Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 4| April 2014| Pages o395-o396
doi:10.1107/S1600536814004577

(E)-2-[4-(Di­ethyl­amino)­styr­yl]-1-methyl­quinolin-1-ium 4-chloro­benzene­sulfonate monohydrate

Suchada Chantrapromma,a*‡ Narissara Kaewmanee,a Nawong Boonnak,b Ching Kheng Quahc and Hoong-Kun Func§

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: suchada.c@psu.ac.th

(Received 3 February 2014; accepted 14 February 2014; online 5 March 2014)

The asymmetric unit of the title hydrated salt, C22H25N2+·C6H4ClO3S−·H2O, comprises two 2-[4-(di­ethyl­amino)­styr­yl]-1-methyl­quinolin-1-ium cations, two 4-chloro­benzene­sul­fon­ate anions and two solvent water mol­ecules. One ethyl group of both cations displays disorder over two positions in a 0.659 (2):0.341 (2) ratio in one mol­ecule and in a 0.501 (2):0.499 (2) ratio in the other. The sulfonate group of one anion is also disordered over two positions in a 0.893 (7):0.107 (7) ratio. The dihedral angle between the mean plane of the quinolinium ring system and that of benzene ring is 10.57 (18)° in one cation and 14.4 (2)° in the other. In the crystal, cations, anions and water mol­ecules are linked into chains along the [010] direction by O—H⋯Osulfonate hydrogen bonds, together with weak C—H⋯Osulfonate and C—H⋯Cl inter­actions. The cations are stacked by π–π inter­actions, with centroid–centroid distances in the range 3.675 (2)–4.162 (3) Å.

CCDC reference: 988937

Related literature

For standard bond lengths, 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-S19.]). For background to and applications of quarternary ammonium compounds, see: Barchéchath et al. (2005[Barchéchath, S. D., Tawatao, R. I., Corr, M., Carson, D. A. & Cottam, H. B. (2005). Bioorg. Med. Chem. Lett. 15, 1785-1788.]); Chanawanno et al. (2010a[Chanawanno, K., Chantrapromma, S., Anantapong, T. & Kanjana-Opas, A. (2010a). Lat. Am. J. Pharm. 29, 1166-1170.],b[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010b). Eur. J. Med. Chem. 45, 4199-4208.]); Bolden et al. (2013[Bolden, S. Jr, Zhu, X. Y., Etukala, J. R., Boateng, C., Mazu, T., Flores-Rozas, H., Jacob, M. R., Khan, S. I., Walker, L. A. & Ablordeppey, S. Y. (2013). Eur. J. Med. Chem. 70, 130-142.]). For related structures, see: Chantrapromma et al. (2012[Chantrapromma, S., Kaewmanee, N., Boonnak, N., Anantapong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o2728-o2729.]); Fun, Kaewmanee et al. (2011[Fun, H.-K., Kaewmanee, N., Chanawanno, K. & Chantrapromma, S. (2011). Acta Cryst. E67, o593-o594.], 2013[Fun, H.-K., Kaewmanee, N., Chanawanno, K., Boonnak, N. & Chantrapromma, S. (2013). Acta Cryst. E69, o1510-o1511.]); Kaewmanee et al. (2010[Kaewmanee, N., Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o2639-o2640.]). 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

  • C22H25N2+·C6H4ClO3S−·H2O

  • Mr = 527.07

  • Monoclinic, P 21 /c

  • a = 25.814 (4) Å

  • b = 10.5563 (16) Å

  • c = 20.333 (3) Å

  • β = 110.883 (2)°

  • V = 5176.8 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 100 K

  • 0.31 × 0.19 × 0.15 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 = 0.923, Tmax = 0.961

  • 28821 measured reflections

  • 10657 independent reflections

  • 6269 reflections with I > 2σ(I)

  • Rint = 0.064
Refinement

  • R[F2 > 2σ(F2)] = 0.076

  • wR(F2) = 0.201

  • S = 1.04

  • 10657 reflections

  • 708 parameters

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1WB—H1WB⋯O1Bi 0.85 2.36 2.815 (7) 114
O1WB—H2WB⋯O2Bii 0.83 2.12 2.953 (7) 177
O1WA—H1WA⋯O2Aiii 0.84 2.07 2.891 (5) 166
O1WA—H2WA⋯O1A 0.76 2.10 2.844 (4) 169
C8A—H8AA⋯O3Aiv 0.93 2.54 3.146 (5) 123
C2B—H2BA⋯O3Bv 0.93 2.57 3.314 (7) 137
C11B—H11B⋯O1Bvi 0.93 2.41 3.237 (6) 148
C18Y—H18E⋯Cl1Avii 0.97 2.72 3.673 (19) 169
C19B—H19D⋯Cl1Bviii 0.96 2.73 3.531 (14) 142
C22B—H22D⋯O2Bviii 0.96 2.55 3.259 (7) 131
C25A—H25A⋯O3Aii 0.93 2.56 3.359 (5) 144
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z; (v) x+1, y, z+1; (vi) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (vii) -x+1, -y, -z+1; (viii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 988937

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814004577/sj5390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004577/sj5390Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004577/sj5390Isup3.cml

checkCIF report


Comment top

The bioactivity of compounds containing the quinolinium chemophore has been the subject of a number of reports (Barchéchath et al., 2005; Chanawanno et al., 2010a, 2010b and Bolden et al., 2013). The title quinolinium derivative (I) was synthesized and tested for antibacterial activities against gram positive bacteria including Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococcus faecalis, and gram negative bacteria including Pseudomonas aeruginosa, Shigella sonnei and Salmonella typhi. Our antibacterial assay has shown that (I) is strongly active against B. subtilis and P. aeruginosa with a minimum inhibition concentration (MIC) of 9.37 µg/ml for both strains. In addition (I) also showed moderate activity against E. faecalis with an MIC value of 37.5 µg/ml. Herein the crystal structure of (I) is reported.

The asymmetric unit of the title compound (I) (Fig. 1) consists of two C22H25N2+ cations, two C6H4ClO3S- anions and two solvent H2O molecules [the two molecules are denoted as molecules A and B]. One ethyl unit of diethylamino group of both cation molecules displays disorder over two positions with refined site occupancy ratios of 0.659 (2):0.341 (2) and 0.501 (2):0.499 (2) for molecules A and B, respectively. The sulfonate group of the anion B also shows disorder over two positions with a refined site occupancy ratio of 0.893 (7):0.107 (7). The cations exist in the E configuration with respect to the C10═C11 double bond [1.343 (6) Å] and the torsion angle is C9–C10–C11–C12 of 174.6 (4)° for molecule A [the corresponding values are 1.324 (6) Å and -172.5 (4)° for molecule B]. The C1–C9/N1 quinolinium ring system is essentially planar with r.m.s. deviations of 0.0293 (4) and 0.0198 (5) Å for molecules A and B, respectively. The dihedral angle between the mean-plane of the quinolinium ring system and that of C12–C17 benzene ring is 10.57 (18) and 14.4 (2) ° for molecules A and B, respectively. The disorder of the ethyl groups in each cation result in the diethylamino substituents having two different configurations in which the two ethyl groups either point away from one another (Fig. 1 and Fig. 2), or towards one another (Fig. 1 and Fig. 3). The diethylamino substituents also deviate from the planes of the benzene rings to which they are attached as indicated by the torsion angles C15A–N2A–C18A–C19A = -84.1 (7)° and C15A–N2A–C20A–C21A = -96.3 (8)° (major component A) and C15A–N2A–C20X–C21X = 100.0 (11)° (minor component X). In molecule B, the torsion angles C15B–N2B–C20B–C21B = 79.0 (8)° and C15B–N2B–C18B–C19B = -83.7 (10)° (major component B) and C15B–N2B–C18Y–C19Y = 112.6 (10)° (minor component Y). The bond lengths are in normal ranges (Allen et al., 1987) and comparable to those found in some closely related structures (Chantrapromma et al., 2012; Fun, Kaewmanee et al., 2011, 2013 and Kaewmanee et al., 2010).

