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The crystal structure of the title compound, C2H10N22+·C6H2O4S2−·2H2O, is built of ethylenediammonium dications, occupying a special position on an inversion center, thiophene-2,5-dicarboxylate dianions, in a special position on the twofold axis, and water molecules in general positions. All residues are involved in an extensive hydrogen-bonding system, which links them into a three-dimensional supramolecular arrangement.
Supporting information
CCDC reference: 613867
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.084
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.294
Value of mu given = 0.290
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1995) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
Ethylenediammonium thiophene-2,5-dicarboxylate dihydrate
top
Crystal data top
C2H10N22+·C6H2O4S2−·2H2O | F(000) = 568 |
Mr = 268.29 | Dx = 1.510 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2943 reflections |
a = 11.466 (1) Å | θ = 2.7–29.6° |
b = 11.840 (1) Å | µ = 0.29 mm−1 |
c = 10.2335 (8) Å | T = 298 K |
β = 121.865 (1)° | Block, colorless |
V = 1179.9 (2) Å3 | 0.43 × 0.41 × 0.37 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1414 independent reflections |
Radiation source: fine-focus sealed tube | 1337 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
φ and ω scans | θmax = 28.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→6 |
Tmin = 0.884, Tmax = 0.899 | k = −15→15 |
3847 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | All H-atom parameters refined |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.5722P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
1414 reflections | Δρmax = 0.35 e Å−3 |
111 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0088 (15) |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.0000 | 0.28881 (3) | 0.7500 | 0.02599 (15) | |
C1 | 0.07326 (11) | 0.38960 (9) | 0.89157 (11) | 0.0231 (2) | |
C2 | 0.15111 (11) | 0.35418 (9) | 1.05636 (12) | 0.0239 (2) | |
C3 | 0.04240 (12) | 0.49597 (10) | 0.83132 (12) | 0.0289 (3) | |
O1 | 0.13038 (10) | 0.25535 (8) | 1.08492 (10) | 0.0366 (2) | |
O2 | 0.23125 (9) | 0.42399 (7) | 1.15521 (9) | 0.0332 (2) | |
H1 | 0.0760 (16) | 0.5703 (14) | 0.8934 (19) | 0.042 (4)* | |
C4 | 0.45547 (12) | 0.48329 (9) | 0.53094 (13) | 0.0254 (2) | |
H4A | 0.5117 (16) | 0.4774 (14) | 0.6436 (19) | 0.036 (4)* | |
H4B | 0.3854 (17) | 0.5341 (14) | 0.5064 (19) | 0.036 (4)* | |
N1 | 0.39028 (11) | 0.37264 (8) | 0.46677 (12) | 0.0262 (2) | |
H1A | 0.3465 (17) | 0.3538 (14) | 0.510 (2) | 0.037 (4)* | |
H1B | 0.4557 (17) | 0.3197 (14) | 0.4876 (18) | 0.035 (4)* | |
H1C | 0.3319 (19) | 0.3786 (14) | 0.363 (2) | 0.043 (4)* | |
