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The asymmetric unit of the title compound, C2H10N22+·2C7H4NO3S, is composed of two saccharinate anions and one doubly protonated ethylene­diamine cation. These are linked by N—H...O and N—H...N hydrogen bonds and aromatic π–π stacking inter­actions, leading to a two-dimensional framework structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005046/rz6171sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005046/rz6171Isup2.hkl
Contains datablock I

CCDC reference: 601238

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.122
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C15 .. 2.93 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C16 .. 2.97 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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.

Ethylenediammonium disaccharinate top
Crystal data top
C2H10N22+·2C7H4NO3SZ = 2
Mr = 426.46F(000) = 444
Triclinic, P1Dx = 1.522 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3344 (9) ÅCell parameters from 2723 reflections
b = 10.0494 (12) Åθ = 2.5–28.2°
c = 13.2454 (16) ŵ = 0.33 mm1
α = 84.741 (2)°T = 292 K
β = 86.943 (2)°Needle, colourless
γ = 73.305 (2)°0.40 × 0.20 × 0.10 mm
V = 930.8 (2) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3612 independent reflections
Radiation source: fine-focus sealed tube2944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
0.3° wide ω exposures scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 89
Tmin = 0.880, Tmax = 0.968k = 1212
7288 measured reflectionsl = 1616
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.2579P]
where P = (Fo2 + 2Fc2)/3
3612 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.28 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
S10.26054 (9)0.42458 (7)0.69397 (4)0.04556 (19)
S20.48411 (9)0.06234 (6)0.13583 (4)0.04499 (19)
N10.2815 (3)0.4573 (2)0.80964 (13)0.0428 (5)
N20.3586 (3)0.20223 (19)0.07813 (13)0.0393 (4)
N30.3815 (3)0.6931 (2)0.08137 (14)0.0438 (5)
H3A0.35330.64610.03360.066*
H3B0.48940.64310.11020.066*
H3C0.39560.77370.05360.066*
N40.0543 (3)0.7217 (2)0.06211 (14)0.0452 (5)
H4A0.02540.67600.01550.068*
H4B0.15730.77780.03220.068*
H4C0.08830.66090.10680.068*
O10.1359 (3)0.3377 (2)0.69091 (14)0.0662 (5)
O20.4447 (3)0.3753 (2)0.64614 (13)0.0639 (5)
O30.2158 (2)0.64616 (19)0.90294 (12)0.0527 (4)
O40.3861 (4)0.0425 (2)0.14816 (16)0.0822 (7)
O50.6700 (3)0.0211 (2)0.08873 (15)0.0777 (6)
O60.2165 (3)0.42760 (17)0.11134 (13)0.0628 (5)
C10.1436 (3)0.5968 (3)0.64886 (17)0.0440 (6)
C20.0775 (4)0.6506 (3)0.55359 (19)0.0614 (8)
H20.09620.59490.49940.074*
C30.0175 (4)0.7907 (4)0.5427 (2)0.0765 (10)
H30.06590.83030.47990.092*
C40.0425 (4)0.8732 (3)0.6223 (3)0.0732 (9)
H40.10790.96730.61250.088*
C50.0284 (4)0.8187 (3)0.7177 (2)0.0560 (7)
H50.01320.87490.77130.067*
C60.1216 (3)0.6784 (3)0.72950 (17)0.0423 (5)
C70.2097 (3)0.5940 (3)0.82257 (16)0.0401 (5)
C80.4929 (3)0.1296 (2)0.25307 (16)0.0375 (5)
C90.5735 (4)0.0645 (3)0.34250 (19)0.0530 (6)
H90.63750.03020.34860.064*
C100.5551 (4)0.1461 (3)0.42258 (18)0.0583 (7)
