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

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ISSN: 2056-9890

Di-n-butyl­ammonium 2-(3,5-di-tert-butyl-4-hy­droxy­benzyl­sulfan­yl)nicotinate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 11 August 2008; accepted 13 August 2008; online 20 August 2008)

The asymmetric unit of the title compound, C8H20N+·C21H26NO3S, contains two indpendent ion pairs which are disposed about a psuedo-inversion center, generating an ammonium–carboxylate N—H⋯O hydrogen-bonded four-component cluster. In the crystal structure, adjacent clusters are linked by hydr­oxy–carboxylate O—H⋯O hydrogen bonds, forming a chain.

Related literature

For the applications of hindered phenol-based anti­oxidants, see: Kim & Lee (2003[Kim, T. H. & Lee, N. (2003). Bull. Kor. Chem. Soc., 24, 1809-1813.]); Um et al. (2005[Um, S.-I., Kang, Y.-H. & Lee, J.-Y. (2005). Dyes Pigm. 64, 93-99.]).

[Scheme 1]

Experimental

Crystal data
  • C8H20N+·C21H26NO3S

  • Mr = 502.74

  • Orthorhombic, P c a 21

  • a = 23.4451 (3) Å

  • b = 18.7712 (3) Å

  • c = 12.9657 (2) Å

  • V = 5706.11 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.14 mm−1

  • T = 293 (2) K

  • 0.25 × 0.15 × 0.05 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.965, Tmax = 0.993

  • 53030 measured reflections

  • 13074 independent reflections

  • 10355 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.110

  • S = 1.07

  • 13074 reflections

  • 647 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.32 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 6221 Friedel pairs

  • Flack parameter: 0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H32⋯O2 0.88 1.95 2.826 (2) 172
N3—H31⋯O5 0.88 1.99 2.820 (3) 157
N4—H42⋯O2 0.88 1.97 2.816 (3) 160
N4—H41⋯O5 0.88 1.96 2.834 (2) 172
O3—H3o⋯O1i 0.84 2.04 2.708 (3) 135
O6—H6o⋯O4ii 0.84 1.81 2.651 (3) 175
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

The di-n-butylammonium salt of the substituted nicotinic acid (Scheme I, Fig. 1) is the precursor for the synthesis of hindered phenol-based antioxidants. Phenol-based antioxidants and their derivative have applications in industries such as pharmaceutical, textiles, plastics, polymers, oils, pesticides,dyestuffs, explosives, fluorescent-brightening industries. The salt was isolated along with the expected acid.

Related literature top

For the applications of hindered phenol-based antioxidants, see: Kim & Lee (2003); Um et al. (2005).

