—C18B112.11 (18)
C17A—C18A—C10A105.08 (16)C17B—C18B—C10B104.84 (16)
C17A—C18A—H18A110.7C17B—C18B—H18B110.8
C10A—C18A—H18A110.7C10B—C18B—H18B110.8
C17A—C18A—H18C110.7C17B—C18B—H18D110.8
C10A—C18A—H18C110.7C10B—C18B—H18D110.8
H18A—C18A—H18C108.8H18B—C18B—H18D108.9
C20A—C19A—C26A117.91 (17)C20B—C19B—C26B118.09 (17)
C20A—C19A—C10A117.38 (17)C20B—C19B—C10B115.59 (17)
C26A—C19A—C10A102.11 (16)C26B—C19B—C10B102.28 (16)
C20A—C19A—H19A106.2C20B—C19B—H19B106.7
C26A—C19A—H19A106.2C26B—C19B—H19B106.7
C10A—C19A—H19A106.2C10B—C19B—H19B106.7
C21A—C20A—C25A117.4 (2)C25B—C20B—C21B117.9 (2)
C21A—C20A—C19A124.95 (19)C25B—C20B—C19B118.00 (19)
C25A—C20A—C19A117.56 (19)C21B—C20B—C19B124.09 (19)
C22A—C21A—C20A120.3 (2)C22B—C21B—C20B120.4 (2)
C22A—C21A—H21A119.8C22B—C21B—H21B119.8
C20A—C21A—H21A119.8C20B—C21B—H21B119.8
C23A—C22A—C21A121.3 (2)C23B—C22B—C21B121.1 (2)
C23A—C22A—H22A119.3C23B—C22B—H22B119.4
C21A—C22A—H22A119.3C21B—C22B—H22B119.4
C22A—C23A—C24A119.0 (2)C22B—C23B—C24B118.8 (2)
C22A—C23A—H23A120.5C22B—C23B—H23B120.6
C24A—C23A—H23A120.5C24B—C23B—H23B120.6
C25A—C24A—C23A119.8 (2)C25B—C24B—C23B120.4 (2)
C25A—C24A—H24A120.1C25B—C24B—H24B119.8
C23A—C24A—H24A120.1C23B—C24B—H24B119.8
C24A—C25A—C20A122.1 (2)C24B—C25B—C20B121.3 (2)
C24A—C25A—H25A118.9C24B—C25B—H25B119.3
C20A—C25A—H25A118.9C20B—C25B—H25B119.3
N1A—C26A—C27A108.50 (17)N1B—C26B—C27B107.79 (17)
N1A—C26A—C19A104.34 (16)N1B—C26B—C19B104.02 (16)
C27A—C26A—C19A115.54 (18)C27B—C26B—C19B115.93 (17)
N1A—C26A—H26A109.4N1B—C26B—H26B109.6
C27A—C26A—H26A109.4C27B—C26B—H26B109.6
C19A—C26A—H26A109.4C19B—C26B—H26B109.6
C26A—C27A—S1A104.12 (15)C26B—C27B—S1B103.79 (15)
C26A—C27A—H27A110.9C26B—C27B—H27B111.0
S1A—C27A—H27A110.9S1B—C27B—H27B111.0
C26A—C27A—H27C110.9C26B—C27B—H27D111.0
S1A—C27A—H27C110.9S1B—C27B—H27D111.0
H27A—C27A—H27C109.0H27B—C27B—H27D109.0
N1A—C28A—S1A107.26 (15)N1B—C28B—S1B106.62 (15)
N1A—C28A—H28A110.3N1B—C28B—H28D110.4
S1A—C28A—H28A110.3S1B—C28B—H28D110.4
N1A—C28A—H28C110.3N1B—C28B—H28E110.4
S1A—C28A—H28C110.3S1B—C28B—H28E110.4
H28A—C28A—H28C108.5H28D—C28B—H28E108.6
O1A—C1A—C2A—C3A12.4 (4)O1B—C1B—C2B—C3B10.6 (4)
C9A—C1A—C2A—C3A171.6 (2)C9B—C1B—C2B—C3B173.2 (2)
O1A—C1A—C2A—C7A166.5 (2)O1B—C1B—C2B—C7B167.6 (2)
C9A—C1A—C2A—C7A9.6 (2)C9B—C1B—C2B—C7B8.6 (2)
C7A—C2A—C3A—C4A1.4 (3)C7B—C2B—C3B—C4B1.1 (3)
C1A—C2A—C3A—C4A179.8 (2)C1B—C2B—C3B—C4B179.1 (2)
C2A—C3A—C4A—C5A1.3 (3)C2B—C3B—C4B—C5B0.8 (3)
C3A—C4A—C5A—C6A0.0 (4)C3B—C4B—C5B—C6B0.3 (4)
C4A—C5A—C6A—C7A1.2 (3)C4B—C5B—C6B—C7B0.1 (4)