H100.60730.10570.48440.070*
C110.4611 (4)0.2861 (3)0.41301 (18)0.0552 (7)
H110.45360.33920.46780.066*
C120.3770 (4)0.3495 (3)0.32259 (16)0.0458 (6)
H120.31130.44380.31660.055*
C130.3938 (3)0.2690 (2)0.24250 (15)0.0334 (5)
C140.3136 (3)0.3098 (2)0.13856 (16)0.0382 (5)
C150.2265 (3)0.7201 (2)0.15874 (16)0.0381 (5)
H15A0.25980.76850.21190.046*
H15B0.21200.63200.18910.046*
C160.0414 (3)0.8057 (2)0.11504 (19)0.0458 (6)
H16A0.04240.84950.16920.055*
H16B0.06440.87900.06760.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0503 (4)0.0564 (4)0.0319 (3)0.0171 (3)0.0015 (2)0.0073 (3)
S20.0562 (4)0.0303 (3)0.0449 (3)0.0037 (3)0.0097 (3)0.0080 (2)
N10.0457 (11)0.0495 (12)0.0284 (9)0.0056 (9)0.0037 (8)0.0017 (8)
N20.0484 (11)0.0351 (10)0.0349 (9)0.0099 (8)0.0097 (8)0.0061 (8)
N30.0385 (10)0.0470 (11)0.0467 (11)0.0106 (9)0.0081 (8)0.0088 (9)
N40.0359 (10)0.0558 (12)0.0420 (10)0.0102 (9)0.0046 (8)0.0013 (9)
O10.0814 (14)0.0682 (13)0.0603 (11)0.0381 (11)0.0074 (10)0.0056 (9)
O20.0592 (11)0.0813 (14)0.0485 (10)0.0122 (10)0.0091 (9)0.0232 (9)
O30.0608 (11)0.0653 (12)0.0356 (9)0.0212 (9)0.0018 (8)0.0143 (8)
O40.144 (2)0.0432 (11)0.0753 (13)0.0483 (13)0.0254 (13)0.0014 (10)
O50.0615 (12)0.0836 (15)0.0677 (13)0.0193 (11)0.0024 (10)0.0305 (11)
O60.0904 (14)0.0326 (9)0.0540 (10)0.0026 (9)0.0189 (10)0.0008 (8)
C10.0383 (12)0.0627 (16)0.0355 (11)0.0230 (12)0.0055 (9)0.0041 (10)
C20.0628 (17)0.091 (2)0.0406 (13)0.0411 (17)0.0154 (12)0.0147 (14)
C30.0647 (19)0.104 (3)0.066 (2)0.0424 (19)0.0299 (16)0.0409 (19)
C40.0499 (16)0.0627 (19)0.102 (3)0.0179 (14)0.0157 (16)0.0344 (18)
C50.0441 (14)0.0513 (16)0.0707 (18)0.0140 (12)0.0019 (12)0.0066 (13)
C60.0344 (12)0.0528 (14)0.0411 (12)0.0170 (11)0.0012 (9)0.0043 (10)
C70.0354 (12)0.0532 (14)0.0326 (11)0.0146 (11)0.0016 (9)0.0027 (10)
C80.0384 (12)0.0389 (12)0.0351 (11)0.0112 (10)0.0042 (9)0.0003 (9)
C90.0486 (14)0.0592 (16)0.0475 (14)0.0119 (12)0.0114 (11)0.0101 (12)
C100.0536 (15)0.092 (2)0.0330 (12)0.0296 (15)0.0118 (11)0.0122 (13)
C110.0610 (16)0.084 (2)0.0322 (12)0.0362 (16)0.0036 (11)0.0139 (12)
C120.0574 (15)0.0482 (14)0.0367 (12)0.0215 (12)0.0058 (10)0.0107 (10)
C130.0380 (11)0.0364 (12)0.0294 (10)0.0164 (9)0.0010 (8)0.0028 (8)
C140.0460 (13)0.0338 (12)0.0354 (11)0.0121 (10)0.0050 (9)0.0007 (9)
C150.0433 (12)0.0353 (12)0.0369 (11)0.0124 (10)0.0049 (9)0.0035 (9)
C160.0432 (13)0.0364 (13)0.0545 (14)0.0052 (10)0.0007 (11)0.0077 (11)
Geometric parameters (Å, º) top
S1—O21.4325 (19)C3—C41.374 (5)
S1—O11.4385 (19)C3—H30.9300
S1—N11.6201 (18)C4—C51.395 (4)
S1—C11.761 (3)C4—H40.9300
S2—O41.430 (2)C5—C61.377 (3)
S2—O51.432 (2)C5—H50.9300
S2—N21.5945 (19)C6—C71.495 (3)
S2—C81.761 (2)C8—C91.375 (3)
N1—C71.347 (3)C8—C131.378 (3)
N2—C141.358 (3)C9—C101.377 (4)
N3—C151.471 (3)C9—H90.9300
N3—H3A0.8900C10—C111.375 (4)
N3—H3B0.8900C10—H100.9300
N3—H3C0.8900C11—C121.390 (4)
N4—C161.482 (3)C11—H110.9300
N4—H4A0.8900C12—C131.372 (3)
N4—H4B0.8900C12—H120.9300
N4—H4C0.8900C13—C141.502 (3)
O3—C71.237 (3)C15—C161.497 (3)
O6—C141.226 (3)C15—H15A0.9700
C1—C61.381 (3)C15—H15B0.9700
C1—C21.382 (3)C16—H16A0.9700
C2—C31.378 (5)C16—H16B0.9700
