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In the structure of the title lithium salt of pyridine-3-sulfonic acid, Li+·C5H4NO3S, apart from the electrostatic interactions between the lithium cations and the pyridine-3-sulfonate anions, the three-dimensional structure contains π–π interactions between pairs of pyridine moieties. The asymmetric unit contains two cations and two anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006191/lh6181sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006191/lh6181Isup2.hkl
Contains datablock I

CCDC reference: 238657

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.046
  • wR factor = 0.068
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O6 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O14 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O15 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... S3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... S13 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Li2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Xcalibur (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: CRYSTALS (Watkin et al., 2001).

(I) top
Crystal data top
Li+·C5H4NO3SZ = 4
Mr = 165.10F(000) = 336.000
Triclinic, P1Dx = 1.666 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6362 (6) ÅCell parameters from 4215 reflections
b = 8.8697 (9) Åθ = 2–29°
c = 10.397 (1) ŵ = 0.43 mm1
α = 81.572 (8)°T = 293 K
β = 71.486 (8)°Prism, colourless
γ = 82.921 (7)°0.52 × 0.33 × 0.22 mm
V = 658.33 (11) Å3
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
2612 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.07
Detector resolution: 17 pixels mm-1θmax = 32.2°, θmin = 3.3°
area detector scansh = 1011
11562 measured reflectionsk = 1212
4187 independent reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.068 %TMethod, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982). ηfilβreak [weight] = $1.0/[A_0T_0(x) + A_1T_1(x) ··· + A_{n-1}]T_{n-1}(x)]$
where A$_i$ are the Chebychev coefficients listed below and $x$ = F$_{µathrm{ }}$/F$_{µathrm{max}}.$ηfilβreak Method = Robust Weighting (Prince, 1982).ηfilβreak W = [weight] * [1-(Δelta F/6σigma F)$2$]$2$.ηfilβreak A$_{0-2}$ are 471.0, 539.0, and 166.0, respectively.
S = 1.22(Δ/σ)max = 0.001
4182 reflectionsΔρmax = 0.71 e Å3
199 parametersΔρmin = 0.68 e Å3
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Li10.4525 (5)0.1728 (4)0.8897 (4)0.0256
Li20.6333 (5)0.3261 (5)0.6222 (4)0.0284
S30.39921 (7)0.30511 (7)0.41227 (6)0.0239
O40.3310 (2)0.46386 (19)0.3996 (2)0.0468
