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
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
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).
Crystal data top
Li+·C5H4NO3S− | Z = 4 |
Mr = 165.10 | F(000) = 336.000 |
Triclinic, P1 | Dx = 1.666 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6362 (6) Å | Cell parameters from 4215 reflections |
b = 8.8697 (9) Å | θ = 2–29° |
c = 10.397 (1) Å | µ = 0.43 mm−1 |
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 monochromator | Rint = 0.07 |
Detector resolution: 17 pixels mm-1 | θmax = 32.2°, θmin = 3.3° |
area detector scans | h = −10→11 |
11562 measured reflections | k = −12→12 |
4187 independent reflections | l = −14→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-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 reflections | Δρmax = 0.71 e Å−3 |
199 parameters | Δρmin = −0.68 e Å−3 |
0 restraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Li1 | 0.4525 (5) | −0.1728 (4) | 0.8897 (4) | 0.0256 | |
Li2 | 0.6333 (5) | 0.3261 (5) | 0.6222 (4) | 0.0284 | |
S3 | 0.39921 (7) | 0.30511 (7) | 0.41227 (6) | 0.0239 | |
O4 | 0.3310 (2) | 0.46386 (19) | 0.3996 (2) | 0.0468 | |
O5 | 0.4545 (3) | 0.2402 (3) | 0.28501 (19) | 0.0560 | |
O6 | 0.5412 (2) | 0.2755 (2) | 0.4794 (2) | 0.0422 | |
C7 | 0.2063 (3) | 0.2079 (2) | 0.5192 (2) | 0.0210 | |
C8 | 0.2296 (3) | 0.0658 (3) | 0.5888 (2) | 0.0303 | |
C9 | 0.0729 (4) | −0.0046 (3) | 0.6670 (3) | 0.0356 | |
C10 | −0.1000 (3) | 0.0696 (3) | 0.6764 (2) | 0.0334 | |
N11 | −0.1234 (3) | 0.2072 (2) | 0.6098 (2) | 0.0296 | |
C12 | 0.0287 (3) | 0.2739 (2) | 0.5324 (2) | 0.0252 | |
S13 | 0.33457 (7) | 0.18748 (6) | 0.90474 (6) | 0.0217 | |
O14 | 0.4717 (2) | 0.2681 (3) | 0.7986 (2) | 0.0538 | |
O15 | 0.3245 (3) | 0.0326 (2) | 0.8825 (2) | 0.0485 | |
O16 | 0.3489 (2) | 0.1966 (2) | 1.03882 (18) | 0.0418 | |
C17 | 0.1181 (3) | 0.2859 (2) | 0.9025 (2) | 0.0204 | |
C18 | 0.1087 (3) | 0.4251 (3) | 0.8247 (2) | 0.0286 | |
C19 | −0.0667 (3) | 0.4959 (3) | 0.8303 (3) | 0.0332 | |
C20 | −0.2201 (3) | 0.4241 (3) | 0.9101 (3) | 0.0320 | |
N21 | −0.2129 (2) | 0.2894 (2) | 0.9866 (2) | 0.0285 | |
C22 | −0.0436 (3) | 0.2226 (3) | 0.9812 (2) | 0.0243 | |
H23 | 0.3533 | 0.0106 | 0.5929 | 0.0500* | |