C5A—C6A—C7A—C2A1.2 (3)C5B—C6B—C7B—C2B0.1 (3)
C5A—C6A—C7A—C8A177.9 (2)C5B—C6B—C7B—C8B177.3 (2)
C3A—C2A—C7A—C6A0.1 (3)C3B—C2B—C7B—C6B0.7 (3)
C1A—C2A—C7A—C6A179.1 (2)C1B—C2B—C7B—C6B179.1 (2)
C3A—C2A—C7A—C8A177.2 (2)C3B—C2B—C7B—C8B177.1 (2)
C1A—C2A—C7A—C8A1.8 (2)C1B—C2B—C7B—C8B1.3 (2)
C6A—C7A—C8A—O2A12.8 (4)C6B—C7B—C8B—O2B10.5 (4)
C2A—C7A—C8A—O2A164.2 (2)C2B—C7B—C8B—O2B167.1 (2)
C6A—C7A—C8A—C9A170.3 (2)C6B—C7B—C8B—C9B171.7 (2)
C2A—C7A—C8A—C9A12.7 (2)C2B—C7B—C8B—C9B10.7 (2)
C28A—N1A—C9A—C8A69.7 (2)C28B—N1B—C9B—C8B70.3 (2)
C26A—N1A—C9A—C8A158.05 (17)C26B—N1B—C9B—C8B155.47 (17)
C28A—N1A—C9A—C10A167.74 (17)C28B—N1B—C9B—C1B48.2 (2)
C26A—N1A—C9A—C10A35.5 (2)C26B—N1B—C9B—C1B86.1 (2)
C28A—N1A—C9A—C1A47.7 (3)C28B—N1B—C9B—C10B168.74 (17)
C26A—N1A—C9A—C1A84.5 (2)C26B—N1B—C9B—C10B34.5 (2)
O2A—C8A—C9A—N1A34.0 (3)O2B—C8B—C9B—N1B36.7 (3)
C7A—C8A—C9A—N1A142.94 (18)C7B—C8B—C9B—N1B141.11 (18)
O2A—C8A—C9A—C10A80.8 (3)O2B—C8B—C9B—C1B163.1 (2)
C7A—C8A—C9A—C10A102.3 (2)C7B—C8B—C9B—C1B14.8 (2)
O2A—C8A—C9A—C1A159.8 (2)O2B—C8B—C9B—C10B77.0 (3)
C7A—C8A—C9A—C1A17.2 (2)C7B—C8B—C9B—C10B105.17 (19)
O1A—C1A—C9A—N1A35.7 (3)O1B—C1B—C9B—N1B37.1 (3)
C2A—C1A—C9A—N1A140.44 (18)C2B—C1B—C9B—N1B139.27 (18)
O1A—C1A—C9A—C8A160.0 (2)O1B—C1B—C9B—C8B162.2 (2)
C2A—C1A—C9A—C8A16.1 (2)C2B—C1B—C9B—C8B14.1 (2)
O1A—C1A—C9A—C10A78.5 (3)O1B—C1B—C9B—C10B77.1 (3)
C2A—C1A—C9A—C10A105.37 (19)C2B—C1B—C9B—C10B106.56 (19)
N1A—C9A—C10A—C11A167.79 (17)N1B—C9B—C10B—C11B168.47 (17)
C8A—C9A—C10A—C11A69.6 (2)C8B—C9B—C10B—C11B69.4 (2)
C1A—C9A—C10A—C11A44.1 (2)C1B—C9B—C10B—C11B44.7 (2)
N1A—C9A—C10A—C18A72.5 (2)N1B—C9B—C10B—C18B72.8 (2)
C8A—C9A—C10A—C18A50.1 (2)C8B—C9B—C10B—C18B49.4 (2)
C1A—C9A—C10A—C18A163.79 (17)C1B—C9B—C10B—C18B163.45 (17)
N1A—C9A—C10A—C19A47.83 (18)N1B—C9B—C10B—C19B47.22 (18)
C8A—C9A—C10A—C19A170.43 (16)C8B—C9B—C10B—C19B169.36 (16)
C1A—C9A—C10A—C19A75.89 (19)C1B—C9B—C10B—C19B76.55 (19)
C18A—C10A—C11A—O3A178.3 (2)C18B—C10B—C11B—O3B176.0 (2)
C9A—C10A—C11A—O3A57.7 (3)C19B—C10B—C11B—O3B51.0 (3)
C19A—C10A—C11A—O3A53.8 (3)C9B—C10B—C11B—O3B61.5 (3)
C18A—C10A—C11A—C12A1.5 (2)C18B—C10B—C11B—C12B4.8 (2)
C9A—C10A—C11A—C12A122.43 (19)C19B—C10B—C11B—C12B129.81 (19)
C19A—C10A—C11A—C12A125.99 (18)C9B—C10B—C11B—C12B117.67 (19)
O3A—C11A—C12A—C17A179.3 (2)O3B—C11B—C12B—C17B179.0 (2)
C10A—C11A—C12A—C17A0.5 (2)C10B—C11B—C12B—C17B1.9 (2)
O3A—C11A—C12A—C13A0.5 (4)O3B—C11B—C12B—C13B0.8 (4)
C10A—C11A—C12A—C13A179.4 (2)C10B—C11B—C12B—C13B178.4 (2)
C17A—C12A—C13A—C14A0.3 (3)C17B—C12B—C13B—C14B0.3 (3)
