Buy article online - an online subscription or single-article purchase is required to access this article.
organic compounds
In the title compound, C2H10N22+·2C7H5O3S-·4H2O, the cation and anion interact with the water molecules to form a three-dimensional network. In the anion, the negative charge resides on the sulfonate group. The dication lies on a special position of site symmetry .
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027278/cv6403sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027278/cv6403Isup2.hkl |
CCDC reference: 259102
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.143
- Data-to-parameter ratio = 14.0
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 ............ 2.00 Ratio PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 613.10 Ang-3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for S1 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7 PLAT736_ALERT_1_C H...A Calc 1.933(14), Rep 1.93(3) ...... 2.14 su-Rat H5# -O1 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Ethylenediammonium bis(3-carboxy-4-hydroxybenzenesulfonate) tetrahydrate top
Crystal data top
C2H10N22+·2C7H5O6S−·4H2O | Z = 1 |
Mr = 568.52 | F(000) = 298 |
Triclinic, P1 | Dx = 1.540 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.111 (1) Å | Cell parameters from 5480 reflections |
b = 7.140 (1) Å | θ = 3.0–27.5° |
c = 12.765 (3) Å | µ = 0.30 mm−1 |
α = 87.77 (3)° | T = 295 K |
β = 75.86 (3)° | Prism, colorless |
γ = 77.36 (3)° | 0.39 × 0.26 × 0.19 mm |
V = 613.1 (2) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2793 independent reflections |
Radiation source: fine-focus sealed tube | 2394 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→8 |
Tmin = 0.841, Tmax = 0.946 | k = −9→9 |
6115 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0958P)2 + 0.0909P] where P = (Fo2 + 2Fc2)/3 |
2793 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.47 e Å−3 |
14 restraints | Δρmin = −0.44 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.53181 (7) | 0.68846 (6) | 0.66233 (3) | 0.0386 (2) | |
O1 | 0.6570 (3) | 0.5202 (3) | 0.6029 (1) | 0.0665 (5) | |
O2 | 0.3222 (2) | 0.6851 (2) | 0.6885 (1) | 0.0519 (4) | |
O3 | 0.5682 (3) | 0.8604 (3) | 0.6045 (2) | 0.0671 (5) | |
O4 | 0.3808 (2) | 0.8092 (3) | 1.1669 (1) | 0.0541 (4) | |
O5 | 0.1635 (2) | 0.8473 (3) | 1.0641 (1) | 0.0509 (4) | |
O6 | 0.7569 (2) | 0.7011 (3) | 1.0755 (1) | 0.0630 (5) | |
O1w | 1.0837 (2) | 0.0599 (2) | 0.7438 (1) | 0.0503 (4) | |
O2w | 0.2677 (6) | 0.3189 (5) | 0.6337 (2) | 0.112 (1) | |
N1 | 0.7954 (3) | 0.1292 (3) | 0.6119 (1) | 0.0452 (4) | |
C1 | 0.5976 (3) | 0.6937 (2) | 0.7865 (1) | 0.0347 (4) | |
C2 | 0.4510 (2) | 0.7458 (2) | 0.8799 (1) | 0.0341 (4) | |