H24 | 0.0812 | −0.1054 | 0.7246 | 0.0500* | |
H25 | 0.0095 | 0.3666 | 0.4812 | 0.0500* | |
H26 | 0.2144 | 0.4775 | 0.7754 | 0.0500* | |
H27 | −0.0746 | 0.6023 | 0.7707 | 0.0500* | |
H28 | −0.3498 | 0.4654 | 0.9113 | 0.0500* | |
H29 | −0.0330 | 0.1184 | 1.0350 | 0.0500* | |
H5 | −0.2110 | 0.0149 | 0.7257 | 0.0500* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Li1 | 0.0231 (18) | 0.026 (2) | 0.029 (2) | −0.0006 (15) | −0.0092 (16) | −0.0058 (16) |
Li2 | 0.0199 (18) | 0.030 (2) | 0.033 (2) | −0.0040 (15) | −0.0059 (16) | 0.0023 (17) |
S3 | 0.0200 (2) | 0.0263 (3) | 0.0260 (3) | −0.0021 (2) | −0.0065 (2) | −0.0057 (2) |
O4 | 0.034 (1) | 0.0211 (9) | 0.0809 (15) | −0.0058 (7) | −0.016 (1) | 0.0085 (9) |
O5 | 0.0524 (12) | 0.0842 (16) | 0.029 (1) | −0.0261 (11) | 0.0069 (9) | −0.0259 (11) |
O6 | 0.0272 (9) | 0.0531 (12) | 0.0542 (12) | −0.0044 (8) | −0.0233 (8) | −0.005 (1) |
C7 | 0.0208 (9) | 0.021 (1) | 0.020 (1) | 0.0010 (8) | −0.0040 (8) | −0.0060 (8) |
C8 | 0.0303 (12) | 0.0268 (12) | 0.0317 (13) | 0.0079 (9) | −0.010 (1) | −0.004 (1) |
C9 | 0.0423 (14) | 0.0253 (12) | 0.0344 (14) | −0.001 (1) | −0.0096 (11) | 0.005 (1) |
C10 | 0.0304 (12) | 0.0335 (13) | 0.0322 (13) | −0.008 (1) | −0.004 (1) | 0.001 (1) |
N11 | 0.0214 (9) | 0.031 (1) | 0.0349 (11) | −0.0030 (8) | −0.0057 (8) | −0.0043 (8) |
C12 | 0.022 (1) | 0.020 (1) | 0.0314 (12) | 0.0008 (8) | −0.0077 (9) | −0.0011 (9) |
S13 | 0.0147 (2) | 0.0252 (3) | 0.0238 (3) | −0.00152 (19) | −0.00452 (19) | −0.0013 (2) |
O14 | 0.0224 (9) | 0.0687 (14) | 0.0499 (12) | −0.0059 (9) | 0.0056 (8) | 0.0216 (11) |
O15 | 0.039 (1) | 0.0261 (9) | 0.0931 (17) | 0.0103 (8) | −0.0377 (11) | −0.020 (1) |
O16 | 0.0316 (9) | 0.0625 (13) | 0.037 (1) | 0.0142 (9) | −0.0199 (8) | −0.0164 (9) |
C17 | 0.0186 (9) | 0.024 (1) | 0.020 (1) | −0.0002 (7) | −0.0076 (8) | −0.0032 (8) |
C18 | 0.0253 (11) | 0.0279 (12) | 0.0295 (12) | −0.0033 (9) | −0.0063 (9) | 0.0030 (9) |
C19 | 0.0356 (13) | 0.0278 (12) | 0.0359 (14) | 0.005 (1) | −0.0152 (11) | 0.001 (1) |
C20 | 0.0266 (11) | 0.0340 (13) | 0.0379 (14) | 0.008 (1) | −0.015 (1) | −0.0086 (11) |
N21 | 0.0163 (8) | 0.0331 (11) | 0.0354 (11) | 0.0016 (7) | −0.0064 (8) | −0.0085 (9) |
