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The asymmetric unit of the title compound, C2H8N+·C7H4NO3S, contains a saccharinate anion and a protonated ethyl­amine cation. Inter­molecular N—H...O hydrogen bonds link these ions into a two-dimensional framework structure. The crystal packing is further stabilized by weak inter­molecular C—H...O hydrogen bonds

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012116/cv2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012116/cv2024Isup2.hkl
Contains datablock I

CCDC reference: 608409

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.113
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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: SMART; data reduction: SAINT-Plus (Bruker, 2001); 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.

Ethylammonium saccharinate top
Crystal data top
C2H8N+·C7H4NO3SF(000) = 480
Mr = 228.27Dx = 1.434 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3388 reflections
a = 9.6355 (9) Åθ = 2.8–28.2°
b = 11.2251 (10) ŵ = 0.30 mm1
c = 10.5563 (10) ÅT = 292 K
β = 112.138 (1)°Prism, colourless
V = 1057.59 (17) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2276 independent reflections
Radiation source: fine-focus sealed tube2047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
0.3° wide ω exposures scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 128
Tmin = 0.943, Tmax = 0.944k = 1414
5187 measured reflectionsl = 1311
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1108P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2276 reflectionsΔρmax = 0.29 e Å3
139 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.039 (5)
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
S10.95159 (4)0.22421 (3)0.61827 (4)0.03556 (17)
N10.87219 (15)0.32116 (14)0.50235 (13)0.0459 (4)
N20.75630 (15)1.01716 (13)0.27650 (14)0.0457 (3)
H2A0.72851.09330.26380.069*
H2B0.78380.99320.20900.069*
H2C0.83301.00930.35610.069*
O10.94215 (13)0.10551 (11)0.56239 (13)0.0520 (3)
O21.10321 (12)0.25868 (11)0.70113 (13)0.0479 (3)
O30.67492 (12)0.45145 (10)0.44733 (11)0.0448 (3)
C10.83332 (16)0.23923 (13)0.71121 (15)0.0334 (3)
C20.83629 (18)0.18393 (14)0.82944 (15)0.0412 (4)
H20.90810.12690.87410.049*
C30.7276 (2)0.21744 (15)0.87769 (19)0.0503 (4)
H30.72580.18210.95670.060*
C40.6205 (2)0.30305 (17)0.81068 (19)0.0497 (4)
H40.54890.32430.84600.060*
C50.61892 (18)0.35709 (14)0.69198 (17)0.0419 (4)
H50.54680.41370.64660.050*
C60.72783 (15)0.32430 (12)0.64324 (14)0.0335 (3)
C70.75423 (16)0.37194 (13)0.52079 (14)0.0363 (3)
C80.5764 (2)0.9804 (2)0.3872 (2)0.0655 (6)
H8A0.65800.97550.47430.098*
H8B0.49700.92850.38690.098*
H8C0.54021.06080.37140.098*
C90.6290 (2)0.94356 (19)0.2774 (2)0.0591 (5)