O3 | 0.23762 (11) | 0.15514 (9) | 0.36494 (11) | 0.0367 (2) | |
H3A | 0.254 (2) | 0.0892 (18) | 0.356 (2) | 0.054 (5)* | |
H3B | 0.209 (2) | 0.1909 (17) | 0.281 (3) | 0.060 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0316 (2) | 0.0212 (2) | 0.0181 (2) | 0.000 | 0.00825 (17) | 0.000 |
C1 | 0.0226 (5) | 0.0253 (5) | 0.0165 (5) | −0.0014 (4) | 0.0070 (4) | −0.0013 (4) |
C2 | 0.0231 (5) | 0.0262 (5) | 0.0177 (5) | 0.0003 (4) | 0.0075 (4) | 0.0009 (4) |
C3 | 0.0319 (6) | 0.0251 (5) | 0.0202 (6) | −0.0009 (4) | 0.0072 (5) | −0.0016 (4) |
O1 | 0.0399 (5) | 0.0310 (5) | 0.0245 (4) | −0.0074 (4) | 0.0073 (4) | 0.0057 (3) |
O2 | 0.0362 (5) | 0.0301 (5) | 0.0192 (4) | −0.0051 (3) | 0.0051 (3) | −0.0014 (3) |
C4 | 0.0291 (5) | 0.0245 (5) | 0.0241 (5) | −0.0034 (4) | 0.0151 (5) | −0.0034 (4) |
N1 | 0.0279 (5) | 0.0238 (5) | 0.0232 (5) | −0.0035 (4) | 0.0109 (4) | 0.0005 (4) |
O3 | 0.0526 (6) | 0.0301 (5) | 0.0288 (5) | 0.0022 (4) | 0.0225 (4) | 0.0038 (4) |
Geometric parameters (Å, º) top
S1—C1 | 1.7157 (11) | C4—C4ii | 1.511 (2) |
C1—C2 | 1.4924 (14) | C4—H4A | 0.982 (17) |
C1—C3 | 1.3643 (15) | C4—H4B | 0.926 (16) |
C2—O1 | 1.2587 (14) | N1—H1A | 0.853 (18) |
C2—O2 | 1.2528 (14) | N1—H1B | 0.912 (17) |
C3—C3i | 1.417 (2) | N1—H1C | 0.909 (19) |
C3—H1 | 1.033 (16) | O3—H3A | 0.82 (2) |
C4—N1 | 1.4792 (14) | O3—H3B | 0.85 (2) |
| | | |
C1—S1—C1i | 91.86 (7) | C4ii—C4—H4A | 109.9 (9) |
C3—C1—C2 | 128.89 (10) | N1—C4—H4B | 107.0 (10) |
C3—C1—S1 | 111.46 (8) | C4ii—C4—H4B | 113.4 (10) |
C2—C1—S1 | 119.53 (8) | H4A—C4—H4B | 107.7 (14) |
O2—C2—O1 | 125.01 (10) | C4—N1—H1A | 107.4 (11) |
O2—C2—C1 | 118.24 (10) | C4—N1—H1B | 110.1 (10) |
O1—C2—C1 | 116.75 (9) | C4—N1—H1C | 109.7 (11) |
C1—C3—C3i | 112.60 (6) | H1A—N1—H1B | 109.6 (14) |
C1—C3—H1 | 125.8 (9) | H1A—N1—H1C | 110.4 (16) |
C3i—C3—H1 | 121.6 (9) | H1B—N1—H1C | 109.5 (15) |
N1—C4—C4ii | 109.94 (11) | H3A—O3—H3B | 110 (2) |
N1—C4—H4A | 108.8 (9) | | |
| | | |
C1i—S1—C1—C3 | −0.16 (6) | C3—C1—C2—O1 | 158.08 (13) |
C1i—S1—C1—C2 | 176.25 (11) | S1—C1—C2—O1 | −17.63 (14) |
C3—C1—C2—O2 | −21.81 (18) | C2—C1—C3—C3i | −175.55 (13) |
S1—C1—C2—O2 | 162.48 (9) | S1—C1—C3—C3i | 0.44 (17) |
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···O1iii | 0.85 (2) | 1.87 (2) | 2.7223 (13) | 173 (2) |
O3—H3A···O2iv | 0.82 (2) | 1.97 (2) | 2.7818 (14) | 170 (2) |
N1—H1C···O2iii | 0.909 (19) | 1.887 (19) | 2.7788 (13) | 166.6 (16) |
N1—H1B···O1v | 0.912 (17) | 1.921 (17) | 2.7970 (14) | 160.6 (15) |
N1—H1A···O3vi | 0.853 (18) | 1.973 (18) | 2.8092 (15) | 166.3 (16) |
Symmetry codes: (iii) x, y, z−1; (iv) −x+1/2, y−1/2, −z+3/2; (v) x+1/2, −y+1/2, z−1/2; (vi) −x+1/2, −y+1/2, −z+1. |
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