C3 | 0.5005 (3) | 0.7513 (2) | 0.9785 (1) | 0.0347 (4) | |
C4 | 0.7001 (3) | 0.7019 (3) | 0.9825 (2) | 0.0427 (4) | |
C5 | 0.8477 (3) | 0.6500 (3) | 0.8875 (2) | 0.0518 (5) | |
C6 | 0.7963 (3) | 0.6459 (3) | 0.7907 (2) | 0.0461 (5) | |
C7 | 0.3440 (3) | 0.8051 (3) | 1.0787 (1) | 0.0386 (4) | |
C8 | 0.9401 (3) | 0.1023 (3) | 0.5061 (1) | 0.0403 (4) | |
H5o | 0.082 (3) | 0.864 (4) | 1.127 (1) | 0.07 (1)* | |
H6o | 0.651 (4) | 0.746 (5) | 1.123 (2) | 0.11 (1)* | |
H1w1 | 1.150 (4) | 0.143 (3) | 0.721 (3) | 0.09 (1)* | |
H1w2 | 1.155 (3) | −0.053 (2) | 0.731 (2) | 0.07 (1)* | |
H2w1 | 0.241 (7) | 0.438 (2) | 0.645 (3) | 0.15 (2)* | |
H2w2 | 0.337 (6) | 0.293 (5) | 0.570 (2) | 0.14 (2)* | |
H1n1 | 0.734 (3) | 0.246 (2) | 0.620 (2) | 0.07 (1)* | |
H1n2 | 0.858 (4) | 0.100 (3) | 0.661 (2) | 0.10 (1)* | |
H1n3 | 0.712 (3) | 0.057 (3) | 0.617 (2) | 0.07 (1)* | |
H2 | 0.3184 | 0.7773 | 0.8769 | 0.041* | |
H5 | 0.9807 | 0.6183 | 0.8898 | 0.062* | |
H6 | 0.8948 | 0.6109 | 0.7276 | 0.055* | |
H8a | 1.0283 | 0.1904 | 0.5003 | 0.048* | |
H8b | 0.8706 | 0.1299 | 0.4488 | 0.048* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0390 (3) | 0.0378 (3) | 0.0332 (3) | −0.0011 (2) | −0.0038 (2) | −0.0017 (2) |
O1 | 0.073 (1) | 0.064 (1) | 0.046 (1) | 0.019 (1) | −0.011 (1) | −0.020 (1) |
O2 | 0.043 (1) | 0.067 (1) | 0.044 (1) | −0.011 (1) | −0.008 (1) | −0.009 (1) |
O3 | 0.082 (1) | 0.068 (1) | 0.059 (1) | −0.029 (1) | −0.024 (1) | 0.026 (1) |
O4 | 0.049 (1) | 0.077 (1) | 0.034 (1) | −0.009 (1) | −0.008 (1) | −0.002 (1) |
O5 | 0.034 (1) | 0.075 (1) | 0.037 (1) | −0.003 (1) | −0.002 (1) | −0.004 (1) |
O6 | 0.044 (1) | 0.099 (1) | 0.048 (1) | −0.009 (1) | −0.019 (1) | 0.001 (1) |
O1w | 0.039 (1) | 0.063 (1) | 0.043 (1) | −0.004 (1) | −0.003 (1) | −0.009 (1) |
O2w | 0.167 (3) | 0.119 (2) | 0.057 (1) | −0.094 (2) | 0.015 (1) | −0.017 (1) |
N1 | 0.045 (1) | 0.046 (1) | 0.037 (1) | 0.000 (1) | −0.002 (1) | −0.009 (1) |
C1 | 0.034 (1) | 0.033 (1) | 0.034 (1) | −0.003 (1) | −0.005 (1) | 0.000 (1) |
C2 | 0.029 (1) | 0.034 (1) | 0.036 (1) | −0.004 (1) | −0.005 (1) | 0.000 (1) |
C3 | 0.032 (1) | 0.035 (1) | 0.035 (1) | −0.005 (1) | −0.006 (1) | 0.002 (1) |
C4 | 0.036 (1) | 0.049 (1) | 0.043 (1) | −0.008 (1) | −0.012 (1) | 0.003 (1) |
C5 | 0.029 (1) | 0.066 (1) | 0.056 (1) | −0.002 (1) | −0.009 (1) | 0.001 (1) |
C6 | 0.032 (1) | 0.052 (1) | 0.045 (1) | −0.001 (1) | 0.000 (1) | −0.003 (1) |
C7 | 0.038 (1) | 0.040 (1) | 0.035 (1) | −0.008 (1) | −0.005 (1) | 0.001 (1) |
C8 | 0.045 (1) | 0.039 (1) | 0.031 (1) | 0.000 (1) | −0.005 (1) | −0.004 (1) |
Geometric parameters (Å, º) top
S1—O1 | 1.444 (2) | C8—C8i | 1.514 (4) |
S1—O2 | 1.451 (2) | O5—H5o | 0.86 (3) |
S1—O3 | 1.447 (2) | O6—H6o | 0.85 (3) |
S1—C1 | 1.763 (2) | O1w—H1w1 | 0.84 (3) |