In the crystal packing, the cations, anions and water molecules are linked into chains along the [0 1 0] direction by O—H···Osulfonate hydrogen bonds together with weak C—H···Osulfonate and C—H···Cl interactions (Fig. 4 and Table 1). The cations are stacked through π–π interactions with the centroid distances Cg1···Cg1iv = 3.675 (2) Å, Cg1···Cg2iv = 4.106 (3) Å, Cg1···Cg3ix = 4.018 (3) Å, Cg16···Cg16x = 3.687 (3) Å, Cg16···Cg17x = 3.714 (3) Å and Cg16···Cg18xi = 4.162 (3) Å [symmetry codes are as in in Table 1 and (ix) = 1-x, -y, -z; (x) = 2-x, 2-y, 2-z and (xi) = 2-x, 1-y, 2-z]; Cg1, Cg2, Cg3, Cg16, Cg17 and Cg18 are the centroids of the N1A/C1A/C6A–C9A, C1A–C6A, C12A–C17A, N1B/C1B/C6B–C9B, C1B–C6B and C12B–C17B rings, respectively. Fig. 5 shows these π···π interactions only for the major disorder components.

Related literature top

For standard bond lengths, see: Allen et al. (1987). For background to and applications of quarternary ammonium compounds, see: Barchéchath et al. (2005); Chanawanno et al. (2010a, 2010b); Bolden et al. (2013). For related structures, see: Chantrapromma et al. (2012); Fun, Kaewmanee et al. (2011, 2013); Kaewmanee et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was prepared by stirring silver (I) 4-chlorobenzenesulfonate (0.95 g, 3.16 mmol) and (E)-2-(4-(diethylamino)styryl)-1-methylquinolinium iodide (1.44 g, 3.16 mmol) in methanol (100 ml) for ca. 0.5 h. The precipitate of silver iodide which formed was filtered out and the filtrate was evaporated to give the title compound as a brown solid. Brown block-shaped single crystals of the title compound suitable for X-ray structure determination was recrystallized from ethanol by slow evaporation at room temperature over a few weeks, Mp. 471-473 K.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms with d(O-H) = 0.76-0.85 Å, d(C-H) = 0.93 Å for aromatic and CH, 0.97 Å for CH2 and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for water and methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The two cations (molecules A and B) and one anion (molecule B) are disordered over two sites with refined site occupancies ratios of 0.659 (2):0.0.341 (2), 0.501 (2):0.499 (2) and 0.893 (7):0.107 (7), respectively.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (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), PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) showing 40% probability displacement ellipsoids and the atom-numbering scheme. Open bonds show the minor disorder component.
[Figure 2] Fig. 2. The molecular structure of the major component A showing the configuration of diethylamino group. Only cation A is shown.
[Figure 3] Fig. 3. The molecular structure of the minor component X showing the configuration of diethylamino group which differs from that of the major component A. Only cation A is shown.
[Figure 4] Fig. 4. The crystal packing of the major component viewed along the a axis showing chains running along the b axis. The O—H···O hydrogen bonds and weak C—H···O and C—H···Cl interactions are drawn as dashed lines.
[Figure 5] Fig. 5. π–π interactions between the aromatic rings of the major disorder components of the cations.
(E)-2-[4-(Diethylamino)styryl]-1-methylquinolin-1-ium 4-fluorobenzenesulfonate monohydrate top
Crystal data top
C22H25N2+·C6H4ClO3S−·H2OF(000) = 2224
Mr = 527.07Dx = 1.352 Mg m−3
Monoclinic, P21/cMelting point = 471–473 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 25.814 (4) ÅCell parameters from 10657 reflections
b = 10.5563 (16) Åθ = 2–26.5°
c = 20.333 (3) ŵ = 0.27 mm−1
β = 110.883 (2)°T = 100 K
V = 5176.8 (14) Å3Block, brown
Z = 80.31 × 0.19 × 0.15 mm
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		10657 independent reflections
Radiation source: fine-focus sealed tube6269 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ϕ and ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −30→32
Tmin = 0.923, Tmax = 0.961k = −13→13
28821 measured reflectionsl = −25→25
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)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0652P)2 + 7.6849P]
where P = (Fo2 + 2Fc2)/3
10657 reflections(Δ/σ)max = 0.001
708 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C22H25N2+·C6H4ClO3S−·H2OV = 5176.8 (14) Å3
Mr = 527.07Z = 8
Monoclinic, P21/cMo Kα radiation
a = 25.814 (4) ŵ = 0.27 mm−1
b = 10.5563 (16) ÅT = 100 K
c = 20.333 (3) Å0.31 × 0.19 × 0.15 mm
β = 110.883 (2)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		10657 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		6269 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.961Rint = 0.064
28821 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0760 restraints
wR(F2) = 0.201H-atom parameters constrained
S = 1.04Δρmax = 0.61 e Å−3