O50.4545 (3)0.2402 (3)0.28501 (19)0.0560
O60.5412 (2)0.2755 (2)0.4794 (2)0.0422
C70.2063 (3)0.2079 (2)0.5192 (2)0.0210
C80.2296 (3)0.0658 (3)0.5888 (2)0.0303
C90.0729 (4)0.0046 (3)0.6670 (3)0.0356
C100.1000 (3)0.0696 (3)0.6764 (2)0.0334
N110.1234 (3)0.2072 (2)0.6098 (2)0.0296
C120.0287 (3)0.2739 (2)0.5324 (2)0.0252
S130.33457 (7)0.18748 (6)0.90474 (6)0.0217
O140.4717 (2)0.2681 (3)0.7986 (2)0.0538
O150.3245 (3)0.0326 (2)0.8825 (2)0.0485
O160.3489 (2)0.1966 (2)1.03882 (18)0.0418
C170.1181 (3)0.2859 (2)0.9025 (2)0.0204
C180.1087 (3)0.4251 (3)0.8247 (2)0.0286
C190.0667 (3)0.4959 (3)0.8303 (3)0.0332
C200.2201 (3)0.4241 (3)0.9101 (3)0.0320
N210.2129 (2)0.2894 (2)0.9866 (2)0.0285
C220.0436 (3)0.2226 (3)0.9812 (2)0.0243
H230.35330.01060.59290.0500*
H240.08120.10540.72460.0500*
H250.00950.36660.48120.0500*
H260.21440.47750.77540.0500*
H270.07460.60230.77070.0500*
H280.34980.46540.91130.0500*
H290.03300.11841.03500.0500*
H50.21100.01490.72570.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.0231 (18)0.026 (2)0.029 (2)0.0006 (15)0.0092 (16)0.0058 (16)
Li20.0199 (18)0.030 (2)0.033 (2)0.0040 (15)0.0059 (16)0.0023 (17)
S30.0200 (2)0.0263 (3)0.0260 (3)0.0021 (2)0.0065 (2)0.0057 (2)
O40.034 (1)0.0211 (9)0.0809 (15)0.0058 (7)0.016 (1)0.0085 (9)
O50.0524 (12)0.0842 (16)0.029 (1)0.0261 (11)0.0069 (9)0.0259 (11)
O60.0272 (9)0.0531 (12)0.0542 (12)0.0044 (8)0.0233 (8)0.005 (1)
C70.0208 (9)0.021 (1)0.020 (1)0.0010 (8)0.0040 (8)0.0060 (8)
C80.0303 (12)0.0268 (12)0.0317 (13)0.0079 (9)0.010 (1)0.004 (1)
C90.0423 (14)0.0253 (12)0.0344 (14)0.001 (1)0.0096 (11)0.005 (1)
C100.0304 (12)0.0335 (13)0.0322 (13)0.008 (1)0.004 (1)0.001 (1)
N110.0214 (9)0.031 (1)0.0349 (11)0.0030 (8)0.0057 (8)0.0043 (8)
C120.022 (1)0.020 (1)0.0314 (12)0.0008 (8)0.0077 (9)0.0011 (9)
S130.0147 (2)0.0252 (3)0.0238 (3)0.00152 (19)0.00452 (19)0.0013 (2)
O140.0224 (9)0.0687 (14)0.0499 (12)0.0059 (9)0.0056 (8)0.0216 (11)
O150.039 (1)0.0261 (9)0.0931 (17)0.0103 (8)0.0377 (11)0.020 (1)
O160.0316 (9)0.0625 (13)0.037 (1)0.0142 (9)0.0199 (8)0.0164 (9)
C170.0186 (9)0.024 (1)0.020 (1)0.0002 (7)0.0076 (8)0.0032 (8)
C180.0253 (11)0.0279 (12)0.0295 (12)0.0033 (9)0.0063 (9)0.0030 (9)
C190.0356 (13)0.0278 (12)0.0359 (14)0.005 (1)0.0152 (11)0.001 (1)
C200.0266 (11)0.0340 (13)0.0379 (14)0.008 (1)0.015 (1)0.0086 (11)
N210.0163 (8)0.0331 (11)0.0354 (11)0.0016 (7)0.0064 (8)0.0085 (9)
C220.0181 (9)0.0253 (11)0.0277 (11)0.0002 (8)0.0057 (8)0.0020 (9)
Geometric parameters (Å, º) top
S3—O41.4421 (18)N21—C221.342 (3)
S3—O51.438 (2)N21—Li1v2.157 (4)
S3—O61.4451 (18)C7—C81.380 (3)