O4—C7 | 1.218 (2) | O1w—H1w2 | 0.85 (3) |
O5—C7 | 1.310 (2) | O2w—H2w1 | 0.84 (3) |
O6—C4 | 1.342 (3) | O2w—H2w2 | 0.84 (3) |
N1—C8 | 1.475 (2) | N1—H1n1 | 0.85 (3) |
C1—C2 | 1.379 (2) | N1—H1n2 | 0.85 (3) |
C1—C6 | 1.392 (3) | N1—H1n3 | 0.86 (3) |
C2—C3 | 1.392 (2) | C2—H2 | 0.9300 |
C3—C4 | 1.399 (3) | C5—H5 | 0.9300 |
C3—C7 | 1.476 (2) | C6—H6 | 0.9300 |
C4—C5 | 1.397 (3) | C8—H8a | 0.9700 |
C5—C6 | 1.375 (3) | C8—H8b | 0.9700 |
O1—S1—O2 | 113.4 (1) | C7—O5—H5o | 108 (2) |
O1—S1—O3 | 110.3 (1) | C4—O6—H6o | 105 (3) |
O1—S1—C1 | 107.5 (1) | H1w1—O1w—H1w2 | 111 (2) |
O2—S1—O3 | 111.1 (1) | H2w1—O2w—H2w2 | 110 (2) |
O2—S1—C1 | 106.4 (1) | C8—N1—H1n1 | 109 (2) |
O3—S1—C1 | 107.9 (1) | C8—N1—H1n2 | 109 (2) |
C2—C1—C6 | 120.0 (2) | H1n1—N1—H1n2 | 110 (2) |
C2—C1—S1 | 119.6 (1) | C8—N1—H1n3 | 111 (2) |
C6—C1—S1 | 120.4 (1) | H1n1—N1—H1n3 | 109 (1) |
C1—C2—C3 | 120.3 (2) | H1n2—N1—H1n3 | 109 (1) |
C2—C3—C4 | 119.5 (2) | C1—C2—H2 | 119.8 |
C2—C3—C7 | 120.5 (2) | C3—C2—H2 | 119.8 |
C4—C3—C7 | 120.0 (2) | C6—C5—H5 | 120.0 |
O6—C4—C3 | 122.3 (2) | C4—C5—H5 | 120.0 |
O6—C4—C5 | 118.0 (2) | C5—C6—H6 | 119.8 |
C3—C4—C5 | 119.8 (2) | C1—C6—H6 | 119.8 |
C4—C5—C6 | 120.0 (2) | N1—C8—H8a | 109.7 |
C1—C6—C5 | 120.4 (2) | C8i—C8—H8a | 109.7 |
O4—C7—O5 | 123.4 (2) | N1—C8—H8b | 109.7 |
O4—C7—C3 | 122.6 (2) | C8i—C8—H8b | 109.7 |
O5—C7—C3 | 114.0 (2) | H8a—C8—H8b | 108.2 |
N1—C8—C8i | 109.9 (2) | ||
O1—S1—C1—C2 | −139.3 (2) | C2—C3—C4—C5 | 0.8 (3) |
O3—S1—C1—C2 | 101.8 (2) | C7—C3—C4—C5 | 179.6 (2) |
O2—S1—C1—C2 | −17.5 (2) | O6—C4—C5—C6 | 179.0 (2) |
O1—S1—C1—C6 | 40.8 (2) | C3—C4—C5—C6 | −0.6 (3) |
O3—S1—C1—C6 | −78.1 (2) | C4—C5—C6—C1 | 0.2 (3) |
O2—S1—C1—C6 | 162.6 (2) | C2—C1—C6—C5 | 0.1 (3) |
C6—C1—C2—C3 | 0.1 (3) | S1—C1—C6—C5 | 180.0 (2) |
S1—C1—C2—C3 | −179.8 (1) | C2—C3—C7—O4 | 179.0 (2) |
C1—C2—C3—C4 | −0.6 (3) | C4—C3—C7—O4 | 0.2 (3) |
C1—C2—C3—C7 | −179.4 (2) | C2—C3—C7—O5 | −0.9 (3) |
C2—C3—C4—O6 | −178.8 (2) | C4—C3—C7—O5 | −179.7 (2) |
C7—C3—C4—O6 | 0.1 (3) |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O1 | 0.85 (3) | 1.93 (3) | 2.758 (3) | 163 (3) |
N1—H1n3···O3ii | 0.86 (3) | 1.94 (3) | 2.784 (3) | 167 (2) |
N1—H1n2···O1w | 0.85 (3) | 2.09 (3) | 2.908 (3) | 161 (3) |
O5—H5o···O1wiii | 0.86 (2) | 1.81 (3) | 2.656 (2) | 170 (3) |
O6—H6o···O4 | 0.85 (3) | 1.82 (2) | 2.598 (2) | 151 (4) |
O1w—H1w1···O2wiv | 0.84 (3) | 1.85 (3) | 2.658 (3) | 163 (4) |
O1w—H1w2···O2v | 0.85 (3) | 2.00 (3) | 2.848 (3) | 175 (3) |
O2w—H2w1···O2 | 0.84 (3) | 2.10 (3) | 2.863 (3) | 150 (5) |
O2w—H2w2···O3vi | 0.85 (2) | 2.40 (2) | 3.188 (3) | 156 (4) |
Symmetry codes: (ii) x, y−1, z; (iii) −x+1, −y+1, −z+2; (iv) x+1, y, z; (v) x+1, y−1, z; (vi) −x+1, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register