Experimental top

2-Mercaptonicotinic acid (1.50 g, 1 mmol), 2,6-di-t-butylphenol (2.00 g, 1 mmol) and paraformaldehyde (0.291 g,1 mmol) were intimately grounded and to the powder was added di-n-butylamine (0.09 ml). The slurry was heated to 373–383 K. The slurry solidified after an hour. The solid was purified by column chromatography, with chloroform as solvent, to give two products, one of which was 2-(3,5-di-t-butyl-4-hydroxybenzylthio)nicotinic acid and the other, di-n-butylammonium salt of the acid.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The acid H-atom was located in a difference Fourier map, and was refined with a distance restraint of O–H 0.84±0.01 Å; its temperature factors were freely refined. The hydroxy H-atom was placed in a chemically sensible position, with a distance of more than 2 Å from the neighboring methyl H-atoms. The C–O–H fragment is then perpendicular to the aromatic ring.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of O–H···O hydrogen-bonded dimeric structure of [(C4H9)2NH2] [C21H26NO3S] at the 70% probability level. Dashed lines denote the intra-ionic hydrogen bonds in the salt. Hydrogen atoms are drawn as spheres of arbitrary radius.
Di-n-butylammonium 2-(3,5-di-tert-butyl-4-hydroxybenzylsulfanyl)nicotinate top
Crystal data top
C8H20N+·C21H26NO3SF(000) = 2192
Mr = 502.74Dx = 1.170 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6621 reflections
a = 23.4451 (3) Åθ = 2.2–25.1°
b = 18.7712 (3) ŵ = 0.15 mm1
c = 12.9657 (2) ÅT = 293 K
V = 5706.11 (15) Å3Prism, colorless
Z = 80.25 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer
13074 independent reflections
Radiation source: fine-focus sealed tube10355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3030
Tmin = 0.965, Tmax = 0.993k = 2424
53030 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.047P)2 + 0.106P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
13074 reflectionsΔρmax = 0.37 e Å3
647 parametersΔρmin = 0.32 e Å3
1 restraintAbsolute structure: Flack (1983), 6221 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (6)
Crystal data top
C8H20N+·C21H26NO3SV = 5706.11 (15) Å3
Mr = 502.74Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 23.4451 (3) ŵ = 0.15 mm1
b = 18.7712 (3) ÅT = 293 K
c = 12.9657 (2) Å0.25 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer
13074 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
10355 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.993Rint = 0.066
53030 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.37 e Å3
S = 1.07Δρmin = 0.32 e Å3
13074 reflectionsAbsolute structure: Flack (1983), 6221 Friedel pairs
647 parametersAbsolute structure parameter: 0.03 (6)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.61020 (3)0.10851 (3)0.49998 (5)0.01813 (13)
S20.37510 (2)0.39163 (3)0.74680 (5)0.01700 (13)
O10.55912 (8)0.15648 (10)0.82414 (14)0.0307 (5)
O20.54769 (7)0.17288 (9)0.65688 (14)0.0215 (4)
O30.59777 (7)0.18381 (9)0.01696 (14)0.0275 (4)
H3O0.60430.16690.04180.041*
O40.41450 (9)0.34101 (11)0.41905 (14)0.0367 (5)
O50.43445 (7)0.32878 (9)0.58473 (13)0.0206 (4)
O60.41772 (7)0.31263 (8)1.21888 (13)0.0190 (4)
H6O0.41540.32381.28150.028*
N10.68358 (9)0.02784 (11)0.60001 (18)0.0216 (5)
N20.30600 (9)0.48203 (10)0.65446 (18)0.0202 (5)
N30.48194 (8)0.27324 (10)0.76764 (15)0.0171 (4)
H310.46210.29820.72280.021*
H320.49940.23900.73380.021*
N40.50031 (8)0.22795 (10)0.47395 (16)0.0183 (5)
H410.48170.26240.50530.022*
H420.52050.20520.52070.022*
C10.57288 (10)0.14489 (12)0.7329 (2)0.0174 (5)
C20.62184 (10)0.09532 (12)0.7132 (2)0.0154 (5)
C30.65056 (10)0.06652 (12)0.7969 (2)0.0183 (5)
H30.63930.07900.86490.022*
