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The asymmetric unit of the title compound, C7H10N+·C7H4NO3S, is composed of one saccharinate anion and one 2,6-dimethyl­pyridinium cation. They are linked by an N—H...O hydrogen bond. Furthermore, π–π inter­actions are observed between saccharinate anions and 2,6-dimethyl­pyridinium cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015297/hk2031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015297/hk2031Isup2.hkl
Contains datablock I

CCDC reference: 610805

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.049
  • wR factor = 0.140
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2,6-Dimethylpyridinium saccharinate top
Crystal data top
C7H10N+·C7H4NO3SF(000) = 608
Mr = 290.33Dx = 1.384 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2471 reflections
a = 12.5366 (18) Åθ = 2.8–27.5°
b = 8.2522 (11) ŵ = 0.24 mm1
c = 14.710 (2) ÅT = 292 K
β = 113.674 (2)°Block, colourless
V = 1393.7 (3) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2093 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
thin–slice ω scansh = 1515
5910 measured reflectionsk = 109
2726 independent reflectionsl = 918
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0826P)2]
where P = (Fo2 + 2Fc2)/3
2726 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.29 e Å3
1 restraintΔρmin = 0.23 e Å3
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.

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 > σ(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*/Ueq
S10.79823 (4)0.29302 (6)0.16341 (4)0.0561 (2)
O10.82928 (17)0.21998 (19)0.08862 (14)0.0823 (5)
O20.87297 (14)0.25233 (18)0.26341 (13)0.0740 (5)
O30.50148 (12)0.4078 (2)0.11922 (13)0.0800 (5)
N10.66473 (16)0.2577 (2)0.14401 (15)0.0625 (5)
N20.31132 (14)0.2555 (2)0.11152 (11)0.0479 (4)
C10.78682 (15)0.5064 (2)0.14980 (13)0.0461 (4)
C20.86928 (18)0.6217 (3)0.15757 (14)0.0569 (5)
H20.94540.59370.16890.068*
C30.8328 (2)0.7824 (3)0.14758 (16)0.0658 (6)
H30.88560.86420.15190.079*
C40.7210 (2)0.8221 (3)0.13156 (16)0.0671 (6)
H40.69930.93060.12580.080*
C50.6396 (2)0.7047 (2)0.12369 (16)0.0601 (6)
H50.56340.73260.11210.072*
C60.67428 (15)0.5442 (2)0.13346 (12)0.0461 (4)
C70.60497 (17)0.3956 (2)0.13099 (15)0.0552 (5)
C80.22973 (19)0.3617 (3)0.10856 (14)0.0574 (5)
C90.1236 (2)0.2999 (4)0.10037 (18)0.0763 (7)
H90.06390.36940.09760.092*
C100.1073 (2)0.1357 (4)0.09644 (19)0.0846 (8)
H100.03630.09400.09170.102*
C110.1927 (2)0.0329 (3)0.09936 (17)0.0759 (7)
H110.18030.07840.09610.091*
C120.29770 (19)0.0937 (3)0.10710 (14)0.0573 (5)
C130.2598 (2)0.5362 (3)0.1168 (2)0.0832 (8)
H13A0.31020.56120.18420.125*
H13B0.18990.59960.09750.125*
H13C0.29870.56110.07400.125*
C140.3975 (2)0.0086 (3)0.1122 (2)0.0815 (7)
H14A0.45930.05960.11160.122*
H14B0.37300.08010.05610.122*
H14C0.42470.07120.17230.122*
H10.3761 (12)0.291 (3)0.1160 (17)0.066 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0516 (3)0.0394 (3)0.0812 (4)0.0033 (2)0.0309 (3)0.0008 (2)