10657 reflectionsΔρmin = −0.43 e Å−3
708 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*/UeqOcc. (<1)
Cl1A0.27801 (5)0.17454 (13)0.13432 (7)0.0684 (4)
S1A0.46207 (4)0.58226 (11)0.26409 (5)0.0415 (3)
O1A0.43655 (13)0.6836 (3)0.29041 (14)0.0512 (8)
O2A0.50670 (12)0.5209 (3)0.31975 (14)0.0578 (9)
O3A0.47678 (12)0.6192 (3)0.20454 (14)0.0538 (8)
C23A0.32927 (17)0.2876 (4)0.17242 (19)0.0404 (10)
C24A0.38262 (17)0.2482 (4)0.2059 (2)0.0411 (10)
H24A0.39150.16250.20900.049*
C25A0.42288 (17)0.3380 (4)0.23497 (18)0.0388 (9)
H25A0.45940.31270.25780.047*
C26A0.40971 (14)0.4651 (4)0.23066 (16)0.0311 (8)
C27A0.35560 (17)0.5029 (4)0.1966 (2)0.0415 (10)
H27A0.34670.58860.19330.050*
C28A0.31469 (17)0.4142 (5)0.1674 (2)0.0483 (11)
H28A0.27800.43890.14470.058*
N1A0.45312 (13)0.3584 (3)0.01622 (15)0.0406 (8)
N2A0.7161 (2)−0.2368 (5)0.1056 (2)0.0799 (15)
C1A0.41975 (15)0.4623 (4)−0.01354 (19)0.0402 (10)
C2A0.39663 (18)0.5404 (5)0.0243 (2)0.0529 (12)
H2AA0.40350.52400.07160.064*
C3A0.3643 (2)0.6400 (5)−0.0077 (3)0.0632 (13)
H3AA0.34920.69090.01830.076*
C4A0.35306 (19)0.6681 (5)−0.0783 (3)0.0570 (12)
H4AA0.32980.7354−0.09950.068*
C5A0.37609 (17)0.5973 (5)−0.1160 (2)0.0520 (12)
H5AA0.36950.6179−0.16270.062*
C6A0.41001 (16)0.4924 (4)−0.0853 (2)0.0443 (10)
C7A0.43683 (17)0.4199 (5)−0.12117 (19)0.0489 (11)
H7AA0.43100.4386−0.16800.059*
C8A0.47081 (18)0.3236 (5)−0.0897 (2)0.0489 (11)
H8AA0.48850.2782−0.11480.059*
C9A0.48013 (15)0.2900 (4)−0.01798 (18)0.0388 (9)
C10A0.51864 (16)0.1924 (4)0.01698 (19)0.0412 (10)
H10A0.52500.17750.06430.049*
C11A0.54617 (16)0.1210 (4)−0.01445 (19)0.0435 (10)
H11A0.53670.1329−0.06260.052*
C12A0.58865 (16)0.0282 (4)0.01772 (18)0.0403 (10)
C13A0.61718 (17)−0.0274 (4)−0.02134 (19)0.0460 (11)
H13A0.6074−0.0054−0.06850.055*
C14A0.65862 (19)−0.1123 (5)0.0065 (2)0.0515 (12)
H14A0.6770−0.1450−0.02170.062*
C15A0.67463 (19)−0.1524 (5)0.0774 (2)0.0515 (11)
C16A0.64536 (18)−0.0960 (4)0.1171 (2)0.0488 (11)
H16A0.6543−0.11900.16400.059*
C17A0.60460 (16)−0.0093 (4)0.08862 (19)0.0443 (10)
H17A0.58680.02610.11670.053*
C18A0.7320 (2)−0.2810 (5)0.1780 (2)0.0714 (15)
H18A0.7491−0.36390.18190.086*
H18B0.6990−0.29010.18990.086*
C19A0.7719 (2)−0.1921 (6)0.2300 (2)0.0733 (16)
H19A0.7793−0.22240.27700.110*
H19B0.7558−0.10910.22510.110*
H19C0.8059−0.18820.22090.110*
C20A0.7593 (5)−0.2587 (10)0.0703 (5)0.056 (3)0.66 (2)
H20A0.7613−0.18550.04240.067*0.66 (2)
H20B0.7957−0.27330.10550.067*0.66 (2)
C21A0.7402 (4)−0.3732 (10)0.0241 (7)0.075 (4)0.66 (2)
H21A0.7679−0.39660.00500.113*0.66 (2)
H21B0.7061−0.3541−0.01370.113*0.66 (2)
H21C0.7343−0.44220.05140.113*0.66 (2)
C20X0.7305 (7)−0.3315 (18)0.0610 (10)0.049 (6)0.34 (2)
H20C0.7008−0.34240.01590.059*0.34 (2)
H20D0.7401−0.41280.08440.059*0.34 (2)
C21X0.7817 (9)−0.265 (2)0.0534 (10)0.057 (5)0.34 (2)
H21D0.7937−0.31110.02090.086*0.34 (2)
H21E0.8111−0.26150.09840.086*0.34 (2)
H21F0.7718−0.18010.03610.086*0.34 (2)
C22A0.45767 (19)0.3216 (5)0.0879 (2)0.0559 (13)
H22A0.46750.23360.09530.084*
H22B0.42270.33520.09360.084*
H22C0.48570.37190.12160.084*
Cl1B0.22680 (5)0.59222 (12)0.37098 (6)0.0612 (3)
S1B0.04143 (5)1.00755 (13)0.30263 (6)0.0579 (3)
O1B−0.00922 (17)0.9418 (5)0.3027 (2)0.0866 (18)0.893 (7)
O2B0.0603 (2)1.0986 (4)0.35813 (19)0.0867 (19)0.893 (7)
O3B0.03461 (16)1.0545 (4)0.23477 (17)0.0595 (13)0.893 (7)
O1Y0.0265 (16)1.006 (4)0.359 (2)0.075 (11)*0.107 (7)
O2Y0.075 (2)1.122 (5)0.278 (3)0.113 (17)*0.107 (7)
O3Y0.0062 (12)0.977 (3)0.2366 (14)0.048 (9)*0.107 (7)
C23B0.17478 (17)0.7065 (4)0.35240 (19)0.0402 (10)
C24B0.18873 (19)0.8286 (5)0.3746 (2)0.0515 (11)
H24B0.22540.85000.39970.062*
C25B0.14773 (19)0.9191 (4)0.3592 (2)0.0501 (11)
H25B0.15701.00210.37410.060*
C26B0.09301 (17)0.8887 (4)0.32205 (19)0.0409 (10)
C27B0.08004 (18)0.7646 (4)0.3010 (2)0.0474 (11)
H27B0.04330.74250.27630.057*
C28B0.12075 (18)0.6726 (4)0.3161 (2)0.0449 (10)
H28B0.11170.58920.30180.054*
N1B1.03757 (14)0.8261 (4)1.05282 (18)0.0477 (9)
N2B0.7638 (2)0.2637 (6)0.8629 (2)0.100 (2)
C1B1.07121 (16)0.9334 (4)1.0564 (2)0.0478 (11)
C2B1.0951 (2)1.0019 (5)1.1184 (3)0.0644 (14)
H2BA1.08960.97671.15920.077*
C3B1.1261 (2)1.1042 (6)1.1192 (3)0.0761 (16)
H3BA1.14211.14851.16110.091*
C4B1.1352 (2)1.1459 (5)1.0598 (4)0.0747 (16)
H4BA1.15711.21701.06230.090*
C5B1.1124 (2)1.0837 (5)0.9981 (3)0.0654 (14)
H5BA1.11851.11170.95810.079*
C6B1.07887 (18)0.9748 (5)0.9949 (3)0.0537 (12)
C7B1.0522 (2)0.9091 (5)0.9319 (3)0.0593 (13)
H7BA1.05710.93550.89090.071*
C8B1.01959 (19)0.8085 (4)0.9299 (2)0.0533 (12)
H8BA1.00210.76710.88730.064*
C9B1.01126 (17)0.7638 (4)0.9921 (2)0.0426 (10)
C10B0.97260 (17)0.6636 (4)0.9875 (2)0.0447 (10)
H10B0.96770.63811.02870.054*
C11B0.94348 (18)0.6051 (4)0.9283 (2)0.0486 (11)
H11B0.95260.62560.88930.058*
C12B0.89936 (17)0.5137 (4)0.9161 (2)0.0441 (10)
C13B0.8711 (2)0.4738 (5)0.8474 (2)0.0578 (13)