C40.69525 (10)0.02001 (13)0.7826 (2)0.0241 (6)
H40.71550.00100.83980.029*
C50.70982 (11)0.00190 (14)0.6839 (2)0.0261 (6)
H50.74020.03090.67420.031*
C60.64087 (10)0.07440 (12)0.6142 (2)0.0168 (5)
C70.64989 (12)0.05976 (14)0.4028 (2)0.0224 (6)
H7A0.69130.06370.41630.027*
H7B0.63930.00870.40460.027*
C80.63593 (10)0.09092 (12)0.2985 (2)0.0171 (5)
C90.67319 (10)0.13750 (12)0.2502 (2)0.0195 (5)
H90.70800.14920.28360.023*
C100.66148 (10)0.16767 (12)0.1548 (2)0.0174 (5)
C110.60902 (10)0.15045 (13)0.1087 (2)0.0167 (5)
C120.56896 (10)0.10404 (12)0.1557 (2)0.0149 (5)
C130.58492 (10)0.07448 (12)0.2512 (2)0.0178 (5)
H130.55970.04210.28420.021*
C140.70550 (10)0.21645 (13)0.1011 (2)0.0189 (5)
C150.75874 (11)0.22665 (13)0.1683 (2)0.0273 (6)
H15A0.78610.25720.13220.041*
H15B0.77630.18020.18210.041*
H15C0.74790.24910.23370.041*
C160.72503 (11)0.18201 (13)0.0005 (2)0.0269 (6)
H16A0.75710.20910.02890.040*
H16B0.69340.18220.04990.040*
H16C0.73700.13280.01270.040*
C170.68062 (11)0.29091 (12)0.0801 (2)0.0231 (6)
H17A0.70890.31990.04340.035*
H17B0.67100.31390.14570.035*
H17C0.64620.28640.03780.035*
C180.50986 (10)0.08924 (13)0.1108 (2)0.0195 (5)
C190.51350 (11)0.04930 (14)0.0071 (2)0.0269 (6)
H19A0.53300.07930.04380.040*
H19B0.47490.03830.01730.040*
H19C0.53490.00490.01650.040*
C200.47803 (11)0.16037 (14)0.0993 (2)0.0269 (6)
H20A0.50000.19230.05460.040*
H20B0.47330.18240.16730.040*
H20C0.44040.15180.06860.040*
C210.47340 (11)0.04226 (15)0.1813 (2)0.0304 (7)
H21A0.49130.00470.18830.046*
H21B0.43530.03680.15130.046*
H21C0.47020.06460.24930.046*
C220.40686 (10)0.35717 (12)0.5114 (2)0.0181 (5)
C230.36259 (10)0.41265 (12)0.53553 (19)0.0143 (5)
C240.33721 (10)0.44858 (12)0.4542 (2)0.0184 (5)
H240.34800.43740.38540.022*
C250.29663 (10)0.50023 (13)0.4717 (2)0.0208 (6)
H250.27900.52500.41620.025*
C260.28250 (11)0.51463 (13)0.5729 (2)0.0225 (6)
H260.25430.54990.58560.027*
C270.34564 (10)0.43232 (12)0.63614 (19)0.0141 (5)
C280.33757 (11)0.43887 (13)0.8492 (2)0.0170 (5)
H28A0.34630.49040.84610.020*
H28B0.29590.43250.84160.020*
C290.35749 (10)0.40803 (12)0.95089 (19)0.0148 (5)
C300.32436 (10)0.35929 (12)1.0027 (2)0.0173 (5)
H300.28840.34640.97460.021*
C310.34198 (10)0.32795 (12)1.0958 (2)0.0155 (5)
C320.39612 (10)0.34766 (12)1.13377 (19)0.0157 (5)
C330.43076 (10)0.39769 (12)1.08274 (19)0.0146 (5)
C340.40991 (10)0.42713 (12)0.9921 (2)0.0162 (5)
H340.43230.46160.95700.019*
C350.30171 (10)0.27660 (12)1.1540 (2)0.0183 (5)
C360.24629 (11)0.26426 (13)1.0958 (2)0.0243 (6)
H36A0.25460.24251.02870.036*
H36B0.22690.30991.08520.036*
H36C0.22170.23241.13580.036*
C370.28590 (11)0.31062 (13)1.2593 (2)0.0241 (6)
H37A0.27110.35881.24810.036*
H37B0.31990.31301.30310.036*
H37C0.25670.28161.29330.036*
C380.32972 (11)0.20349 (12)1.1719 (2)0.0216 (6)
H38A0.33750.18081.10530.032*
H38B0.30390.17331.21230.032*
H38C0.36560.20981.20960.032*
C390.48994 (11)0.41931 (13)1.1241 (2)0.0196 (5)
C400.48624 (11)0.44881 (13)1.2354 (2)0.0251 (6)
H40A0.47450.41061.28240.038*
H40B0.45820.48751.23790.038*
H40C0.52370.46701.25640.038*
C410.53056 (11)0.35538 (14)1.1212 (2)0.0261 (6)
H41A0.53310.33721.05050.039*
H41B0.51610.31781.16670.039*
H41C0.56850.37021.14460.039*
C420.51695 (12)0.47812 (15)1.0582 (2)0.0322 (7)
H42A0.52060.46150.98690.048*
H42B0.55480.48981.08560.048*
H42C0.49270.52061.06010.048*
C430.65576 (12)0.42326 (16)0.7114 (2)0.0344 (7)
H43A0.68510.45080.74760.052*
H43B0.63440.45470.66500.052*
H43C0.67390.38530.67130.052*
C440.61514 (10)0.39058 (14)0.7898 (2)0.0253 (6)
H44A0.63690.35870.83630.030*
H44B0.59820.42900.83220.030*
C450.56770 (11)0.34850 (13)0.7389 (2)0.0238 (6)
H45A0.54760.37950.68890.029*
H45B0.58440.30810.70020.029*