C11A—C12A—C13A—C14A178.4 (2)C11B—C12B—C13B—C14B179.9 (2)
C12A—C13A—C14A—C15A0.2 (3)C12B—C13B—C14B—C15B0.8 (3)
C13A—C14A—C15A—C16A0.1 (3)C13B—C14B—C15B—C16B1.2 (3)
C14A—C15A—C16A—C17A0.4 (3)C14B—C15B—C16B—C17B0.5 (3)
C15A—C16A—C17A—C12A0.3 (3)C15B—C16B—C17B—C12B0.6 (3)
C15A—C16A—C17A—C18A177.5 (2)C15B—C16B—C17B—C18B177.9 (2)
C13A—C12A—C17A—C16A0.1 (3)C13B—C12B—C17B—C16B1.1 (3)
C11A—C12A—C17A—C16A178.88 (19)C11B—C12B—C17B—C16B179.18 (19)
C13A—C12A—C17A—C18A178.18 (19)C13B—C12B—C17B—C18B177.67 (19)
C11A—C12A—C17A—C18A0.8 (2)C11B—C12B—C17B—C18B2.1 (2)
C16A—C17A—C18A—C10A179.6 (2)C16B—C17B—C18B—C10B176.3 (2)
C12A—C17A—C18A—C10A1.7 (2)C12B—C17B—C18B—C10B5.1 (2)
C11A—C10A—C18A—C17A1.9 (2)C11B—C10B—C18B—C17B5.8 (2)
C9A—C10A—C18A—C17A122.81 (18)C19B—C10B—C18B—C17B131.00 (18)
C19A—C10A—C18A—C17A125.90 (18)C9B—C10B—C18B—C17B117.94 (18)
C11A—C10A—C19A—C20A65.5 (2)C11B—C10B—C19B—C20B65.9 (2)
C18A—C10A—C19A—C20A54.2 (2)C18B—C10B—C19B—C20B54.4 (2)
C9A—C10A—C19A—C20A173.76 (17)C9B—C10B—C19B—C20B173.00 (16)
C11A—C10A—C19A—C26A163.90 (17)C11B—C10B—C19B—C26B164.37 (17)
C18A—C10A—C19A—C26A76.4 (2)C18B—C10B—C19B—C26B75.3 (2)
C9A—C10A—C19A—C26A43.20 (18)C9B—C10B—C19B—C26B43.31 (18)
C26A—C19A—C20A—C21A25.0 (3)C26B—C19B—C20B—C25B151.2 (2)
C10A—C19A—C20A—C21A97.8 (2)C10B—C19B—C20B—C25B87.3 (2)
C26A—C19A—C20A—C25A151.99 (19)C26B—C19B—C20B—C21B28.3 (3)
C10A—C19A—C20A—C25A85.2 (2)C10B—C19B—C20B—C21B93.2 (2)
C25A—C20A—C21A—C22A2.3 (3)C25B—C20B—C21B—C22B1.3 (3)
C19A—C20A—C21A—C22A174.7 (2)C19B—C20B—C21B—C22B178.1 (2)
C20A—C21A—C22A—C23A1.4 (3)C20B—C21B—C22B—C23B0.6 (3)
C21A—C22A—C23A—C24A0.7 (3)C21B—C22B—C23B—C24B0.9 (4)
C22A—C23A—C24A—C25A1.9 (3)C22B—C23B—C24B—C25B1.8 (4)
C23A—C24A—C25A—C20A0.9 (4)C23B—C24B—C25B—C20B1.1 (4)
C21A—C20A—C25A—C24A1.2 (3)C21B—C20B—C25B—C24B0.5 (3)
C19A—C20A—C25A—C24A176.0 (2)C19B—C20B—C25B—C24B179.0 (2)
C9A—N1A—C26A—C27A115.77 (18)C9B—N1B—C26B—C27B116.42 (18)
C28A—N1A—C26A—C27A18.3 (2)C28B—N1B—C26B—C27B19.8 (2)
C9A—N1A—C26A—C19A7.9 (2)C9B—N1B—C26B—C19B7.2 (2)
C28A—N1A—C26A—C19A142.03 (17)C28B—N1B—C26B—C19B143.38 (17)
C20A—C19A—C26A—N1A153.37 (17)C20B—C19B—C26B—N1B151.82 (18)
C10A—C19A—C26A—N1A23.1 (2)C10B—C19B—C26B—N1B23.7 (2)
C20A—C19A—C26A—C27A87.6 (2)C20B—C19B—C26B—C27B90.0 (2)
C10A—C19A—C26A—C27A142.16 (18)C10B—C19B—C26B—C27B141.83 (18)
N1A—C26A—C27A—S1A36.06 (19)N1B—C26B—C27B—S1B37.88 (19)
C19A—C26A—C27A—S1A152.76 (16)C19B—C26B—C27B—S1B153.91 (16)
C28A—S1A—C27A—C26A35.51 (16)C28B—S1B—C27B—C26B37.12 (16)
