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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1799.
Published online 2008 August 20. doi:  10.1107/S1600536808026202
PMCID: PMC2960651

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

Abstract

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 [triangle]); Um et al. (2005 [triangle]).

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Object name is e-64-o1799-scheme1.jpg

Experimental

Crystal data

  • C8H20N+·C21H26NO3S
  • M r = 502.74
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1799-efi1.jpg
  • 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 [triangle]) T min = 0.965, T max = 0.993
  • 53030 measured reflections
  • 13074 independent reflections
  • 10355 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 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 [triangle]), 6221 Friedel pairs
  • Flack parameter: 0.03 (6)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026202/lh2682sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026202/lh2682Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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 ...

Crystal data

C8H20N+·C21H26NO3SF000 = 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 = 2.2–25.1º
b = 18.7712 (3) ŵ = 0.15 mm1
c = 12.9657 (2) ÅT = 293 (2) K
V = 5706.11 (15) Å3Prism, colorless
Z = 80.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer13074 independent reflections
Radiation source: fine-focus sealed tube10355 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.1º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −30→30
Tmin = 0.965, Tmax = 0.993k = −24→24
53030 measured reflectionsl = −16→16

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046  w = 1/[σ2(Fo2) + (0.047P)2 + 0.106P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max = 0.002
S = 1.07Δρmax = 0.37 e Å3
13074 reflectionsΔρmin = −0.32 e Å3
647 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 6221 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (6)
Secondary atom site location: difference Fourier map

Special details

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)

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)
H3O0.60430.1669−0.04180.041*
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)
H50.7402−0.03090.67420.031*
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)
H16A0.75710.2091−0.02890.040*
H16B0.69340.1822−0.04990.040*
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)
H19A0.53300.0793−0.04380.040*
H19B0.47490.0383−0.01730.040*
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)
H21A0.4913−0.00470.18830.046*
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)

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, °)

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—C3−2.0 (3)C23—C24—C25—C260.1 (4)
O2—C1—C2—C3177.9 (2)C27—N2—C26—C25−0.1 (4)
O1—C1—C2—C6177.0 (2)C24—C25—C26—N20.5 (4)
O2—C1—C2—C6−3.1 (4)C26—N2—C27—C23−1.0 (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—C5−1.3 (4)C22—C23—C27—N2−180.0 (2)
C6—N1—C5—C40.4 (4)C24—C23—C27—S2−179.28 (17)
C3—C4—C5—N11.1 (4)C22—C23—C27—S2−0.8 (3)
C5—N1—C6—C2−1.7 (4)C28—S2—C27—N2−1.2 (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—N1−177.5 (2)S2—C28—C29—C30−100.7 (2)
C3—C2—C6—S1−177.98 (18)S2—C28—C29—C3477.8 (2)
C1—C2—C6—S13.0 (3)C34—C29—C30—C31−0.3 (4)
C7—S1—C6—N12.7 (2)C28—C29—C30—C31178.2 (2)
C7—S1—C6—C2−177.7 (2)C29—C30—C31—C32−1.1 (3)
C6—S1—C7—C8−170.89 (18)C29—C30—C31—C35176.7 (2)
S1—C7—C8—C13−77.3 (3)C30—C31—C32—O6−173.2 (2)
S1—C7—C8—C9101.1 (2)C35—C31—C32—O69.1 (3)
C13—C8—C9—C10−0.9 (4)C30—C31—C32—C331.5 (3)
C7—C8—C9—C10−179.4 (2)C35—C31—C32—C33−176.2 (2)
C8—C9—C10—C111.4 (4)O6—C32—C33—C34174.2 (2)
C8—C9—C10—C14−176.9 (2)C31—C32—C33—C34−0.5 (3)
C9—C10—C11—O3177.0 (2)O6—C32—C33—C39−5.3 (3)
C14—C10—C11—O3−4.6 (3)C31—C32—C33—C39180.0 (2)
C9—C10—C11—C12−0.3 (4)C30—C29—C34—C331.4 (4)
C14—C10—C11—C12178.0 (2)C28—C29—C34—C33−177.1 (2)
O3—C11—C12—C13−178.4 (2)C32—C33—C34—C29−1.0 (3)
C10—C11—C12—C13−1.2 (3)C39—C33—C34—C29178.5 (2)
O3—C11—C12—C18−2.1 (4)C30—C31—C35—C362.6 (3)
C10—C11—C12—C18175.1 (2)C32—C31—C35—C36−179.8 (2)
C9—C8—C13—C12−0.7 (4)C30—C31—C35—C38123.5 (2)
C7—C8—C13—C12177.7 (2)C32—C31—C35—C38−58.9 (3)
C11—C12—C13—C81.7 (3)C30—C31—C35—C37−115.6 (2)
C18—C12—C13—C8−174.7 (2)C32—C31—C35—C3762.1 (3)
C9—C10—C14—C15−1.9 (3)C34—C33—C39—C424.3 (3)
C11—C10—C14—C15179.8 (2)C32—C33—C39—C42−176.2 (2)
C9—C10—C14—C16116.5 (3)C34—C33—C39—C41−114.5 (2)
C11—C10—C14—C16−61.8 (3)C32—C33—C39—C4165.0 (3)
C9—C10—C14—C17−121.4 (3)C34—C33—C39—C40123.4 (2)
C11—C10—C14—C1760.4 (3)C32—C33—C39—C40−57.1 (3)
C13—C12—C18—C211.0 (3)C43—C44—C45—C46−176.2 (2)
C11—C12—C18—C21−175.1 (2)C47—N3—C46—C45176.0 (2)
C13—C12—C18—C20118.9 (2)C44—C45—C46—N3−174.5 (2)
C11—C12—C18—C20−57.3 (3)C46—N3—C47—C48178.62 (19)
C13—C12—C18—C19−117.8 (3)N3—C47—C48—C49−178.7 (2)
C11—C12—C18—C1966.0 (3)C47—C48—C49—C50177.0 (2)
O4—C22—C23—C24−7.1 (4)C51—C52—C53—C54175.1 (2)
O5—C22—C23—C24173.2 (2)C55—N4—C54—C53−177.43 (19)
O4—C22—C23—C27174.4 (2)C52—C53—C54—N4177.9 (2)
O5—C22—C23—C27−5.3 (4)C54—N4—C55—C56−173.89 (19)
C27—C23—C24—C25−1.0 (3)N4—C55—C56—C57175.4 (2)
C22—C23—C24—C25−179.6 (2)C55—C56—C57—C58−173.4 (2)

Hydrogen-bond geometry (Å, °)

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, z−1; (ii) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2682).

References

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