C460.52529 (10)0.32027 (13)0.8164 (2)0.0199 (5)
H46A0.54590.29320.87030.024*
H46B0.50580.36080.85020.024*
C470.44247 (10)0.24120 (13)0.84408 (19)0.0194 (5)
H47A0.42350.27980.88330.023*
H47B0.46480.21220.89350.023*
C480.39737 (11)0.19470 (13)0.7948 (2)0.0216 (6)
H48A0.41600.15520.75710.026*
H48B0.37530.22320.74440.026*
C490.35703 (11)0.16424 (14)0.8757 (2)0.0251 (6)
H49A0.37940.13430.92390.030*
H49B0.34070.20410.91590.030*
C500.30874 (11)0.12013 (15)0.8326 (3)0.0325 (7)
H50A0.28440.10350.88920.049*
H50B0.32440.07900.79550.049*
H50C0.28610.14920.78510.049*
C510.33482 (13)0.06566 (15)0.5409 (2)0.0332 (7)
H51A0.30610.03590.50680.050*
H51B0.31570.10300.58090.050*
H51C0.35800.03610.58710.050*
C520.37294 (11)0.09964 (14)0.4602 (2)0.0271 (6)
H52A0.34910.12710.41130.033*
H52B0.39260.06170.42080.033*
C530.41734 (10)0.14901 (13)0.5081 (2)0.0218 (6)
H53A0.39780.18940.54220.026*
H53B0.43910.12270.56130.026*
C540.45836 (11)0.17755 (13)0.4273 (2)0.0207 (6)
H54A0.47900.13730.39500.025*
H54B0.43660.20240.37260.025*
C550.53960 (11)0.25952 (13)0.3961 (2)0.0195 (5)
H55A0.51750.28970.34790.023*
H55B0.55770.22090.35570.023*
C560.58557 (11)0.30413 (13)0.44713 (19)0.0209 (6)
H56A0.60580.27510.49940.025*
H56B0.56780.34520.48270.025*
C570.62798 (11)0.33087 (15)0.3670 (2)0.0270 (6)
H57A0.64170.28990.32580.032*
H57B0.60810.36390.31950.032*
C580.67879 (12)0.36869 (14)0.4135 (2)0.0312 (7)
H58A0.70370.38600.35820.047*
H58B0.70000.33550.45740.047*
H58C0.66560.40910.45500.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0223 (3)0.0195 (3)0.0126 (3)0.0055 (2)0.0010 (3)0.0002 (3)
S20.0206 (3)0.0185 (3)0.0120 (3)0.0065 (2)0.0000 (2)0.0012 (3)
O10.0422 (12)0.0361 (11)0.0137 (10)0.0189 (9)0.0019 (9)0.0003 (8)
O20.0245 (10)0.0234 (9)0.0165 (9)0.0082 (7)0.0021 (8)0.0004 (8)
O30.0347 (11)0.0353 (10)0.0124 (10)0.0099 (8)0.0040 (8)0.0088 (8)
O40.0512 (14)0.0457 (12)0.0131 (10)0.0302 (10)0.0003 (9)0.0032 (9)
O50.0263 (10)0.0229 (9)0.0127 (9)0.0090 (7)0.0012 (8)0.0011 (7)
O60.0234 (9)0.0213 (9)0.0122 (9)0.0025 (7)0.0018 (7)0.0033 (7)
N10.0219 (11)0.0222 (11)0.0206 (12)0.0052 (9)0.0005 (9)0.0030 (9)
N20.0218 (11)0.0213 (10)0.0177 (11)0.0056 (8)0.0006 (9)0.0062 (9)
N30.0214 (11)0.0170 (10)0.0130 (11)0.0064 (8)0.0013 (8)0.0009 (8)
N40.0196 (11)0.0193 (10)0.0159 (11)0.0065 (8)0.0018 (9)0.0007 (8)
C10.0208 (13)0.0156 (12)0.0156 (14)0.0008 (9)0.0009 (10)0.0022 (10)
C20.0191 (12)0.0130 (11)0.0142 (13)0.0036 (9)0.0001 (10)0.0004 (9)
C30.0208 (13)0.0189 (12)0.0152 (13)0.0036 (10)0.0007 (10)0.0003 (10)
C40.0211 (14)0.0309 (15)0.0204 (15)0.0030 (11)0.0026 (11)0.0073 (11)
C50.0209 (14)0.0291 (14)0.0283 (17)0.0111 (11)0.0008 (11)0.0074 (12)
C60.0174 (12)0.0154 (11)0.0175 (14)0.0015 (9)0.0025 (10)0.0014 (10)
C70.0264 (14)0.0227 (14)0.0179 (15)0.0064 (11)0.0001 (11)0.0002 (11)
C80.0206 (14)0.0169 (12)0.0139 (14)0.0063 (10)0.0025 (10)0.0022 (10)
C90.0200 (12)0.0201 (12)0.0185 (13)0.0050 (10)0.0025 (11)0.0048 (11)
C100.0175 (12)0.0165 (12)0.0182 (13)0.0013 (9)0.0035 (10)0.0005 (10)
C110.0216 (13)0.0188 (12)0.0098 (13)0.0016 (10)0.0007 (10)0.0001 (10)
C120.0150 (12)0.0152 (12)0.0144 (13)0.0004 (9)0.0007 (10)0.0018 (10)
C130.0216 (13)0.0150 (12)0.0166 (14)0.0013 (9)0.0068 (11)0.0004 (11)
C140.0148 (12)0.0220 (13)0.0200 (14)0.0015 (9)0.0036 (10)0.0002 (11)
C150.0205 (14)0.0315 (14)0.0298 (16)0.0029 (11)0.0008 (12)0.0017 (12)
C160.0268 (14)0.0298 (14)0.0241 (15)0.0038 (11)0.0062 (12)0.0030 (12)
C170.0202 (13)0.0234 (13)0.0257 (15)0.0021 (10)0.0045 (11)0.0019 (11)
C180.0163 (12)0.0237 (13)0.0184 (13)0.0046 (10)0.0012 (10)0.0027 (11)
C190.0294 (15)0.0333 (15)0.0180 (14)0.0087 (12)0.0018 (12)0.0056 (13)
C200.0198 (13)0.0345 (15)0.0264 (15)0.0015 (11)0.0042 (12)0.0039 (12)