C22 | 0.0181 (9) | 0.0253 (11) | 0.0277 (11) | 0.0002 (8) | −0.0057 (8) | −0.0020 (9) |
Geometric parameters (Å, º) top
S3—O4 | 1.4421 (18) | N21—C22 | 1.342 (3) |
S3—O5 | 1.438 (2) | N21—Li1v | 2.157 (4) |
S3—O6 | 1.4451 (18) | C7—C8 | 1.380 (3) |
S3—C7 | 1.772 (2) | C7—C12 | 1.382 (3) |
S13—O14 | 1.430 (2) | C8—C9 | 1.379 (4) |
S13—O15 | 1.4412 (19) | C9—C10 | 1.382 (4) |
S13—O16 | 1.4471 (18) | C17—C18 | 1.381 (3) |
S13—C17 | 1.777 (2) | C17—C22 | 1.380 (3) |
O4—Li2i | 1.886 (5) | C18—C19 | 1.395 (4) |
O5—Li1ii | 1.886 (4) | C19—C20 | 1.370 (4) |
O6—Li2 | 1.959 (4) | C8—H23 | 1.0194 |
O14—Li2 | 1.896 (4) | C9—H24 | 1.0076 |
O15—Li1 | 1.962 (4) | C10—H5 | 0.9844 |
O16—Li1iii | 1.868 (4) | C12—H25 | 0.9341 |
N11—C10 | 1.333 (3) | C18—H26 | 0.9435 |
N11—C12 | 1.335 (3) | C19—H27 | 1.0567 |
N11—Li2iv | 1.996 (5) | C20—H28 | 1.0096 |
N21—C20 | 1.340 (3) | C22—H29 | 1.0161 |
| | | |
S3···H23ii | 3.1767 | C18···Li2 | 3.946 (5) |
O4···N11vi | 3.148 (3) | C19···C17x | 3.509 (3) |
O4···O6i | 3.173 (2) | C20···Li2iv | 3.755 (5) |
O4···O14i | 3.105 (3) | C9···H29v | 3.0448 |
O4···C12vi | 3.336 (3) | C22···H24v | 3.0171 |
O5···O15ii | 3.178 (3) | C22···H29v | 3.0281 |
O5···O16vii | 3.005 (3) | Li2···C20viii | 3.755 (5) |
O6···O4i | 3.173 (2) | Li2···C18 | 3.946 (5) |
O6···N11viii | 3.217 (3) | Li1···H28xi | 3.3819 |
O6···O14 | 3.182 (3) | Li1···H5viii | 3.1179 |
O6···C8ii | 3.356 (3) | Li2···H26 | 3.3023 |
O14···O4i | 3.105 (3) | H5···Li1iv | 3.1179 |
O14···O6 | 3.182 (3) | H5···O16v | 2.8505 |
O14···N11viii | 3.122 (3) | H23···O6 | 2.8133 |
O15···N21v | 3.076 (3) | H23···S3ii | 3.1767 |
O15···C22v | 3.172 (3) | H23···O5ii | 2.8748 |
O15···O5ii | 3.178 (3) | H23···O6ii | 2.7063 |
O15···C8 | 3.321 (3) | H23···H23ii | 2.4578 |
O16···O5ix | 3.005 (3) | H24···C22v | 3.0171 |
O4···H25vi | 2.8450 | H24···H29v | 2.3953 |
O4···H25 | 2.5448 | H25···O4 | 2.5448 |
O5···H23ii | 2.8748 | H25···O4vi | 2.8450 |
O6···H23ii | 2.7063 | H25···H25vi | 2.4340 |
O6···H23 | 2.8133 | H25···H27vi | 2.4855 |
O14···H28viii | 2.9149 | H26···O14 | 2.5765 |
O14···H26 | 2.5765 | H26···Li2 | 3.3023 |
O15···H29 | 2.7638 | H27···H25vi | 2.4855 |
O15···H29v | 2.5826 | H28···O14iv | 2.9149 |
O16···H5v | 2.8505 | H28···Li1xii | 3.3819 |
N11···O6iv | 3.217 (3) | H28···H28xiii | 2.5176 |