H13B0.88230.50460.81180.069*
C14B0.82772 (19)0.3919 (5)0.8300 (2)0.0562 (13)
H14B0.81040.36830.78320.067*
C15B0.8085 (2)0.3420 (5)0.8811 (2)0.0624 (14)
C16B0.8378 (2)0.3800 (6)0.9517 (2)0.0713 (16)
H16B0.82740.34780.98780.086*
C17B0.88144 (19)0.4641 (5)0.9675 (2)0.0527 (12)
H17B0.89940.48841.01410.063*
C18B0.7377 (4)0.2303 (11)0.9135 (6)0.039 (4)0.50 (2)
H18C0.69950.20450.88960.047*0.50 (2)
H18D0.73850.30130.94410.047*0.50 (2)
C19B0.7729 (7)0.1191 (16)0.9558 (7)0.059 (4)0.50 (2)
H19D0.75710.08860.98900.089*0.50 (2)
H19E0.81010.14760.98060.089*0.50 (2)
H19F0.77340.05190.92420.089*0.50 (2)
C18Y0.7654 (8)0.1500 (17)0.9252 (11)0.073 (5)0.50 (2)
H18E0.75750.06540.90550.087*0.50 (2)
H18F0.79980.15050.96550.087*0.50 (2)
C19Y0.7197 (6)0.2047 (14)0.9404 (7)0.081 (5)0.50 (2)
H19G0.71320.15650.97680.122*0.50 (2)
H19H0.68700.20330.89870.122*0.50 (2)
H19I0.72840.29060.95580.122*0.50 (2)
C20B0.7343 (2)0.2220 (6)0.7893 (2)0.0650 (14)
H20E0.73040.29360.75800.078*
H20F0.69740.19360.78450.078*
C21B0.7635 (2)0.1176 (6)0.7675 (3)0.0732 (15)
H21G0.74380.09700.71900.110*
H21H0.76520.04430.79610.110*
H21I0.80050.14420.77330.110*
C22B1.0325 (2)0.7835 (5)1.1179 (2)0.0666 (14)
H22D1.01870.69821.11230.100*
H22E1.00710.83771.12960.100*
H22F1.06810.78651.15500.100*
O1WA0.40302 (13)0.9141 (3)0.21471 (18)0.0667 (9)
H1WB0.91110.84600.22080.100*
H2WB0.91730.78130.16650.100*
O1WB0.9093 (2)0.8517 (5)0.1784 (3)0.1310 (19)
H1WA0.43090.93150.20430.197*
H2WA0.40770.85240.23510.197*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0795 (8)0.0702 (9)0.0648 (7)−0.0410 (7)0.0372 (6)−0.0300 (7)
S1A0.0496 (6)0.0487 (7)0.0280 (4)−0.0144 (5)0.0162 (4)−0.0073 (4)
O1A0.071 (2)0.0453 (18)0.0434 (15)−0.0149 (16)0.0283 (15)−0.0155 (14)
O2A0.0490 (17)0.079 (2)0.0356 (14)−0.0096 (17)0.0026 (13)−0.0031 (15)
O3A0.0645 (19)0.065 (2)0.0391 (15)−0.0277 (17)0.0270 (14)−0.0083 (14)
C23A0.053 (2)0.038 (2)0.0353 (19)−0.017 (2)0.0216 (18)−0.0094 (18)
C24A0.060 (3)0.030 (2)0.044 (2)0.000 (2)0.032 (2)0.0002 (19)
C25A0.047 (2)0.043 (3)0.0308 (18)0.004 (2)0.0203 (17)0.0016 (18)
C26A0.038 (2)0.036 (2)0.0213 (15)−0.0057 (18)0.0139 (14)−0.0020 (15)
C27A0.052 (2)0.032 (2)0.040 (2)0.005 (2)0.0160 (19)0.0017 (18)
C28A0.040 (2)0.055 (3)0.046 (2)−0.002 (2)0.0107 (19)−0.006 (2)
N1A0.0411 (18)0.054 (2)0.0299 (15)−0.0039 (18)0.0160 (14)0.0051 (16)
N2A0.099 (3)0.095 (4)0.047 (2)0.049 (3)0.027 (2)0.018 (2)
C1A0.035 (2)0.048 (3)0.0354 (19)−0.010 (2)0.0100 (16)0.0043 (19)
C2A0.050 (3)0.064 (3)0.051 (2)−0.001 (3)0.026 (2)0.006 (2)
C3A0.056 (3)0.070 (4)0.070 (3)0.003 (3)0.030 (3)0.007 (3)
C4A0.049 (3)0.054 (3)0.064 (3)−0.002 (2)0.014 (2)0.011 (3)
C5A0.039 (2)0.063 (3)0.043 (2)−0.008 (2)0.0005 (19)0.014 (2)
C6A0.036 (2)0.058 (3)0.037 (2)−0.014 (2)0.0114 (17)−0.002 (2)
C7A0.048 (2)0.068 (3)0.0252 (18)−0.011 (2)0.0063 (17)0.008 (2)
C8A0.052 (2)0.063 (3)0.0303 (19)0.001 (2)0.0139 (18)0.007 (2)
C9A0.034 (2)0.051 (3)0.0316 (18)−0.010 (2)0.0125 (16)−0.0017 (18)
C10A0.044 (2)0.053 (3)0.0271 (18)−0.008 (2)0.0129 (17)0.0007 (18)
C11A0.044 (2)0.059 (3)0.0250 (17)−0.012 (2)0.0087 (16)0.0010 (18)
C12A0.041 (2)0.048 (3)0.0304 (18)−0.004 (2)0.0112 (16)0.0003 (18)
C13A0.051 (2)0.059 (3)0.0266 (18)0.003 (2)0.0123 (17)0.0004 (19)
C14A0.062 (3)0.060 (3)0.034 (2)0.011 (3)0.019 (2)−0.001 (2)
C15A0.057 (3)0.056 (3)0.039 (2)0.006 (2)0.013 (2)0.003 (2)
C16A0.058 (3)0.057 (3)0.0323 (19)0.000 (2)0.0169 (19)0.006 (2)
C17A0.044 (2)0.059 (3)0.0317 (19)0.000 (2)0.0153 (17)0.001 (2)
C18A0.087 (4)0.068 (4)0.055 (3)0.025 (3)0.020 (3)0.024 (3)
C19A0.077 (3)0.093 (5)0.048 (3)0.008 (3)0.021 (3)0.033 (3)
C20A0.061 (7)0.045 (5)0.051 (5)0.011 (6)0.008 (4)0.007 (4)
C21A0.089 (7)0.055 (6)0.069 (7)0.016 (5)0.013 (5)0.000 (5)
C20X0.054 (9)0.038 (10)0.051 (10)−0.011 (8)0.014 (7)0.000 (8)
C21X0.056 (12)0.060 (12)0.060 (10)0.004 (9)0.026 (8)0.009 (8)
C22A0.066 (3)0.074 (4)0.036 (2)0.007 (3)0.028 (2)0.011 (2)
Cl1B0.0747 (8)0.0558 (8)0.0571 (6)0.0224 (7)0.0284 (6)−0.0002 (6)
S1B0.0768 (8)0.0564 (8)0.0458 (6)0.0258 (7)0.0285 (6)0.0085 (6)
O1B0.069 (3)0.111 (4)0.102 (3)0.033 (3)0.059 (3)0.043 (3)
O2B0.122 (4)0.082 (3)0.048 (2)0.061 (3)0.020 (2)−0.009 (2)
O3B0.077 (3)0.060 (3)0.0453 (19)0.021 (2)0.0270 (18)0.0125 (18)
C23B0.055 (3)0.038 (2)0.0343 (19)0.011 (2)0.0236 (19)0.0012 (18)
C24B0.050 (3)0.052 (3)0.053 (2)−0.004 (2)0.019 (2)−0.015 (2)
C25B0.065 (3)0.035 (2)0.057 (3)−0.004 (2)0.030 (2)−0.011 (2)
C26B0.051 (2)0.042 (3)0.0334 (19)0.003 (2)0.0192 (18)0.0005 (18)
C27B0.051 (2)0.049 (3)0.043 (2)−0.004 (2)0.0179 (19)−0.011 (2)
C28B0.062 (3)0.033 (2)0.047 (2)−0.005 (2)0.030 (2)−0.0081 (19)
N1B0.050 (2)0.045 (2)0.049 (2)0.0006 (19)0.0180 (16)−0.0041 (17)
N2B0.111 (4)0.154 (5)0.045 (2)−0.086 (4)0.039 (2)−0.033 (3)
C1B0.037 (2)0.037 (3)0.067 (3)0.003 (2)0.015 (2)0.003 (2)
C2B0.052 (3)0.064 (4)0.066 (3)0.000 (3)0.007 (2)−0.010 (3)