C210.0281 (15)0.0381 (16)0.0249 (16)0.0128 (12)0.0018 (12)0.0010 (12)
C220.0220 (13)0.0175 (12)0.0148 (13)0.0010 (10)0.0006 (11)0.0004 (10)
C230.0168 (13)0.0124 (11)0.0139 (13)0.0013 (10)0.0001 (10)0.0001 (9)
C240.0216 (13)0.0203 (13)0.0132 (13)0.0031 (10)0.0004 (10)0.0023 (10)
C250.0211 (13)0.0242 (13)0.0171 (13)0.0011 (10)0.0019 (10)0.0079 (10)
C260.0258 (14)0.0225 (13)0.0192 (14)0.0084 (10)0.0002 (11)0.0026 (10)
C270.0157 (12)0.0128 (11)0.0139 (13)0.0028 (9)0.0015 (10)0.0034 (9)
C280.0193 (13)0.0177 (12)0.0139 (13)0.0059 (10)0.0027 (10)0.0019 (10)
C290.0176 (12)0.0145 (12)0.0124 (13)0.0059 (9)0.0003 (10)0.0026 (10)
C300.0174 (12)0.0178 (12)0.0167 (13)0.0018 (9)0.0012 (10)0.0026 (11)
C310.0173 (12)0.0153 (11)0.0137 (13)0.0028 (9)0.0044 (10)0.0052 (10)
C320.0192 (12)0.0175 (12)0.0106 (13)0.0058 (10)0.0002 (10)0.0011 (10)
C330.0158 (12)0.0146 (12)0.0133 (13)0.0004 (9)0.0016 (9)0.0047 (10)
C340.0194 (12)0.0137 (11)0.0154 (14)0.0013 (9)0.0034 (10)0.0028 (10)
C350.0171 (12)0.0215 (12)0.0164 (13)0.0004 (10)0.0052 (10)0.0003 (11)
C360.0195 (13)0.0252 (13)0.0281 (15)0.0024 (10)0.0015 (12)0.0024 (12)
C370.0230 (13)0.0269 (13)0.0224 (15)0.0029 (10)0.0098 (11)0.0013 (11)
C380.0222 (13)0.0187 (12)0.0238 (15)0.0015 (10)0.0028 (11)0.0023 (11)
C390.0210 (13)0.0217 (13)0.0160 (14)0.0046 (10)0.0008 (10)0.0002 (10)
C400.0291 (14)0.0243 (13)0.0220 (16)0.0041 (11)0.0052 (12)0.0044 (12)
C410.0188 (13)0.0399 (15)0.0197 (14)0.0019 (11)0.0016 (11)0.0036 (12)
C420.0297 (16)0.0395 (17)0.0275 (16)0.0155 (13)0.0038 (12)0.0044 (13)
C430.0311 (16)0.0406 (17)0.0315 (17)0.0076 (13)0.0051 (13)0.0065 (13)
C440.0255 (15)0.0316 (15)0.0187 (15)0.0001 (11)0.0000 (11)0.0001 (12)
C450.0285 (14)0.0231 (13)0.0197 (15)0.0007 (10)0.0001 (12)0.0003 (11)
C460.0249 (14)0.0212 (13)0.0135 (13)0.0030 (10)0.0016 (11)0.0032 (10)
C470.0218 (13)0.0247 (13)0.0116 (13)0.0021 (11)0.0008 (10)0.0016 (10)
C480.0249 (14)0.0202 (13)0.0197 (15)0.0018 (11)0.0014 (11)0.0025 (11)
C490.0267 (15)0.0246 (14)0.0241 (16)0.0013 (11)0.0000 (12)0.0015 (12)
C500.0300 (16)0.0292 (15)0.0385 (19)0.0023 (12)0.0103 (14)0.0085 (13)
C510.0353 (17)0.0401 (17)0.0242 (16)0.0098 (13)0.0034 (13)0.0026 (13)
C520.0275 (15)0.0317 (15)0.0223 (16)0.0045 (11)0.0012 (12)0.0022 (12)
C530.0280 (14)0.0218 (13)0.0156 (13)0.0009 (10)0.0029 (11)0.0013 (11)
C540.0227 (14)0.0233 (13)0.0160 (13)0.0022 (10)0.0025 (10)0.0009 (11)
C550.0225 (14)0.0205 (13)0.0156 (13)0.0037 (10)0.0022 (10)0.0002 (10)
C560.0259 (14)0.0225 (13)0.0144 (14)0.0022 (10)0.0009 (11)0.0001 (10)
C570.0278 (15)0.0309 (15)0.0222 (15)0.0033 (12)0.0014 (12)0.0009 (12)
C580.0300 (16)0.0272 (14)0.0363 (18)0.0040 (12)0.0098 (13)0.0063 (13)
Geometric parameters (Å, º) top
S1—C61.767 (3)C29—C341.388 (3)
S1—C71.814 (3)C30—C311.405 (4)
S2—C271.766 (2)C30—H300.9500
S2—C281.823 (2)C31—C321.411 (3)
O1—C11.245 (3)C31—C351.546 (3)
O2—C11.264 (3)C32—C331.407 (3)
O3—C111.370 (3)C33—C341.387 (3)
O3—H3O0.8400C33—C391.542 (3)
O4—C221.248 (3)C34—H340.9500
O5—C221.268 (3)C35—C361.521 (4)
O6—C321.381 (3)C35—C381.539 (3)
O6—H6O0.8400C35—C371.552 (4)
N1—C61.342 (3)C36—H36A0.9800
N1—C51.341 (3)C36—H36B0.9800
N2—C261.340 (3)C36—H36C0.9800
N2—C271.338 (3)C37—H37A0.9800
N3—C471.483 (3)C37—H37B0.9800
N3—C461.487 (3)C37—H37C0.9800
N3—H310.8800C38—H38A0.9800
N3—H320.8800C38—H38B0.9800
N4—C551.490 (3)C38—H38C0.9800
N4—C541.493 (3)C39—C421.533 (4)
N4—H410.8800C39—C411.533 (3)
N4—H420.8800C39—C401.548 (4)
C1—C21.500 (3)C40—H40A0.9800
C2—C31.387 (3)C40—H40B0.9800
C2—C61.415 (4)C40—H40C0.9800
C3—C41.377 (3)C41—H41A0.9800
C3—H30.9500C41—H41B0.9800
C4—C51.367 (4)C41—H41C0.9800
C4—H40.9500C42—H42A0.9800
C5—H50.9500C42—H42B0.9800