C9A—N1A—C28A—S1A138.76 (15)C9B—N1B—C28B—S1B140.55 (15)
C26A—N1A—C28A—S1A8.4 (2)C26B—N1B—C28B—S1B8.0 (2)
C27A—S1A—C28A—N1A25.99 (16)C27B—S1B—C28B—N1B26.63 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15A—H15A···O2Ai0.952.513.235 (3)134
C16B—H16B···N1Bii0.952.483.383 (3)159
C18B—H18B···O2B0.992.333.070 (4)131
C18A—H18C···O2A0.992.403.167 (4)133
C19A—H19A···O1A1.002.373.075 (4)127
C19B—H19B···O1B1.002.403.086 (4)125
C23A—H23A···O1Biii0.952.503.209 (4)132
C23B—H23B···O1A0.952.583.227 (4)126
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y, z+2; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC28H21NO3S
Mr451.52
Crystal system, space groupMonoclinic, P2/c
Temperature (K)100
a, b, c (Å)19.3315 (6), 9.6523 (3), 29.9731 (8)
β (°) 127.817 (2)
V3)4418.1 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.44 × 0.22 × 0.16
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.925, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
47347, 12947, 7530
Rint0.067
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.155, 1.02
No. of reflections12947
No. of parameters595
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.49

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
C15A—H15A···O2Ai0.952.513.235 (3)134
C16B—H16B···N1Bii0.952.483.383 (3)159
C18B—H18B···O2B0.992.333.070 (4)131
C18A—H18C···O2A0.992.403.167 (4)133
C19A—H19A···O1A1.002.373.075 (4)127
C19B—H19B···O1B1.002.403.086 (4)125
C23A—H23A···O1Biii0.952.503.209 (4)132
C23B—H23B···O1A0.952.583.227 (4)126
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y, z+2; (iii) x1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors wish to express their thanks to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti Sains Malysia (USM), Penang, for funding of this work through Research Grant No. RUC (1001/PSK/8620012). HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationKumar, R. S., Osman, H., Ali, M. A., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o1540–o1541.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWei, A. C., Ali, M. A., Choon, T. S., Quah, C. K. & Fun, H.-K. (2011a). Acta Cryst. E67, o2383.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWei, A. C., Ali, M. A., Ismail, R., Quah, C. K. & Fun, H.-K. (2011b). Acta Cryst. E67, o2381–o2382.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011c). Acta Cryst. E67, o2404.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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