N11···O14iv | 3.122 (3) | H29···O15 | 2.7638 |
N11···O4vi | 3.148 (3) | H29···O15v | 2.5826 |
N21···O15v | 3.076 (3) | H29···C9v | 3.0448 |
C8···O15 | 3.321 (3) | H29···C22v | 3.0281 |
C8···O6ii | 3.356 (3) | H29···H24v | 2.3953 |
C12···O4vi | 3.336 (3) | H29···H29v | 2.2692 |
C17···C19x | 3.509 (3) | | |
| | | |
O4—S3—O5 | 112.89 (13) | C18—C17—C22 | 119.4 (2) |
O4—S3—O6 | 113.56 (11) | C17—C18—C19 | 117.7 (2) |
O4—S3—C7 | 105.19 (10) | C18—C19—C20 | 119.1 (2) |
O5—S3—O6 | 111.89 (13) | N21—C20—C19 | 123.9 (2) |
O5—S3—C7 | 105.83 (12) | N21—C22—C17 | 123.3 (2) |
O6—S3—C7 | 106.72 (11) | C9—C8—H23 | 116.41 |
O14—S13—O15 | 114.17 (14) | C7—C8—H23 | 125.58 |
O14—S13—O16 | 112.37 (11) | C8—C9—H24 | 121.41 |
O14—S13—C17 | 105.67 (11) | C10—C9—H24 | 118.64 |
O15—S13—O16 | 112.16 (11) | N11—C10—H5 | 117.90 |
O15—S13—C17 | 105.82 (12) | C9—C10—H5 | 119.10 |
O16—S13—C17 | 105.84 (10) | N11—C12—H25 | 116.14 |
S3—O4—Li2i | 151.12 (17) | C7—C12—H25 | 120.38 |
S3—O5—Li1ii | 173.2 (2) | C17—C18—H26 | 122.81 |
S3—O6—Li2 | 147.00 (17) | C19—C18—H26 | 119.28 |
S13—O14—Li2 | 159.6 (2) | C20—C19—H27 | 123.01 |
S13—O15—Li1 | 142.25 (19) | C18—C19—H27 | 117.93 |
S13—O16—Li1iii | 133.49 (16) | N21—C20—H28 | 113.67 |
C10—N11—C12 | 117.4 (2) | C19—C20—H28 | 122.33 |
C10—N11—Li2iv | 125.5 (2) | N21—C22—H29 | 118.71 |
C12—N11—Li2iv | 117.07 (19) | C17—C22—H29 | 117.92 |
C20—N21—C22 | 116.6 (2) | O15—Li1—N21v | 96.50 (18) |
C20—N21—Li1v | 124.44 (18) | O5ii—Li1—O15 | 111.4 (2) |
C22—N21—Li1v | 118.89 (18) | O5ii—Li1—N21v | 111.1 (2) |
S3—C7—C8 | 121.20 (18) | O16iii—Li1—N21v | 115.1 (2) |
S3—C7—C12 | 119.83 (14) | O15—Li1—O16iii | 116.3 (2) |
C8—C7—C12 | 119.0 (2) | O5ii—Li1—O16iii | 106.4 (2) |
C7—C8—C9 | 117.9 (2) | O6—Li2—N11viii | 108.8 (2) |
C8—C9—C10 | 119.7 (2) | O4i—Li2—O6 | 111.2 (2) |
N11—C10—C9 | 122.7 (2) | O6—Li2—O14 | 111.3 (2) |
N11—C12—C7 | 123.34 (18) | O4i—Li2—O14 | 110.4 (2) |
S13—C17—C18 | 121.27 (18) | O4i—Li2—N11viii | 108.3 (2) |
S13—C17—C22 | 119.29 (16) | O14—Li2—N11viii | 106.7 (2) |
| | | |
O5—S3—O4—Li2i | −96.8 (4) | S13—O14—Li2—N11viii | −93.4 (6) |
O6—S3—O4—Li2i | 31.9 (4) | S13—O14—Li2—O6 | 25.1 (7) |
C7—S3—O4—Li2i | 148.3 (4) | S13—O15—Li1—O16iii | 6.6 (4) |