S3—C71.772 (2)C7—C121.382 (3)
S13—O141.430 (2)C8—C91.379 (4)
S13—O151.4412 (19)C9—C101.382 (4)
S13—O161.4471 (18)C17—C181.381 (3)
S13—C171.777 (2)C17—C221.380 (3)
O4—Li2i1.886 (5)C18—C191.395 (4)
O5—Li1ii1.886 (4)C19—C201.370 (4)
O6—Li21.959 (4)C8—H231.0194
O14—Li21.896 (4)C9—H241.0076
O15—Li11.962 (4)C10—H50.9844
O16—Li1iii1.868 (4)C12—H250.9341
N11—C101.333 (3)C18—H260.9435
N11—C121.335 (3)C19—H271.0567
N11—Li2iv1.996 (5)C20—H281.0096
N21—C201.340 (3)C22—H291.0161
S3···H23ii3.1767C18···Li23.946 (5)
O4···N11vi3.148 (3)C19···C17x3.509 (3)
O4···O6i3.173 (2)C20···Li2iv3.755 (5)
O4···O14i3.105 (3)C9···H29v3.0448
O4···C12vi3.336 (3)C22···H24v3.0171
O5···O15ii3.178 (3)C22···H29v3.0281
O5···O16vii3.005 (3)Li2···C20viii3.755 (5)
O6···O4i3.173 (2)Li2···C183.946 (5)
O6···N11viii3.217 (3)Li1···H28xi3.3819
O6···O143.182 (3)Li1···H5viii3.1179
O6···C8ii3.356 (3)Li2···H263.3023
O14···O4i3.105 (3)H5···Li1iv3.1179
O14···O63.182 (3)H5···O16v2.8505
O14···N11viii3.122 (3)H23···O62.8133
O15···N21v3.076 (3)H23···S3ii3.1767
O15···C22v3.172 (3)H23···O5ii2.8748
O15···O5ii3.178 (3)H23···O6ii2.7063
O15···C83.321 (3)H23···H23ii2.4578
O16···O5ix3.005 (3)H24···C22v3.0171
O4···H25vi2.8450H24···H29v2.3953
O4···H252.5448H25···O42.5448
O5···H23ii2.8748H25···O4vi2.8450
O6···H23ii2.7063H25···H25vi2.4340
O6···H232.8133H25···H27vi2.4855
O14···H28viii2.9149H26···O142.5765
O14···H262.5765H26···Li23.3023
O15···H292.7638H27···H25vi2.4855
O15···H29v2.5826H28···O14iv2.9149
O16···H5v2.8505H28···Li1xii3.3819
N11···O6iv3.217 (3)H28···H28xiii2.5176
N11···O14iv3.122 (3)H29···O152.7638
N11···O4vi3.148 (3)H29···O15v2.5826
N21···O15v3.076 (3)H29···C9v3.0448
C8···O153.321 (3)H29···C22v3.0281
C8···O6ii3.356 (3)H29···H24v2.3953
C12···O4vi3.336 (3)H29···H29v2.2692
C17···C19x3.509 (3)
O4—S3—O5112.89 (13)C18—C17—C22119.4 (2)
O4—S3—O6113.56 (11)C17—C18—C19117.7 (2)
O4—S3—C7105.19 (10)C18—C19—C20119.1 (2)
O5—S3—O6111.89 (13)N21—C20—C19123.9 (2)
O5—S3—C7105.83 (12)N21—C22—C17123.3 (2)
O6—S3—C7106.72 (11)C9—C8—H23116.41
O14—S13—O15114.17 (14)C7—C8—H23125.58
O14—S13—O16112.37 (11)C8—C9—H24121.41
O14—S13—C17105.67 (11)C10—C9—H24118.64
O15—S13—O16112.16 (11)N11—C10—H5117.90
O15—S13—C17105.82 (12)C9—C10—H5119.10
O16—S13—C17105.84 (10)N11—C12—H25116.14
S3—O4—Li2i151.12 (17)C7—C12—H25120.38
S3—O5—Li1ii173.2 (2)C17—C18—H26122.81
S3—O6—Li2147.00 (17)C19—C18—H26119.28
S13—O14—Li2159.6 (2)C20—C19—H27123.01
S13—O15—Li1142.25 (19)C18—C19—H27117.93
S13—O16—Li1iii133.49 (16)N21—C20—H28113.67
C10—N11—C12117.4 (2)C19—C20—H28122.33
C10—N11—Li2iv125.5 (2)N21—C22—H29118.71
C12—N11—Li2iv117.07 (19)C17—C22—H29117.92