O10.0982 (13)0.0554 (10)0.1132 (14)0.0063 (9)0.0634 (12)0.0138 (8)
O20.0576 (9)0.0664 (10)0.0950 (12)0.0161 (8)0.0275 (9)0.0202 (8)
O30.0418 (8)0.0821 (12)0.1161 (13)0.0090 (8)0.0320 (8)0.0028 (10)
N10.0569 (11)0.0414 (9)0.0887 (13)0.0085 (8)0.0287 (10)0.0032 (8)
N20.0427 (8)0.0526 (10)0.0491 (9)0.0029 (8)0.0192 (7)0.0023 (7)
C10.0464 (10)0.0396 (10)0.0529 (10)0.0035 (8)0.0208 (8)0.0025 (8)
C20.0521 (11)0.0554 (13)0.0657 (12)0.0148 (9)0.0262 (9)0.0075 (9)
C30.0828 (16)0.0501 (13)0.0650 (13)0.0223 (12)0.0302 (12)0.0065 (10)
C40.0951 (17)0.0341 (11)0.0662 (13)0.0010 (11)0.0263 (12)0.0016 (9)
C50.0610 (12)0.0483 (12)0.0674 (13)0.0102 (10)0.0220 (10)0.0006 (9)
C60.0444 (9)0.0411 (10)0.0517 (10)0.0000 (8)0.0183 (8)0.0021 (7)
C70.0434 (10)0.0528 (12)0.0678 (12)0.0057 (9)0.0207 (9)0.0009 (9)
C80.0566 (11)0.0678 (14)0.0510 (11)0.0057 (11)0.0249 (9)0.0060 (9)
C90.0543 (13)0.113 (2)0.0696 (15)0.0061 (14)0.0333 (11)0.0116 (13)
C100.0642 (15)0.120 (2)0.0796 (16)0.0339 (16)0.0388 (13)0.0200 (15)
C110.0842 (17)0.0753 (17)0.0738 (15)0.0288 (15)0.0377 (13)0.0074 (12)
C120.0638 (12)0.0531 (12)0.0529 (11)0.0071 (10)0.0212 (9)0.0011 (9)
C130.0940 (19)0.0629 (16)0.1000 (18)0.0117 (14)0.0467 (15)0.0113 (13)
C140.0858 (18)0.0565 (15)0.0968 (17)0.0138 (13)0.0311 (14)0.0073 (13)
Geometric parameters (Å, º) top
S1—O21.4309 (17)C5—H50.9300
S1—O11.4385 (17)C6—C71.495 (3)
S1—N11.6073 (19)C8—C91.385 (3)
S1—C11.771 (2)C8—C131.481 (3)
O3—C71.242 (3)C9—C101.368 (4)
N1—C71.333 (3)C9—H90.9300
N2—C81.335 (3)C10—C111.354 (4)
N2—C121.344 (3)C10—H100.9300
N2—H10.840 (10)C11—C121.370 (3)
C1—C61.369 (3)C11—H110.9300
C1—C21.376 (3)C12—C141.486 (3)
C2—C31.391 (3)C13—H13A0.9600
C2—H20.9300C13—H13B0.9600
C3—C41.365 (3)C13—H13C0.9600
C3—H30.9300C14—H14A0.9600
C4—C51.378 (3)C14—H14B0.9600
C4—H40.9300C14—H14C0.9600
C5—C61.383 (3)
O2—S1—O1114.91 (11)O3—C7—C6120.09 (19)
O2—S1—N1110.20 (10)N1—C7—C6114.14 (17)
O1—S1—N1111.74 (11)N2—C8—C9117.3 (2)
O2—S1—C1109.83 (9)N2—C8—C13118.0 (2)
O1—S1—C1111.37 (9)C9—C8—C13124.7 (2)
N1—S1—C197.42 (9)C10—C9—C8119.4 (2)
C7—N1—S1110.84 (14)C10—C9—H9120.3
C8—N2—C12124.77 (19)C8—C9—H9120.3
C8—N2—H1118.6 (16)C11—C10—C9121.1 (2)
C12—N2—H1116.6 (16)C11—C10—H10119.5
C6—C1—C2122.97 (19)C9—C10—H10119.5
C6—C1—S1106.09 (14)C10—C11—C12119.7 (2)
C2—C1—S1130.87 (16)C10—C11—H11120.2
C1—C2—C3116.5 (2)C12—C11—H11120.2
C1—C2—H2121.7N2—C12—C11117.8 (2)
C3—C2—H2121.7N2—C12—C14118.3 (2)
C4—C3—C2121.2 (2)C11—C12—C14123.9 (2)
C4—C3—H3119.4C8—C13—H13A109.5
C2—C3—H3119.4C8—C13—H13B109.5
C3—C4—C5121.4 (2)H13A—C13—H13B109.5
C3—C4—H4119.3C8—C13—H13C109.5
C5—C4—H4119.3H13A—C13—H13C109.5
C4—C5—C6118.3 (2)H13B—C13—H13C109.5
C4—C5—H5120.9C12—C14—H14A109.5
C6—C5—H5120.9C12—C14—H14B109.5
C1—C6—C5119.69 (18)H14A—C14—H14B109.5
C1—C6—C7111.43 (16)C12—C14—H14C109.5
C5—C6—C7128.87 (19)H14A—C14—H14C109.5
O3—C7—N1125.8 (2)H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O30.84 (1)1.83 (1)2.657 (2)168 (2)
 

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