O4—S3—O6—Li2 | 36.5 (3) | S13—O15—Li1—N21v | 128.8 (2) |
O5—S3—O6—Li2 | 165.8 (3) | S13—O15—Li1—O5ii | −115.5 (3) |
C7—S3—O6—Li2 | −78.9 (3) | S13iii—O16iii—Li1—O15 | 66.0 (3) |
O4—S3—C7—C8 | −159.12 (18) | C12viii—N11viii—Li2—O6 | 91.6 (2) |
O4—S3—C7—C12 | 21.7 (2) | C10viii—N11viii—Li2—O14 | 29.0 (3) |
O5—S3—C7—C8 | 81.2 (2) | C10viii—N11viii—Li2—O6 | −91.1 (3) |
O5—S3—C7—C12 | −98.03 (19) | Li2iv—N11—C12—C7 | 177.1 (2) |
O6—S3—C7—C8 | −38.2 (2) | C12—N11—C10—C9 | −0.5 (3) |
O6—S3—C7—C12 | 142.64 (17) | C12viii—N11viii—Li2—O14 | −148.2 (2) |
O15—S13—O14—Li2 | 28.4 (6) | C10—N11—C12—C7 | −0.4 (3) |
O16—S13—O14—Li2 | 157.6 (5) | Li2iv—N11—C10—C9 | −177.7 (2) |
C17—S13—O14—Li2 | −87.5 (6) | Li1v—N21—C20—C19 | −179.0 (2) |
O14—S13—O15—Li1 | 75.9 (3) | C20—N21—C22—C17 | 0.2 (3) |
O16—S13—O15—Li1 | −53.4 (3) | Li1v—N21—C22—C17 | 178.3 (2) |
C17—S13—O15—Li1 | −168.3 (3) | C22—N21—C20—C19 | −1.0 (4) |
O14—S13—O16—Li1iii | −45.7 (3) | C22v—N21v—Li1—O15 | 20.6 (3) |
O15—S13—O16—Li1iii | 84.5 (2) | C20v—N21v—Li1—O15 | −157.4 (2) |
C17—S13—O16—Li1iii | −160.6 (2) | C8—C7—C12—N11 | 0.1 (3) |
O14—S13—C17—C18 | −9.7 (2) | S3—C7—C12—N11 | 179.31 (16) |
O14—S13—C17—C22 | 171.02 (18) | C12—C7—C8—C9 | 1.0 (3) |
O15—S13—C17—C18 | −131.09 (18) | S3—C7—C8—C9 | −178.21 (19) |
O15—S13—C17—C22 | 49.6 (2) | C7—C8—C9—C10 | −1.8 (4) |
O16—S13—C17—C18 | 109.70 (18) | C8—C9—C10—N11 | 1.6 (4) |
O16—S13—C17—C22 | −69.61 (19) | S13—C17—C18—C19 | −179.04 (18) |
S3i—O4i—Li2—O14 | −67.9 (4) | S13—C17—C22—N21 | 179.45 (17) |
S3i—O4i—Li2—O6 | 56.2 (5) | C22—C17—C18—C19 | 0.3 (3) |
S3—O6—Li2—O14 | 66.7 (4) | C18—C17—C22—N21 | 0.1 (3) |
S3—O6—Li2—N11viii | −176.1 (2) | C17—C18—C19—C20 | −1.0 (4) |
S3—O6—Li2—O4i | −56.9 (4) | C18—C19—C20—N21 | 1.4 (4) |
S13—O14—Li2—O4i | 149.1 (5) | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z+2; (iv) x−1, y, z; (v) −x, −y, −z+2; (vi) −x, −y+1, −z+1; (vii) x, y, z−1; (viii) x+1, y, z; (ix) x, y, z+1; (x) −x, −y+1, −z+2; (xi) x+1, y−1, z; (xii) x−1, y+1, z; (xiii) −x−1, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H25···O4 | 0.93 | 2.54 | 2.886 (3) | 102 |
C18—H26···O14 | 0.94 | 2.58 | 2.895 (3) | 100 |
C22—H29···O15v | 1.02 | 2.58 | 3.172 (3) | 117 |
Symmetry code: (v) −x, −y, −z+2. |