H9A0.65950.86070.29050.071*
H9B0.54680.95040.18940.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0313 (2)0.0394 (3)0.0357 (2)0.00459 (13)0.01232 (17)0.00329 (13)
N10.0422 (7)0.0599 (9)0.0400 (7)0.0126 (6)0.0207 (6)0.0114 (6)
N20.0423 (7)0.0540 (8)0.0421 (7)0.0042 (6)0.0173 (6)0.0023 (6)
O10.0517 (7)0.0497 (7)0.0529 (7)0.0076 (5)0.0178 (6)0.0167 (6)
O20.0305 (6)0.0530 (7)0.0557 (7)0.0007 (5)0.0114 (5)0.0017 (5)
O30.0432 (6)0.0473 (6)0.0450 (6)0.0099 (5)0.0178 (5)0.0138 (5)
C10.0323 (7)0.0329 (7)0.0345 (7)0.0018 (5)0.0122 (6)0.0021 (5)
C20.0449 (8)0.0393 (8)0.0384 (8)0.0059 (6)0.0147 (6)0.0056 (6)
C30.0601 (11)0.0521 (10)0.0445 (9)0.0054 (8)0.0264 (8)0.0105 (7)
C40.0508 (10)0.0547 (9)0.0550 (10)0.0086 (8)0.0330 (8)0.0042 (8)
C50.0399 (8)0.0412 (8)0.0485 (8)0.0089 (6)0.0211 (7)0.0054 (6)
C60.0338 (7)0.0325 (7)0.0347 (7)0.0021 (5)0.0133 (6)0.0002 (5)
C70.0340 (7)0.0402 (7)0.0342 (7)0.0015 (6)0.0123 (6)0.0027 (6)
C80.0716 (13)0.0733 (14)0.0664 (13)0.0048 (10)0.0427 (11)0.0003 (10)
C90.0548 (10)0.0651 (12)0.0684 (12)0.0057 (9)0.0358 (9)0.0117 (10)
Geometric parameters (Å, º) top
S1—O21.4443 (12)C3—C41.393 (2)
S1—O11.4460 (12)C3—H30.9300
S1—N11.6005 (14)C4—C51.387 (2)
S1—C11.7698 (15)C4—H40.9300
N1—C71.3495 (19)C5—C61.381 (2)
N2—C91.482 (2)C5—H50.9300
N2—H2A0.8900C6—C71.5065 (19)
N2—H2B0.8900C8—C91.488 (2)
N2—H2C0.8900C8—H8A0.9600
O3—C71.2391 (17)C8—H8B0.9600
C1—C61.3820 (19)C8—H8C0.9600
C1—C21.384 (2)C9—H9A0.9700
C2—C31.378 (2)C9—H9B0.9700
C2—H20.9300
O2—S1—O1112.81 (7)C5—C4—H4119.5
O2—S1—N1111.33 (8)C3—C4—H4119.5
O1—S1—N1112.10 (8)C6—C5—C4117.96 (14)
O2—S1—C1110.76 (7)C6—C5—H5121.0
O1—S1—C1111.06 (7)C4—C5—H5121.0
N1—S1—C197.87 (7)C5—C6—C1120.27 (14)
C7—N1—S1111.27 (10)C5—C6—C7128.50 (13)
C9—N2—H2A109.5C1—C6—C7111.21 (12)
C9—N2—H2B109.5O3—C7—N1124.63 (14)
H2A—N2—H2B109.5O3—C7—C6121.93 (13)
C9—N2—H2C109.5N1—C7—C6113.42 (12)
H2A—N2—H2C109.5C9—C8—H8A109.5
H2B—N2—H2C109.5C9—C8—H8B109.5
C6—C1—C2122.62 (14)H8A—C8—H8B109.5
C6—C1—S1106.22 (11)C9—C8—H8C109.5
C2—C1—S1131.15 (12)H8A—C8—H8C109.5
C3—C2—C1116.76 (15)H8B—C8—H8C109.5
C3—C2—H2121.6N2—C9—C8112.08 (17)
C1—C2—H2121.6N2—C9—H9A109.2
C2—C3—C4121.44 (16)C8—C9—H9A109.2
C2—C3—H3119.3N2—C9—H9B109.2
C4—C3—H3119.3C8—C9—H9B109.2
C5—C4—C3120.94 (16)H9A—C9—H9B107.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2C···O1i0.892.393.0833 (18)136
N2—H2C···O1ii0.892.303.0373 (18)140
N2—H2B···O3iii0.891.902.7832 (17)174
N2—H2A···O2iv0.892.012.8733 (19)162
C2—H2···O3v0.932.553.383 (2)150
C5—H5···O3vi0.932.503.415 (2)168
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+1, z; (iii) x+3/2, y+1/2, z+1/2; (iv) x1/2, y+3/2, z1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x+1, y+1, z+1.
 

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