C3B0.055 (3)0.062 (4)0.094 (4)−0.006 (3)0.006 (3)−0.013 (3)
C4B0.049 (3)0.048 (3)0.118 (5)−0.005 (3)0.018 (3)−0.008 (4)
C5B0.054 (3)0.049 (3)0.101 (4)0.000 (3)0.035 (3)0.008 (3)
C6B0.043 (2)0.046 (3)0.071 (3)0.010 (2)0.020 (2)−0.005 (2)
C7B0.067 (3)0.058 (3)0.065 (3)0.003 (3)0.038 (3)0.006 (3)
C8B0.063 (3)0.047 (3)0.057 (3)−0.011 (2)0.030 (2)0.000 (2)
C9B0.050 (2)0.035 (2)0.044 (2)0.004 (2)0.0179 (19)−0.0065 (19)
C10B0.052 (2)0.042 (3)0.043 (2)−0.003 (2)0.0211 (19)0.000 (2)
C11B0.064 (3)0.046 (3)0.045 (2)−0.005 (2)0.030 (2)−0.002 (2)
C12B0.055 (2)0.039 (3)0.045 (2)−0.003 (2)0.0257 (19)−0.0014 (19)
C13B0.073 (3)0.063 (3)0.044 (2)−0.019 (3)0.029 (2)−0.010 (2)
C14B0.064 (3)0.070 (4)0.039 (2)−0.013 (3)0.025 (2)−0.009 (2)
C15B0.066 (3)0.084 (4)0.042 (2)−0.030 (3)0.026 (2)−0.014 (2)
C16B0.088 (4)0.096 (4)0.040 (2)−0.040 (3)0.036 (2)−0.018 (3)
C17B0.063 (3)0.057 (3)0.040 (2)−0.011 (3)0.021 (2)−0.013 (2)
C18B0.035 (5)0.045 (7)0.048 (6)−0.016 (5)0.027 (4)−0.013 (5)
C19B0.091 (9)0.045 (9)0.036 (6)−0.021 (7)0.016 (7)0.003 (5)
C18Y0.101 (12)0.045 (10)0.081 (13)−0.007 (9)0.043 (11)−0.007 (9)
C19Y0.082 (10)0.108 (11)0.061 (7)−0.012 (8)0.035 (7)0.011 (7)
C20B0.056 (3)0.085 (4)0.053 (3)−0.021 (3)0.019 (2)−0.020 (3)
C21B0.072 (3)0.073 (4)0.068 (3)−0.008 (3)0.017 (3)−0.003 (3)
C22B0.081 (3)0.069 (4)0.048 (3)−0.011 (3)0.020 (2)−0.003 (2)
O1WA0.0540 (19)0.072 (2)0.074 (2)0.0148 (18)0.0227 (17)0.0020 (19)
O1WB0.103 (4)0.110 (4)0.169 (5)0.040 (3)0.036 (3)0.045 (4)
Geometric parameters (Å, º) top
Cl1A—C23A1.745 (4)S1B—O2B1.430 (4)
S1A—O3A1.446 (3)S1B—O1B1.481 (4)
S1A—O2A1.449 (3)S1B—O2Y1.67 (5)
S1A—O1A1.455 (3)S1B—C26B1.768 (4)
S1A—C26A1.779 (4)C23B—C24B1.371 (6)
C23A—C24A1.366 (6)C23B—C28B1.373 (6)
C23A—C28A1.382 (6)C24B—C25B1.377 (6)
C24A—C25A1.375 (6)C24B—H24B0.9300
C24A—H24A0.9300C25B—C26B1.382 (6)
C25A—C26A1.379 (5)C25B—H25B0.9300
C25A—H25A0.9300C26B—C27B1.382 (6)
C26A—C27A1.378 (5)C27B—C28B1.383 (6)
C27A—C28A1.378 (6)C27B—H27B0.9300
C27A—H27A0.9300C28B—H28B0.9300
C28A—H28A0.9300N1B—C9B1.349 (5)
N1A—C9A1.355 (5)N1B—C1B1.413 (6)
N1A—C1A1.393 (5)N1B—C22B1.448 (5)
N1A—C22A1.473 (5)N2B—C15B1.359 (6)
N2A—C15A1.352 (6)N2B—C18B1.460 (13)
N2A—C18A1.457 (6)N2B—C20B1.483 (6)
N2A—C20X1.48 (2)N2B—C18Y1.74 (2)
N2A—C20A1.546 (15)C1B—C2B1.392 (6)
C1A—C2A1.398 (6)C1B—C6B1.404 (6)
C1A—C6A1.425 (5)C2B—C3B1.341 (7)
C2A—C3A1.356 (7)C2B—H2BA0.9300
C2A—H2AA0.9300C3B—C4B1.381 (8)
C3A—C4A1.392 (6)C3B—H3BA0.9300
C3A—H3AA0.9300C4B—C5B1.351 (8)
C4A—C5A1.350 (6)C4B—H4BA0.9300
C4A—H4AA0.9300C5B—C6B1.426 (7)
C5A—C6A1.411 (6)C5B—H5BA0.9300
C5A—H5AA0.9300C6B—C7B1.402 (7)
C6A—C7A1.400 (6)C7B—C8B1.346 (6)
C7A—C8A1.346 (6)C7B—H7BA0.9300
C7A—H7AA0.9300C8B—C9B1.438 (6)
C8A—C9A1.435 (5)C8B—H8BA0.9300
C8A—H8AA0.9300C9B—C10B1.434 (6)
C9A—C10A1.433 (6)C10B—C11B1.324 (6)
C10A—C11A1.343 (6)C10B—H10B0.9300
C10A—H10A0.9300C11B—C12B1.445 (6)
C11A—C12A1.442 (6)C11B—H11B0.9300
C11A—H11A0.9300C12B—C17B1.387 (5)
C12A—C13A1.391 (5)C12B—C13B1.392 (6)
C12A—C17A1.408 (5)C13B—C14B1.357 (6)
C13A—C14A1.355 (6)C13B—H13B0.9300
C13A—H13A0.9300C14B—C15B1.403 (6)
C14A—C15A1.416 (6)C14B—H14B0.9300
C14A—H14A0.9300C15B—C16B1.422 (6)
C15A—C16A1.418 (6)C16B—C17B1.379 (6)
C16A—C17A1.358 (6)C16B—H16B0.9300
C16A—H16A0.9300C17B—H17B0.9300
C17A—H17A0.9300C18B—C19B1.55 (2)
C18A—C19A1.511 (8)C18B—H18C0.9700
C18A—H18A0.9700C18B—H18D0.9700
C18A—H18B0.9700C19B—H19D0.9600
C19A—H19A0.9600C19B—H19E0.9600
C19A—H19B0.9600C19B—H19F0.9600
C19A—H19C0.9600C18Y—C19Y1.44 (3)
C20A—C21A1.503 (17)C18Y—H18E0.9700
C20A—H20A0.9700C18Y—H18F0.9700
C20A—H20B0.9700C19Y—H19G0.9600
C21A—H21A0.9600C19Y—H19H0.9600
C21A—H21B0.9600C19Y—H19I0.9600
C21A—H21C0.9600C20B—C21B1.490 (7)
C20X—C21X1.55 (3)C20B—H20E0.9700
C20X—H20C0.9700C20B—H20F0.9700
C20X—H20D0.9700C21B—H21G0.9600
C21X—H21D0.9600C21B—H21H0.9600
C21X—H21E0.9600C21B—H21I0.9600
C21X—H21F0.9600C22B—H22D0.9600
C22A—H22A0.9600C22B—H22E0.9600
C22A—H22B0.9600C22B—H22F0.9600
C22A—H22C0.9600O1WA—H1WA0.8388
Cl1B—C23B1.743 (4)O1WA—H2WA0.7583
S1B—O1Y1.34 (4)O1WB—H1WB0.8496
S1B—O3Y1.36 (3)O1WB—H2WB0.8297
S1B—O3B1.417 (3)
O3A—S1A—O2A113.70 (18)O2B—S1B—O1B111.5 (3)
O3A—S1A—O1A113.45 (19)O1Y—S1B—O2Y127 (2)
O2A—S1A—O1A112.33 (18)O3Y—S1B—O2Y96 (2)
O3A—S1A—C26A104.97 (16)O3B—S1B—O2Y49.6 (17)
O2A—S1A—C26A105.79 (19)O2B—S1B—O2Y71.5 (17)
O1A—S1A—C26A105.65 (17)O1B—S1B—O2Y153.8 (17)
C24A—C23A—C28A122.1 (4)O1Y—S1B—C26B103.0 (16)
C24A—C23A—Cl1A118.9 (3)O3Y—S1B—C26B103.8 (12)
C28A—C23A—Cl1A119.0 (3)O3B—S1B—C26B106.73 (19)
C23A—C24A—C25A118.6 (4)O2B—S1B—C26B106.4 (2)
C23A—C24A—H24A120.7O1B—S1B—C26B105.2 (2)
C25A—C24A—H24A120.7O2Y—S1B—C26B98.3 (16)
C24A—C25A—C26A120.8 (4)C24B—C23B—C28B121.3 (4)
C24A—C25A—H25A119.6C24B—C23B—Cl1B119.2 (3)
C26A—C25A—H25A119.6C28B—C23B—Cl1B119.5 (3)
C27A—C26A—C25A119.7 (4)C23B—C24B—C25B119.2 (4)
C27A—C26A—S1A119.1 (3)C23B—C24B—H24B120.4