C7—C81.509 (4)C42—H42C0.9800
C7—H7A0.9900C43—C441.521 (4)
C7—H7B0.9900C43—H43A0.9800
C8—C131.379 (3)C43—H43B0.9800
C8—C91.385 (3)C43—H43C0.9800
C9—C101.388 (4)C44—C451.515 (4)
C9—H90.9500C44—H44A0.9900
C10—C111.405 (3)C44—H44B0.9900
C10—C141.546 (3)C45—C461.510 (4)
C11—C121.419 (3)C45—H45A0.9900
C12—C131.408 (4)C45—H45B0.9900
C12—C181.528 (3)C46—H46A0.9900
C13—H130.9500C46—H46B0.9900
C14—C151.535 (4)C47—C481.513 (3)
C14—C161.536 (4)C47—H47A0.9900
C14—C171.539 (3)C47—H47B0.9900
C15—H15A0.9800C48—C491.524 (4)
C15—H15B0.9800C48—H48A0.9900
C15—H15C0.9800C48—H48B0.9900
C16—H16A0.9800C49—C501.510 (4)
C16—H16B0.9800C49—H49A0.9900
C16—H16C0.9800C49—H49B0.9900
C17—H17A0.9800C50—H50A0.9800
C17—H17B0.9800C50—H50B0.9800
C17—H17C0.9800C50—H50C0.9800
C18—C211.531 (4)C51—C521.517 (4)
C18—C201.537 (3)C51—H51A0.9800
C18—C191.541 (4)C51—H51B0.9800
C19—H19A0.9800C51—H51C0.9800
C19—H19B0.9800C52—C531.525 (3)
C19—H19C0.9800C52—H52A0.9900
C20—H20A0.9800C52—H52B0.9900
C20—H20B0.9800C53—C541.519 (4)
C20—H20C0.9800C53—H53A0.9900
C21—H21A0.9800C53—H53B0.9900
C21—H21B0.9800C54—H54A0.9900
C21—H21C0.9800C54—H54B0.9900
C22—C231.503 (3)C55—C561.517 (3)
C23—C241.386 (3)C55—H55A0.9900
C23—C271.413 (3)C55—H55B0.9900
C24—C251.377 (3)C56—C571.523 (4)
C24—H240.9500C56—H56A0.9900
C25—C261.381 (4)C56—H56B0.9900
C25—H250.9500C57—C581.512 (4)
C26—H260.9500C57—H57A0.9900
C28—C291.514 (4)C57—H57B0.9900
C28—H28A0.9900C58—H58A0.9800
C28—H28B0.9900C58—H58B0.9800
C29—C301.375 (3)C58—H58C0.9800
C6—S1—C7101.00 (12)C29—C34—C33122.4 (2)
C27—S2—C28101.10 (11)C29—C34—H34118.8
C11—O3—H3O125.4C33—C34—H34118.8
C32—O6—H6O129.0C36—C35—C38107.7 (2)
C6—N1—C5117.9 (2)C36—C35—C31112.0 (2)
C26—N2—C27117.7 (2)C38—C35—C31111.66 (19)
C47—N3—C46112.50 (19)C36—C35—C37107.2 (2)
C47—N3—H31109.1C38—C35—C37109.6 (2)
C46—N3—H31109.1C31—C35—C37108.57 (19)
C47—N3—H32109.1C35—C36—H36A109.5
C46—N3—H32109.1C35—C36—H36B109.5
H31—N3—H32107.8H36A—C36—H36B109.5
C55—N4—C54112.64 (19)C35—C36—H36C109.5
C55—N4—H41109.1H36A—C36—H36C109.5
C54—N4—H41109.1H36B—C36—H36C109.5
C55—N4—H42109.1C35—C37—H37A109.5
C54—N4—H42109.1C35—C37—H37B109.5
H41—N4—H42107.8H37A—C37—H37B109.5
O1—C1—O2123.2 (2)C35—C37—H37C109.5
O1—C1—C2117.9 (2)H37A—C37—H37C109.5
O2—C1—C2118.9 (2)H37B—C37—H37C109.5
C3—C2—C6116.7 (2)C35—C38—H38A109.5
C3—C2—C1118.7 (2)C35—C38—H38B109.5
C6—C2—C1124.6 (2)H38A—C38—H38B109.5
C4—C3—C2120.7 (2)C35—C38—H38C109.5
C4—C3—H3119.6H38A—C38—H38C109.5
C2—C3—H3119.6H38B—C38—H38C109.5
C5—C4—C3118.3 (2)C42—C39—C41107.1 (2)
C5—C4—H4120.8C42—C39—C33111.6 (2)
C3—C4—H4120.8C41—C39—C33110.2 (2)
N1—C5—C4123.6 (2)C42—C39—C40106.6 (2)
N1—C5—H5118.2C41—C39—C40109.7 (2)
C4—C5—H5118.2C33—C39—C40111.6 (2)
N1—C6—C2122.7 (2)C39—C40—H40A109.5
N1—C6—S1115.14 (19)C39—C40—H40B109.5
C2—C6—S1122.13 (18)H40A—C40—H40B109.5
C8—C7—S1108.40 (17)C39—C40—H40C109.5
C8—C7—H7A110.0H40A—C40—H40C109.5
S1—C7—H7A110.0H40B—C40—H40C109.5
C8—C7—H7B110.0C39—C41—H41A109.5
S1—C7—H7B110.0C39—C41—H41B109.5
H7A—C7—H7B108.4H41A—C41—H41B109.5
C13—C8—C9119.1 (2)C39—C41—H41C109.5
C13—C8—C7120.0 (2)H41A—C41—H41C109.5
C9—C8—C7120.8 (2)H41B—C41—H41C109.5
C8—C9—C10122.4 (2)C39—C42—H42A109.5
C8—C9—H9118.8C39—C42—H42B109.5
C10—C9—H9118.8H42A—C42—H42B109.5
C9—C10—C11117.3 (2)C39—C42—H42C109.5
C9—C10—C14120.8 (2)H42A—C42—H42C109.5
C11—C10—C14121.9 (2)H42B—C42—H42C109.5
O3—C11—C10115.6 (2)C44—C43—H43A109.5
O3—C11—C12121.7 (2)C44—C43—H43B109.5
C10—C11—C12122.6 (2)H43A—C43—H43B109.5
C13—C12—C11116.3 (2)C44—C43—H43C109.5
C13—C12—C18120.3 (2)H43A—C43—H43C109.5
C11—C12—C18123.3 (2)H43B—C43—H43C109.5
C8—C13—C12122.2 (2)C45—C44—C43112.3 (2)
C8—C13—H13118.9C45—C44—H44A109.2
C12—C13—H13118.9C43—C44—H44A109.2
C15—C14—C16107.3 (2)C45—C44—H44B109.2