C2—H20.9300
O2—S1—O1116.04 (12)C4—C5—H5121.3
O2—S1—N1110.27 (10)C5—C6—C1120.4 (2)
O1—S1—N1110.41 (11)C5—C6—C7128.5 (2)
O2—S1—C1111.67 (12)C1—C6—C7111.1 (2)
O1—S1—C1110.07 (11)O3—C7—N1123.9 (2)
N1—S1—C196.71 (10)O3—C7—C6122.7 (2)
O4—S2—O5115.51 (14)N1—C7—C6113.34 (19)
O4—S2—N2111.62 (12)C9—C8—C13122.8 (2)
O5—S2—N2109.89 (12)C9—C8—S2130.5 (2)
O4—S2—C8110.03 (11)C13—C8—S2106.70 (15)
O5—S2—C8110.69 (11)C8—C9—C10116.8 (3)
N2—S2—C897.67 (10)C8—C9—H9121.6
C7—N1—S1111.53 (15)C10—C9—H9121.6
C14—N2—S2111.53 (15)C11—C10—C9121.3 (2)
C15—N3—H3A109.5C11—C10—H10119.3
C15—N3—H3B109.5C9—C10—H10119.3
H3A—N3—H3B109.5C10—C11—C12121.0 (2)
C15—N3—H3C109.5C10—C11—H11119.5
H3A—N3—H3C109.5C12—C11—H11119.5
H3B—N3—H3C109.5C13—C12—C11118.1 (2)
C16—N4—H4A109.5C13—C12—H12120.9
C16—N4—H4B109.5C11—C12—H12120.9
H4A—N4—H4B109.5C12—C13—C8119.9 (2)
C16—N4—H4C109.5C12—C13—C14128.9 (2)
H4A—N4—H4C109.5C8—C13—C14111.21 (18)
H4B—N4—H4C109.5O6—C14—N2123.5 (2)
C6—C1—C2122.5 (3)O6—C14—C13123.59 (19)
C6—C1—S1107.19 (16)N2—C14—C13112.86 (19)
C2—C1—S1130.3 (2)N3—C15—C16111.97 (18)
C3—C2—C1116.8 (3)N3—C15—H15A109.2
C3—C2—H2121.6C16—C15—H15A109.2
C1—C2—H2121.6N3—C15—H15B109.2
C4—C3—C2121.6 (3)C16—C15—H15B109.2
C4—C3—H3119.2H15A—C15—H15B107.9
C2—C3—H3119.2N4—C16—C15112.53 (18)
C3—C4—C5121.3 (3)N4—C16—H16A109.1
C3—C4—H4119.4C15—C16—H16A109.1
C5—C4—H4119.4N4—C16—H16B109.1
C6—C5—C4117.5 (3)C15—C16—H16B109.1
C6—C5—H5121.3H16A—C16—H16B107.8
O2—S1—N1—C7114.73 (18)C5—C6—C7—N1176.8 (2)
O1—S1—N1—C7115.72 (18)C1—C6—C7—N13.3 (3)
C1—S1—N1—C71.36 (18)O4—S2—C8—C960.8 (3)
O4—S2—N2—C14115.64 (18)O5—S2—C8—C968.1 (3)
O5—S2—N2—C14114.86 (18)N2—S2—C8—C9177.2 (2)
C8—S2—N2—C140.47 (18)O4—S2—C8—C13117.49 (17)
O2—S1—C1—C6115.56 (17)O5—S2—C8—C13113.62 (17)
O1—S1—C1—C6114.04 (17)N2—S2—C8—C131.07 (17)
N1—S1—C1—C60.59 (17)C13—C8—C9—C101.4 (4)
O2—S1—C1—C265.6 (3)S2—C8—C9—C10179.44 (19)
O1—S1—C1—C264.8 (3)C8—C9—C10—C110.3 (4)
N1—S1—C1—C2179.5 (2)C9—C10—C11—C121.6 (4)
C6—C1—C2—C31.7 (4)C10—C11—C12—C131.3 (4)
S1—C1—C2—C3177.0 (2)C11—C12—C13—C80.4 (3)
C1—C2—C3—C41.0 (4)C11—C12—C13—C14178.3 (2)
C2—C3—C4—C50.3 (4)C9—C8—C13—C121.8 (3)
C3—C4—C5—C61.0 (4)S2—C8—C13—C12179.80 (17)
C4—C5—C6—C10.4 (4)C9—C8—C13—C14177.1 (2)
C4—C5—C6—C7179.7 (2)S2—C8—C13—C141.3 (2)
C2—C1—C6—C51.1 (4)S2—N2—C14—O6179.3 (2)
S1—C1—C6—C5177.92 (18)S2—N2—C14—C130.2 (2)
C2—C1—C6—C7178.8 (2)C12—C13—C14—O60.3 (4)
S1—C1—C6—C72.2 (2)C8—C13—C14—O6178.5 (2)
S1—N1—C7—O3176.86 (18)C12—C13—C14—N2179.8 (2)
S1—N1—C7—C62.9 (2)C8—C13—C14—N21.1 (3)
C5—C6—C7—O33.5 (4)N3—C15—C16—N479.7 (2)
C1—C6—C7—O3176.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O3i0.892.052.850 (2)149
N3—H3B···N1ii0.892.002.883 (3)173
N3—H3C···N2iii0.892.493.085 (3)125
N4—H4A···O3i0.891.972.816 (2)158
N4—H4B···N2iv0.892.092.867 (2)146
N4—H4C···N1v0.892.283.124 (3)158
N3—H3C···O4vi0.892.312.886 (3)123
C11—H11···O20.932.423.280 (3)154
C15—H15B···O60.972.373.083 (3)130
C15—H15A···O4vi0.972.412.934 (3)113
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z; (iv) x, y+1, z; (v) x, y+1, z+1; (vi) x, y+1, z.
 

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