C25A—C26A—S1A121.0 (3)C25B—C24B—H24B120.4
C28A—C27A—C26A120.2 (4)C24B—C25B—C26B121.1 (4)
C28A—C27A—H27A119.9C24B—C25B—H25B119.5
C26A—C27A—H27A119.9C26B—C25B—H25B119.5
C27A—C28A—C23A118.6 (4)C25B—C26B—C27B118.5 (4)
C27A—C28A—H28A120.7C25B—C26B—S1B119.9 (3)
C23A—C28A—H28A120.7C27B—C26B—S1B121.6 (3)
C9A—N1A—C1A123.2 (3)C26B—C27B—C28B121.1 (4)
C9A—N1A—C22A119.6 (4)C26B—C27B—H27B119.5
C1A—N1A—C22A117.2 (3)C28B—C27B—H27B119.5
C15A—N2A—C18A122.4 (4)C23B—C28B—C27B118.8 (4)
C15A—N2A—C20X121.1 (7)C23B—C28B—H28B120.6
C18A—N2A—C20X111.1 (7)C27B—C28B—H28B120.6
C15A—N2A—C20A119.6 (5)C9B—N1B—C1B122.5 (4)
C18A—N2A—C20A115.6 (5)C9B—N1B—C22B120.3 (4)
N1A—C1A—C2A123.0 (3)C1B—N1B—C22B117.2 (4)
N1A—C1A—C6A118.5 (4)C15B—N2B—C18B121.0 (5)
C2A—C1A—C6A118.5 (4)C15B—N2B—C20B122.5 (4)
C3A—C2A—C1A120.3 (4)C18B—N2B—C20B116.0 (5)
C3A—C2A—H2AA119.9C15B—N2B—C18Y115.2 (7)
C1A—C2A—H2AA119.9C20B—N2B—C18Y113.6 (7)
C2A—C3A—C4A121.7 (5)C2B—C1B—C6B119.1 (5)
C2A—C3A—H3AA119.2C2B—C1B—N1B121.9 (4)
C4A—C3A—H3AA119.2C6B—C1B—N1B118.9 (4)
C5A—C4A—C3A119.7 (5)C3B—C2B—C1B120.0 (5)
C5A—C4A—H4AA120.2C3B—C2B—H2BA120.0
C3A—C4A—H4AA120.2C1B—C2B—H2BA120.0
C4A—C5A—C6A120.9 (4)C2B—C3B—C4B122.2 (6)
C4A—C5A—H5AA119.6C2B—C3B—H3BA118.9
C6A—C5A—H5AA119.6C4B—C3B—H3BA118.9
C7A—C6A—C5A122.9 (4)C5B—C4B—C3B120.2 (5)
C7A—C6A—C1A118.2 (4)C5B—C4B—H4BA119.9
C5A—C6A—C1A118.9 (4)C3B—C4B—H4BA119.9
C8A—C7A—C6A121.7 (4)C4B—C5B—C6B119.5 (5)
C8A—C7A—H7AA119.2C4B—C5B—H5BA120.3
C6A—C7A—H7AA119.2C6B—C5B—H5BA120.3
C7A—C8A—C9A121.0 (4)C7B—C6B—C1B118.7 (4)
C7A—C8A—H8AA119.5C7B—C6B—C5B122.2 (5)
C9A—C8A—H8AA119.5C1B—C6B—C5B119.0 (5)
N1A—C9A—C10A121.4 (3)C8B—C7B—C6B121.1 (4)
N1A—C9A—C8A117.3 (4)C8B—C7B—H7BA119.5
C10A—C9A—C8A121.2 (4)C6B—C7B—H7BA119.5
C11A—C10A—C9A124.0 (3)C7B—C8B—C9B121.3 (4)
C11A—C10A—H10A118.0C7B—C8B—H8BA119.3
C9A—C10A—H10A118.0C9B—C8B—H8BA119.3
C10A—C11A—C12A127.7 (3)N1B—C9B—C10B122.1 (4)
C10A—C11A—H11A116.2N1B—C9B—C8B117.4 (4)
C12A—C11A—H11A116.2C10B—C9B—C8B120.3 (4)
C13A—C12A—C17A116.4 (4)C11B—C10B—C9B124.0 (4)
C13A—C12A—C11A120.0 (3)C11B—C10B—H10B118.0
C17A—C12A—C11A123.6 (4)C9B—C10B—H10B118.0
C14A—C13A—C12A122.7 (4)C10B—C11B—C12B128.6 (4)
C14A—C13A—H13A118.6C10B—C11B—H11B115.7
C12A—C13A—H13A118.6C12B—C11B—H11B115.7
C13A—C14A—C15A121.6 (4)C17B—C12B—C13B116.5 (4)
C13A—C14A—H14A119.2C17B—C12B—C11B125.3 (4)
C15A—C14A—H14A119.2C13B—C12B—C11B118.2 (4)
N2A—C15A—C14A121.9 (4)C14B—C13B—C12B122.9 (4)
N2A—C15A—C16A122.5 (4)C14B—C13B—H13B118.6
C14A—C15A—C16A115.6 (4)C12B—C13B—H13B118.6
C17A—C16A—C15A122.0 (4)C13B—C14B—C15B121.5 (4)
C17A—C16A—H16A119.0C13B—C14B—H14B119.2
C15A—C16A—H16A119.0C15B—C14B—H14B119.2
C16A—C17A—C12A121.7 (4)N2B—C15B—C14B121.1 (4)
C16A—C17A—H17A119.2N2B—C15B—C16B122.8 (4)
C12A—C17A—H17A119.2C14B—C15B—C16B116.1 (4)
N2A—C18A—C19A112.6 (5)C17B—C16B—C15B120.9 (4)
N2A—C18A—H18A109.1C17B—C16B—H16B119.6
C19A—C18A—H18A109.1C15B—C16B—H16B119.6
N2A—C18A—H18B109.1C16B—C17B—C12B122.1 (4)
C19A—C18A—H18B109.1C16B—C17B—H17B118.9
H18A—C18A—H18B107.8C12B—C17B—H17B118.9
C18A—C19A—H19A109.5N2B—C18B—C19B104.4 (10)
C18A—C19A—H19B109.5N2B—C18B—H18C110.9
H19A—C19A—H19B109.5C19B—C18B—H18C110.9
C18A—C19A—H19C109.5N2B—C18B—H18D110.9
H19A—C19A—H19C109.5C19B—C18B—H18D110.9
H19B—C19A—H19C109.5H18C—C18B—H18D108.9
C21A—C20A—N2A106.3 (12)C19Y—C18Y—N2B94.1 (15)
C21A—C20A—H20A110.5C19Y—C18Y—H18E112.9
N2A—C20A—H20A110.5N2B—C18Y—H18E112.9
C21A—C20A—H20B110.5C19Y—C18Y—H18F112.9
N2A—C20A—H20B110.5N2B—C18Y—H18F112.9
H20A—C20A—H20B108.7H18E—C18Y—H18F110.3
N2A—C20X—C21X99.4 (16)C18Y—C19Y—H19G109.5
N2A—C20X—H20C111.9C18Y—C19Y—H19H109.5
C21X—C20X—H20C111.9H19G—C19Y—H19H109.5
N2A—C20X—H20D111.9C18Y—C19Y—H19I109.5
C21X—C20X—H20D111.9H19G—C19Y—H19I109.5
H20C—C20X—H20D109.6H19H—C19Y—H19I109.5
C20X—C21X—H21D109.5N2B—C20B—C21B112.8 (5)
C20X—C21X—H21E109.5N2B—C20B—H20E109.0
H21D—C21X—H21E109.5C21B—C20B—H20E109.0
C20X—C21X—H21F109.5N2B—C20B—H20F109.0
H21D—C21X—H21F109.5C21B—C20B—H20F109.0
H21E—C21X—H21F109.5H20E—C20B—H20F107.8
N1A—C22A—H22A109.5C20B—C21B—H21G109.5
N1A—C22A—H22B109.5C20B—C21B—H21H109.5
H22A—C22A—H22B109.5H21G—C21B—H21H109.5
N1A—C22A—H22C109.5C20B—C21B—H21I109.5
H22A—C22A—H22C109.5H21G—C21B—H21I109.5
H22B—C22A—H22C109.5H21H—C21B—H21I109.5
O1Y—S1B—O3Y123 (2)N1B—C22B—H22D109.5
O1Y—S1B—O3B150.2 (16)N1B—C22B—H22E109.5
O3Y—S1B—O3B46.8 (13)H22D—C22B—H22E109.5
O1Y—S1B—O2B56.5 (18)N1B—C22B—H22F109.5
O3Y—S1B—O2B148.7 (12)H22D—C22B—H22F109.5
O3B—S1B—O2B115.0 (3)H22E—C22B—H22F109.5
O1Y—S1B—O1B58.0 (18)H1WA—O1WA—H2WA110.0
O3Y—S1B—O1B67.2 (13)H1WB—O1WB—H2WB107.8
O3B—S1B—O1B111.2 (3)
C28A—C23A—C24A—C25A−0.4 (5)C24B—C25B—C26B—C27B0.6 (6)
Cl1A—C23A—C24A—C25A179.1 (3)C24B—C25B—C26B—S1B−179.5 (3)
C23A—C24A—C25A—C26A0.2 (5)O1Y—S1B—C26B—C25B−88.0 (19)
C24A—C25A—C26A—C27A−0.3 (5)O3Y—S1B—C26B—C25B142.4 (14)
C24A—C25A—C26A—S1A−176.7 (3)O3B—S1B—C26B—C25B93.9 (4)