C15—C14—C17107.2 (2)C43—C44—H44B109.2
C16—C14—C17110.1 (2)H44A—C44—H44B107.9
C15—C14—C10111.1 (2)C46—C45—C44112.1 (2)
C16—C14—C10109.6 (2)C46—C45—H45A109.2
C17—C14—C10111.39 (19)C44—C45—H45A109.2
C14—C15—H15A109.5C46—C45—H45B109.2
C14—C15—H15B109.5C44—C45—H45B109.2
H15A—C15—H15B109.5H45A—C45—H45B107.9
C14—C15—H15C109.5N3—C46—C45112.0 (2)
H15A—C15—H15C109.5N3—C46—H46A109.2
H15B—C15—H15C109.5C45—C46—H46A109.2
C14—C16—H16A109.5N3—C46—H46B109.2
C14—C16—H16B109.5C45—C46—H46B109.2
H16A—C16—H16B109.5H46A—C46—H46B107.9
C14—C16—H16C109.5N3—C47—C48112.8 (2)
H16A—C16—H16C109.5N3—C47—H47A109.0
H16B—C16—H16C109.5C48—C47—H47A109.0
C14—C17—H17A109.5N3—C47—H47B109.0
C14—C17—H17B109.5C48—C47—H47B109.0
H17A—C17—H17B109.5H47A—C47—H47B107.8
C14—C17—H17C109.5C47—C48—C49111.1 (2)
H17A—C17—H17C109.5C47—C48—H48A109.4
H17B—C17—H17C109.5C49—C48—H48A109.4
C12—C18—C21112.5 (2)C47—C48—H48B109.4
C12—C18—C20108.62 (19)C49—C48—H48B109.4
C21—C18—C20106.7 (2)H48A—C48—H48B108.0
C12—C18—C19111.7 (2)C50—C49—C48114.6 (2)
C21—C18—C19105.8 (2)C50—C49—H49A108.6
C20—C18—C19111.4 (2)C48—C49—H49A108.6
C18—C19—H19A109.5C50—C49—H49B108.6
C18—C19—H19B109.5C48—C49—H49B108.6
H19A—C19—H19B109.5H49A—C49—H49B107.6
C18—C19—H19C109.5C49—C50—H50A109.5
H19A—C19—H19C109.5C49—C50—H50B109.5
H19B—C19—H19C109.5H50A—C50—H50B109.5
C18—C20—H20A109.5C49—C50—H50C109.5
C18—C20—H20B109.5H50A—C50—H50C109.5
H20A—C20—H20B109.5H50B—C50—H50C109.5
C18—C20—H20C109.5C52—C51—H51A109.5
H20A—C20—H20C109.5C52—C51—H51B109.5
H20B—C20—H20C109.5H51A—C51—H51B109.5
C18—C21—H21A109.5C52—C51—H51C109.5
C18—C21—H21B109.5H51A—C51—H51C109.5
H21A—C21—H21B109.5H51B—C51—H51C109.5
C18—C21—H21C109.5C51—C52—C53112.2 (2)
H21A—C21—H21C109.5C51—C52—H52A109.2
H21B—C21—H21C109.5C53—C52—H52A109.2
O4—C22—O5123.0 (2)C51—C52—H52B109.2
O4—C22—C23117.9 (2)C53—C52—H52B109.2
O5—C22—C23119.1 (2)H52A—C52—H52B107.9
C24—C23—C27117.0 (2)C54—C53—C52111.5 (2)
C24—C23—C22118.4 (2)C54—C53—H53A109.3
C27—C23—C22124.6 (2)C52—C53—H53A109.3
C25—C24—C23120.9 (2)C54—C53—H53B109.3
C25—C24—H24119.5C52—C53—H53B109.3
C23—C24—H24119.5H53A—C53—H53B108.0
C26—C25—C24117.4 (2)N4—C54—C53111.2 (2)
C26—C25—H25121.3N4—C54—H54A109.4
C24—C25—H25121.3C53—C54—H54A109.4
N2—C26—C25124.2 (2)N4—C54—H54B109.4
N2—C26—H26117.9C53—C54—H54B109.4
C25—C26—H26117.9H54A—C54—H54B108.0
N2—C27—C23122.8 (2)N4—C55—C56111.3 (2)
N2—C27—S2115.40 (19)N4—C55—H55A109.4
C23—C27—S2121.81 (18)C56—C55—H55A109.4
C29—C28—S2107.43 (16)N4—C55—H55B109.4
C29—C28—H28A110.2C56—C55—H55B109.4
S2—C28—H28A110.2H55A—C55—H55B108.0
C29—C28—H28B110.2C55—C56—C57110.4 (2)
S2—C28—H28B110.2C55—C56—H56A109.6
H28A—C28—H28B108.5C57—C56—H56A109.6
C30—C29—C34118.9 (2)C55—C56—H56B109.6
C30—C29—C28120.4 (2)C57—C56—H56B109.6
C34—C29—C28120.7 (2)H56A—C56—H56B108.1
C29—C30—C31122.2 (2)C58—C57—C56113.4 (2)
C29—C30—H30118.9C58—C57—H57A108.9
C31—C30—H30118.9C56—C57—H57A108.9
C30—C31—C32117.0 (2)C58—C57—H57B108.9
C30—C31—C35120.0 (2)C56—C57—H57B108.9
C32—C31—C35122.9 (2)H57A—C57—H57B107.7
O6—C32—C33118.8 (2)C57—C58—H58A109.5
O6—C32—C31118.9 (2)C57—C58—H58B109.5
C33—C32—C31122.0 (2)H58A—C58—H58B109.5
C34—C33—C32117.4 (2)C57—C58—H58C109.5
C34—C33—C39120.4 (2)H58A—C58—H58C109.5
C32—C33—C39122.1 (2)H58B—C58—H58C109.5
O1—C1—C2—C32.0 (3)C23—C24—C25—C260.1 (4)
O2—C1—C2—C3177.9 (2)C27—N2—C26—C250.1 (4)
O1—C1—C2—C6177.0 (2)C24—C25—C26—N20.5 (4)
O2—C1—C2—C63.1 (4)C26—N2—C27—C231.0 (4)
C6—C2—C3—C40.0 (3)C26—N2—C27—S2179.77 (18)
C1—C2—C3—C4179.1 (2)C24—C23—C27—N21.5 (3)
C2—C3—C4—C51.3 (4)C22—C23—C27—N2180.0 (2)
C6—N1—C5—C40.4 (4)C24—C23—C27—S2179.28 (17)
C3—C4—C5—N11.1 (4)C22—C23—C27—S20.8 (3)
C5—N1—C6—C21.7 (4)C28—S2—C27—N21.2 (2)
C5—N1—C6—S1177.84 (19)C28—S2—C27—C23179.6 (2)