C20—N21—C22116.6 (2)O15—Li1—N21v96.50 (18)
C20—N21—Li1v124.44 (18)O5ii—Li1—O15111.4 (2)
C22—N21—Li1v118.89 (18)O5ii—Li1—N21v111.1 (2)
S3—C7—C8121.20 (18)O16iii—Li1—N21v115.1 (2)
S3—C7—C12119.83 (14)O15—Li1—O16iii116.3 (2)
C8—C7—C12119.0 (2)O5ii—Li1—O16iii106.4 (2)
C7—C8—C9117.9 (2)O6—Li2—N11viii108.8 (2)
C8—C9—C10119.7 (2)O4i—Li2—O6111.2 (2)
N11—C10—C9122.7 (2)O6—Li2—O14111.3 (2)
N11—C12—C7123.34 (18)O4i—Li2—O14110.4 (2)
S13—C17—C18121.27 (18)O4i—Li2—N11viii108.3 (2)
S13—C17—C22119.29 (16)O14—Li2—N11viii106.7 (2)
O5—S3—O4—Li2i96.8 (4)S13—O14—Li2—N11viii93.4 (6)
O6—S3—O4—Li2i31.9 (4)S13—O14—Li2—O625.1 (7)
C7—S3—O4—Li2i148.3 (4)S13—O15—Li1—O16iii6.6 (4)
O4—S3—O6—Li236.5 (3)S13—O15—Li1—N21v128.8 (2)
O5—S3—O6—Li2165.8 (3)S13—O15—Li1—O5ii115.5 (3)
C7—S3—O6—Li278.9 (3)S13iii—O16iii—Li1—O1566.0 (3)
O4—S3—C7—C8159.12 (18)C12viii—N11viii—Li2—O691.6 (2)
O4—S3—C7—C1221.7 (2)C10viii—N11viii—Li2—O1429.0 (3)
O5—S3—C7—C881.2 (2)C10viii—N11viii—Li2—O691.1 (3)
O5—S3—C7—C1298.03 (19)Li2iv—N11—C12—C7177.1 (2)
O6—S3—C7—C838.2 (2)C12—N11—C10—C90.5 (3)
O6—S3—C7—C12142.64 (17)C12viii—N11viii—Li2—O14148.2 (2)
O15—S13—O14—Li228.4 (6)C10—N11—C12—C70.4 (3)
O16—S13—O14—Li2157.6 (5)Li2iv—N11—C10—C9177.7 (2)
C17—S13—O14—Li287.5 (6)Li1v—N21—C20—C19179.0 (2)
O14—S13—O15—Li175.9 (3)C20—N21—C22—C170.2 (3)
O16—S13—O15—Li153.4 (3)Li1v—N21—C22—C17178.3 (2)
C17—S13—O15—Li1168.3 (3)C22—N21—C20—C191.0 (4)
O14—S13—O16—Li1iii45.7 (3)C22v—N21v—Li1—O1520.6 (3)
O15—S13—O16—Li1iii84.5 (2)C20v—N21v—Li1—O15157.4 (2)
C17—S13—O16—Li1iii160.6 (2)C8—C7—C12—N110.1 (3)
O14—S13—C17—C189.7 (2)S3—C7—C12—N11179.31 (16)
O14—S13—C17—C22171.02 (18)C12—C7—C8—C91.0 (3)
O15—S13—C17—C18131.09 (18)S3—C7—C8—C9178.21 (19)
O15—S13—C17—C2249.6 (2)C7—C8—C9—C101.8 (4)
O16—S13—C17—C18109.70 (18)C8—C9—C10—N111.6 (4)
O16—S13—C17—C2269.61 (19)S13—C17—C18—C19179.04 (18)
S3i—O4i—Li2—O1467.9 (4)S13—C17—C22—N21179.45 (17)
S3i—O4i—Li2—O656.2 (5)C22—C17—C18—C190.3 (3)
S3—O6—Li2—O1466.7 (4)C18—C17—C22—N210.1 (3)
S3—O6—Li2—N11viii176.1 (2)C17—C18—C19—C201.0 (4)
S3—O6—Li2—O4i56.9 (4)C18—C19—C20—N211.4 (4)
S13—O14—Li2—O4i149.1 (5)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1; (iii) x+1, y, z+2; (iv) x1, y, z; (v) x, y, z+2; (vi) x, y+1, z+1; (vii) x, y, z1; (viii) x+1, y, z; (ix) x, y, z+1; (x) x, y+1, z+2; (xi) x+1, y1, z; (xii) x1, y+1, z; (xiii) x1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H25···O40.932.542.886 (3)102
C18—H26···O140.942.582.895 (3)100
C22—H29···O15v1.022.583.172 (3)117
Symmetry code: (v) x, y, z+2.
 

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