O3A—S1A—C26A—C27A−83.0 (3)O2B—S1B—C26B—C25B−29.4 (4)
O2A—S1A—C26A—C27A156.5 (3)O1B—S1B—C26B—C25B−147.9 (4)
O1A—S1A—C26A—C27A37.2 (3)O2Y—S1B—C26B—C25B43.6 (18)
O3A—S1A—C26A—C25A93.5 (3)O1Y—S1B—C26B—C27B91.9 (19)
O2A—S1A—C26A—C25A−27.0 (3)O3Y—S1B—C26B—C27B−37.7 (14)
O1A—S1A—C26A—C25A−146.3 (3)O3B—S1B—C26B—C27B−86.3 (4)
C25A—C26A—C27A—C28A0.5 (5)O2B—S1B—C26B—C27B150.4 (4)
S1A—C26A—C27A—C28A177.0 (3)O1B—S1B—C26B—C27B32.0 (4)
C26A—C27A—C28A—C23A−0.6 (6)O2Y—S1B—C26B—C27B−136.5 (18)
C24A—C23A—C28A—C27A0.6 (6)C25B—C26B—C27B—C28B−0.6 (6)
Cl1A—C23A—C28A—C27A−178.9 (3)S1B—C26B—C27B—C28B179.6 (3)
C9A—N1A—C1A—C2A−173.2 (4)C24B—C23B—C28B—C27B0.9 (6)
C22A—N1A—C1A—C2A8.1 (6)Cl1B—C23B—C28B—C27B−179.3 (3)
C9A—N1A—C1A—C6A5.0 (6)C26B—C27B—C28B—C23B−0.1 (6)
C22A—N1A—C1A—C6A−173.7 (4)C9B—N1B—C1B—C2B175.6 (4)
N1A—C1A—C2A—C3A−179.7 (4)C22B—N1B—C1B—C2B−4.9 (6)
C6A—C1A—C2A—C3A2.1 (6)C9B—N1B—C1B—C6B−1.8 (6)
C1A—C2A—C3A—C4A−0.1 (7)C22B—N1B—C1B—C6B177.7 (4)
C2A—C3A—C4A—C5A−2.0 (7)C6B—C1B—C2B—C3B−1.6 (7)
C3A—C4A—C5A—C6A2.0 (7)N1B—C1B—C2B—C3B−179.1 (4)
C4A—C5A—C6A—C7A−176.9 (4)C1B—C2B—C3B—C4B0.5 (8)
C4A—C5A—C6A—C1A−0.1 (6)C2B—C3B—C4B—C5B0.3 (8)
N1A—C1A—C6A—C7A−3.2 (6)C3B—C4B—C5B—C6B0.0 (8)
C2A—C1A—C6A—C7A175.0 (4)C2B—C1B—C6B—C7B−176.7 (4)
N1A—C1A—C6A—C5A179.8 (4)N1B—C1B—C6B—C7B0.9 (6)
C2A—C1A—C6A—C5A−1.9 (6)C2B—C1B—C6B—C5B1.9 (6)
C5A—C6A—C7A—C8A177.2 (4)N1B—C1B—C6B—C5B179.5 (4)
C1A—C6A—C7A—C8A0.3 (6)C4B—C5B—C6B—C7B177.4 (5)
C6A—C7A—C8A—C9A1.1 (7)C4B—C5B—C6B—C1B−1.1 (7)
C1A—N1A—C9A—C10A173.3 (4)C1B—C6B—C7B—C8B0.3 (7)
C22A—N1A—C9A—C10A−8.0 (6)C5B—C6B—C7B—C8B−178.3 (4)
C1A—N1A—C9A—C8A−3.6 (6)C6B—C7B—C8B—C9B−0.6 (7)
C22A—N1A—C9A—C8A175.2 (4)C1B—N1B—C9B—C10B−173.2 (4)
C7A—C8A—C9A—N1A0.4 (6)C22B—N1B—C9B—C10B7.3 (6)
C7A—C8A—C9A—C10A−176.5 (4)C1B—N1B—C9B—C8B1.5 (6)
N1A—C9A—C10A—C11A179.4 (4)C22B—N1B—C9B—C8B−178.0 (4)
C8A—C9A—C10A—C11A−3.8 (6)C7B—C8B—C9B—N1B−0.3 (7)
C9A—C10A—C11A—C12A174.6 (4)C7B—C8B—C9B—C10B174.5 (4)
C10A—C11A—C12A—C13A−173.0 (4)N1B—C9B—C10B—C11B175.8 (4)
C10A—C11A—C12A—C17A5.6 (7)C8B—C9B—C10B—C11B1.3 (7)
C17A—C12A—C13A—C14A−0.7 (6)C9B—C10B—C11B—C12B−172.5 (4)
C11A—C12A—C13A—C14A178.0 (4)C10B—C11B—C12B—C17B−4.1 (8)
C12A—C13A—C14A—C15A1.7 (7)C10B—C11B—C12B—C13B173.9 (5)
C18A—N2A—C15A—C14A−178.5 (5)C17B—C12B—C13B—C14B0.7 (7)
C20X—N2A—C15A—C14A−26.7 (11)C11B—C12B—C13B—C14B−177.5 (5)
C20A—N2A—C15A—C14A20.0 (9)C12B—C13B—C14B—C15B0.1 (8)
C18A—N2A—C15A—C16A3.2 (8)C18B—N2B—C15B—C14B−168.8 (7)
C20X—N2A—C15A—C16A154.9 (8)C20B—N2B—C15B—C14B2.7 (9)
C20A—N2A—C15A—C16A−158.4 (6)C18Y—N2B—C15B—C14B148.1 (8)
C13A—C14A—C15A—N2A−179.8 (5)C18B—N2B—C15B—C16B10.1 (11)
C13A—C14A—C15A—C16A−1.3 (7)C20B—N2B—C15B—C16B−178.5 (6)
N2A—C15A—C16A—C17A178.6 (5)C18Y—N2B—C15B—C16B−33.1 (10)
C14A—C15A—C16A—C17A0.1 (7)C13B—C14B—C15B—N2B177.6 (6)
C15A—C16A—C17A—C12A0.8 (7)C13B—C14B—C15B—C16B−1.4 (8)
C13A—C12A—C17A—C16A−0.5 (6)N2B—C15B—C16B—C17B−177.1 (6)
C11A—C12A—C17A—C16A−179.1 (4)C14B—C15B—C16B—C17B1.8 (8)
C15A—N2A—C18A—C19A−84.1 (7)C15B—C16B—C17B—C12B−1.1 (8)
C20X—N2A—C18A—C19A121.6 (8)C13B—C12B—C17B—C16B−0.2 (7)
C20A—N2A—C18A—C19A78.1 (7)C11B—C12B—C17B—C16B177.9 (5)
C15A—N2A—C20A—C21A−96.3 (8)C15B—N2B—C18B—C19B−83.7 (10)
C18A—N2A—C20A—C21A100.9 (7)C20B—N2B—C18B—C19B104.4 (8)
C20X—N2A—C20A—C21A8.0 (10)C18Y—N2B—C18B—C19B8.6 (14)
C15A—N2A—C20X—C21X100.0 (11)C15B—N2B—C18Y—C19Y112.6 (10)
C18A—N2A—C20X—C21X−105.4 (10)C18B—N2B—C18Y—C19Y3.8 (8)
C20A—N2A—C20X—C21X−0.3 (10)C20B—N2B—C18Y—C19Y−98.9 (10)
C28B—C23B—C24B—C25B−0.8 (6)C15B—N2B—C20B—C21B79.0 (8)
Cl1B—C23B—C24B—C25B179.3 (3)C18B—N2B—C20B—C21B−109.2 (7)
C23B—C24B—C25B—C26B0.1 (6)C18Y—N2B—C20B—C21B−66.9 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1WB—H1WB···O1Bi0.852.362.815 (7)114
O1WB—H2WB···O2Bii0.832.122.953 (7)177
O1WA—H1WA···O2Aiii0.842.072.891 (5)166
O1WA—H2WA···O1A0.762.102.844 (4)169
C8A—H8AA···O3Aiv0.932.543.146 (5)123
C2B—H2BA···O3Bv0.932.573.314 (7)137
C11B—H11B···O1Bvi0.932.413.237 (6)148
C18Y—H18E···Cl1Avii0.972.723.673 (19)169
C19B—H19D···Cl1Bviii0.962.733.531 (14)142
C22B—H22D···O2Bviii0.962.553.259 (7)131
C25A—H25A···O3Aii0.932.563.359 (5)144
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z; (v) x+1, y, z+1; (vi) x+1, −y+3/2, z+1/2; (vii) −x+1, −y, −z+1; (viii) −x+1, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1WB—H1WB···O1Bi0.852.362.815 (7)114
O1WB—H2WB···O2Bii0.832.122.953 (7)177
O1WA—H1WA···O2Aiii0.842.072.891 (5)166
O1WA—H2WA···O1A0.762.102.844 (4)169
C8A—H8AA···O3Aiv0.932.543.146 (5)123
C2B—H2BA···O3Bv0.932.573.314 (7)137
C11B—H11B···O1Bvi0.932.413.237 (6)148
C18Y—H18E···Cl1Avii0.972.723.673 (19)169
C19B—H19D···Cl1Bviii0.962.733.531 (14)142
C22B—H22D···O2Bviii0.962.553.259 (7)131
C25A—H25A···O3Aii0.932.563.359 (5)144
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z; (v) x+1, y, z+1; (vi) x+1, −y+3/2, z+1/2; (vii) −x+1, −y, −z+1; (viii) −x+1, y−1/2, −z+3/2.
 