C3—C2—C6—N11.5 (4)C27—S2—C28—C29178.54 (17)
C1—C2—C6—N1177.5 (2)S2—C28—C29—C30100.7 (2)
C3—C2—C6—S1177.98 (18)S2—C28—C29—C3477.8 (2)
C1—C2—C6—S13.0 (3)C34—C29—C30—C310.3 (4)
C7—S1—C6—N12.7 (2)C28—C29—C30—C31178.2 (2)
C7—S1—C6—C2177.7 (2)C29—C30—C31—C321.1 (3)
C6—S1—C7—C8170.89 (18)C29—C30—C31—C35176.7 (2)
S1—C7—C8—C1377.3 (3)C30—C31—C32—O6173.2 (2)
S1—C7—C8—C9101.1 (2)C35—C31—C32—O69.1 (3)
C13—C8—C9—C100.9 (4)C30—C31—C32—C331.5 (3)
C7—C8—C9—C10179.4 (2)C35—C31—C32—C33176.2 (2)
C8—C9—C10—C111.4 (4)O6—C32—C33—C34174.2 (2)
C8—C9—C10—C14176.9 (2)C31—C32—C33—C340.5 (3)
C9—C10—C11—O3177.0 (2)O6—C32—C33—C395.3 (3)
C14—C10—C11—O34.6 (3)C31—C32—C33—C39180.0 (2)
C9—C10—C11—C120.3 (4)C30—C29—C34—C331.4 (4)
C14—C10—C11—C12178.0 (2)C28—C29—C34—C33177.1 (2)
O3—C11—C12—C13178.4 (2)C32—C33—C34—C291.0 (3)
C10—C11—C12—C131.2 (3)C39—C33—C34—C29178.5 (2)
O3—C11—C12—C182.1 (4)C30—C31—C35—C362.6 (3)
C10—C11—C12—C18175.1 (2)C32—C31—C35—C36179.8 (2)
C9—C8—C13—C120.7 (4)C30—C31—C35—C38123.5 (2)
C7—C8—C13—C12177.7 (2)C32—C31—C35—C3858.9 (3)
C11—C12—C13—C81.7 (3)C30—C31—C35—C37115.6 (2)
C18—C12—C13—C8174.7 (2)C32—C31—C35—C3762.1 (3)
C9—C10—C14—C151.9 (3)C34—C33—C39—C424.3 (3)
C11—C10—C14—C15179.8 (2)C32—C33—C39—C42176.2 (2)
C9—C10—C14—C16116.5 (3)C34—C33—C39—C41114.5 (2)
C11—C10—C14—C1661.8 (3)C32—C33—C39—C4165.0 (3)
C9—C10—C14—C17121.4 (3)C34—C33—C39—C40123.4 (2)
C11—C10—C14—C1760.4 (3)C32—C33—C39—C4057.1 (3)
C13—C12—C18—C211.0 (3)C43—C44—C45—C46176.2 (2)
C11—C12—C18—C21175.1 (2)C47—N3—C46—C45176.0 (2)
C13—C12—C18—C20118.9 (2)C44—C45—C46—N3174.5 (2)
C11—C12—C18—C2057.3 (3)C46—N3—C47—C48178.62 (19)
C13—C12—C18—C19117.8 (3)N3—C47—C48—C49178.7 (2)
C11—C12—C18—C1966.0 (3)C47—C48—C49—C50177.0 (2)
O4—C22—C23—C247.1 (4)C51—C52—C53—C54175.1 (2)
O5—C22—C23—C24173.2 (2)C55—N4—C54—C53177.43 (19)
O4—C22—C23—C27174.4 (2)C52—C53—C54—N4177.9 (2)
O5—C22—C23—C275.3 (4)C54—N4—C55—C56173.89 (19)
C27—C23—C24—C251.0 (3)N4—C55—C56—C57175.4 (2)
C22—C23—C24—C25179.6 (2)C55—C56—C57—C58173.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H32···O20.881.952.826 (2)172
N3—H31···O50.881.992.820 (3)157
N4—H42···O20.881.972.816 (3)160
N4—H41···O50.881.962.834 (2)172
O3—H3o···O1i0.842.042.708 (3)135
O6—H6o···O4ii0.841.812.651 (3)175
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC8H20N+·C21H26NO3S
Mr502.74
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)23.4451 (3), 18.7712 (3), 12.9657 (2)
V3)5706.11 (15)
Z8
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.25 × 0.15 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.965, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
53030, 13074, 10355
Rint0.066
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.110, 1.07
No. of reflections13074
No. of parameters647
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.32
Absolute structureFlack (1983), 6221 Friedel pairs
Absolute structure parameter0.03 (6)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H32···O20.881.952.826 (2)172
N3—H31···O50.881.992.820 (3)157
N4—H42···O20.881.972.816 (3)160
N4—H41···O50.881.962.834 (2)172
O3—H3o···O1i0.842.042.708 (3)135
O6—H6o···O4ii0.841.812.651 (3)175
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.
 

Acknowledgements

We thank the University of Malaya (grant No. FS338/2008 A) for supporing this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKim, T. H. & Lee, N. (2003). Bull. Kor. Chem. Soc., 24, 1809–1813.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationUm, S.-I., Kang, Y.-H. & Lee, J.-Y. (2005). Dyes Pigm. 64, 93–99.  Web of Science CrossRef CAS Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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