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Prince of Songkla University for a research grant. An anti­bacterial assay by Dr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is gratefully acknowledged. The authors extend their appreciation to the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

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–S19.  CrossRef Web of Science Google Scholar
 First citationBarchéchath, S. D., Tawatao, R. I., Corr, M., Carson, D. A. & Cottam, H. B. (2005). Bioorg. Med. Chem. Lett. 15, 1785–1788.  Web of Science PubMed Google Scholar
 First citationBolden, S. Jr, Zhu, X. Y., Etukala, J. R., Boateng, C., Mazu, T., Flores-Rozas, H., Jacob, M. R., Khan, S. I., Walker, L. A. & Ablordeppey, S. Y. (2013). Eur. J. Med. Chem. 70, 130–142.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChanawanno, K., Chantrapromma, S., Anantapong, T. & Kanjana-Opas, A. (2010a). Lat. Am. J. Pharm. 29, 1166–1170.  CAS Google Scholar
 First citationChanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010b). Eur. J. Med. Chem. 45, 4199–4208.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationChantrapromma, S., Kaewmanee, N., Boonnak, N., Anantapong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o2728–o2729.  CSD CrossRef CAS IUCr Journals 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 citationFun, H.-K., Kaewmanee, N., Chanawanno, K., Boonnak, N. & Chantrapromma, S. (2013). Acta Cryst. E69, o1510–o1511.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationFun, H.-K., Kaewmanee, N., Chanawanno, K. & Chantrapromma, S. (2011). Acta Cryst. E67, o593–o594.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationKaewmanee, N., Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o2639–o2640.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS 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 citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 4| April 2014| Pages o395-o396
doi:10.1107/S1600536814004577
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS