The title compound, poly[[rubidium-μ-5-sulfonosalicylic acid] monohydrate], Rb
+·C
7H
5O
6S
−·H
2O, the 5-sulfosalicylic acid anion (3-carboxy-4-hydroxybenzenesulfonate) has lost the proton of —SO
3H group, but retains the usual intermolecular hydrogen bond between the phenolic and carboxylic O atoms. The Rb
+ cation is surrounded by eight O atoms. The crystal packing is stabilized by intermolecular O—H
O hydrogen bonds.
Supporting information
CCDC reference: 262225
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.007 Å
- R factor = 0.045
- wR factor = 0.141
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O7 - H2 ... ?
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.03
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT416_ALERT_2_C Short Intra D-H..H-D H2 .. H5 .. 1.92 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.67 Ratio
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.
Crystal data top
Rb+·C7H5O6S−·H2O | F(000) = 632 |
Mr = 320.66 | Dx = 2.099 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2007 reflections |
a = 11.779 (11) Å | θ = 3.3–27.7° |
b = 7.363 (7) Å | µ = 5.10 mm−1 |
c = 12.025 (11) Å | T = 273 K |
β = 103.359 (12)° | Block, colourless |
V = 1014.7 (16) Å3 | 0.45 × 0.39 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1764 independent reflections |
Radiation source: fine-focus sealed tube | 1438 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 25.0°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −14→8 |
Tmin = 0.116, Tmax = 0.542 | k = −8→8 |
4884 measured reflections | l = −13→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0973P)2 + 3.1685P] where P = (Fo2 + 2Fc2)/3 |
1766 reflections | (Δ/σ)max = 0.001 |
153 parameters | Δρmax = 1.07 e Å−3 |
3 restraints | Δρmin = −0.53 e Å−3 |
Special details top
Experimental. The chemical composition was determined by C, H, N element analysis and Rb+ by
Tas-986 atomic absorption spectrometric at a wavelength of 852.1 nm. |
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 | |
Rb1 | 0.90569 (5) | 0.57370 (8) | 0.74921 (5) | 0.0355 (3) | |
O1 | 0.1637 (3) | 0.9417 (5) | 0.5299 (3) | 0.0240 (9) | |
O2 | 0.9503 (3) | 0.3030 (5) | 0.5771 (3) | 0.0295 (9) | |
O3 | 0.0676 (4) | 0.7243 (5) | 0.6283 (3) | 0.0291 (9) | |
O4 | 0.6582 (3) | 0.5444 (5) | 0.6836 (3) | 0.0278 (9) | |
O5 | 0.5799 (3) | 0.8174 (5) | 0.6388 (3) | 0.0245 (8) | |
H5 | 0.6483 | 0.8489 | 0.6588 | 0.037* | |
O6 | 0.5239 (4) | 0.2584 (5) | 0.6404 (3) | 0.0272 (9) | |
H6 | 0.5860 | 0.3135 | 0.6577 | 0.041* | |
O7 | 0.8036 (4) | 0.9442 (6) | 0.6824 (4) | 0.0322 (10) | |
S1 | 0.12198 (11) | 0.75430 (17) | 0.53187 (10) | 0.0171 (3) | |
C1 | 0.5727 (5) | 0.6395 (7) | 0.6491 (4) | 0.0190 (11) | |
C2 | 0.4526 (4) | 0.5676 (7) | 0.6152 (4) | 0.0166 (11) | |
C3 | 0.4356 (5) | 0.3775 (7) | 0.6134 (4) | 0.0192 (11) | |
C4 | 0.3222 (5) | 0.3075 (7) | 0.5815 (4) | 0.0212 (11) | |
H4 | 0.3107 | 0.1825 | 0.5784 | 0.025* | |
C5 | 0.2282 (5) | 0.4219 (7) | 0.5549 (4) | 0.0207 (11) | |
H5A | 0.1529 | 0.3748 | 0.5346 | 0.025* | |
C6 | 0.2460 (4) | 0.6126 (7) | 0.5585 (4) | 0.0166 (10) | |
C7 | 0.3566 (4) | 0.6821 (7) | 0.5878 (4) | 0.0176 (11) | |
H7 | 0.3676 | 0.8072 | 0.5893 | 0.021* | |
H1 | 0.814 (6) | 0.959 (9) | 0.616 (3) | 0.05 (2)* | |
H2 | 0.767 (6) | 1.030 (7) | 0.705 (5) | 0.04 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Rb1 | 0.0330 (4) | 0.0361 (4) | 0.0383 (4) | −0.0030 (2) | 0.0098 (3) | 0.0022 (2) |
O1 | 0.025 (2) | 0.0163 (18) | 0.033 (2) | −0.0066 (15) | 0.0101 (17) | 0.0016 (14) |
O2 | 0.026 (2) | 0.034 (2) | 0.024 (2) | 0.0027 (18) | −0.0040 (16) | −0.0061 (17) |
O3 | 0.033 (2) | 0.029 (2) | 0.034 (2) | −0.0025 (17) | 0.0256 (18) | 0.0013 (17) |
O4 | 0.019 (2) | 0.035 (2) | 0.029 (2) | −0.0019 (17) | 0.0034 (16) | 0.0007 (17) |
O5 | 0.0201 (19) | 0.026 (2) | 0.028 (2) | −0.0101 (16) | 0.0060 (16) | −0.0034 (16) |
O6 | 0.029 (2) | 0.023 (2) | 0.028 (2) | 0.0059 (17) | 0.0044 (17) | 0.0050 (16) |
O7 | 0.039 (3) | 0.035 (2) | 0.027 (2) | −0.012 (2) | 0.0140 (19) | −0.0006 (18) |
S1 | 0.0165 (6) | 0.0188 (6) | 0.0174 (6) | −0.0031 (5) | 0.0065 (5) | −0.0011 (5) |
C1 | 0.021 (3) | 0.025 (3) | 0.012 (2) | −0.002 (2) | 0.006 (2) | −0.002 (2) |
C2 | 0.019 (3) | 0.021 (3) | 0.011 (2) | −0.005 (2) | 0.005 (2) | −0.0019 (18) |
C3 | 0.026 (3) | 0.021 (2) | 0.011 (2) | 0.001 (2) | 0.005 (2) | 0.0005 (19) |
C4 | 0.034 (3) | 0.015 (2) | 0.016 (3) | −0.006 (2) | 0.009 (2) | 0.0008 (19) |
C5 | 0.022 (3) | 0.023 (3) | 0.018 (3) | −0.008 (2) | 0.007 (2) | 0.000 (2) |
C6 | 0.020 (3) | 0.018 (2) | 0.013 (2) | 0.000 (2) | 0.005 (2) | −0.0018 (19) |
C7 | 0.020 (3) | 0.018 (2) | 0.016 (2) | −0.005 (2) | 0.007 (2) | −0.0025 (19) |
Geometric parameters (Å, º) top
Rb1—O4 | 2.847 (5) | O5—H5 | 0.8200 |
Rb1—O3i | 2.875 (4) | O6—C3 | 1.342 (7) |
Rb1—O2ii | 2.907 (4) | O6—H6 | 0.8200 |
Rb1—O3iii | 2.945 (5) | O7—Rb1ii | 3.466 (5) |
Rb1—O2 | 3.005 (4) | O7—H1 | 0.84 (6) |
Rb1—O7 | 3.014 (5) | O7—H2 | 0.85 (6) |
Rb1—O1iii | 3.110 (5) | S1—O2v | 1.451 (4) |
Rb1—O7iv | 3.466 (5) | S1—C6 | 1.763 (5) |
Rb1—S1iii | 3.601 (3) | S1—Rb1vii | 3.601 (3) |
Rb1—C5v | 3.633 (6) | S1—Rb1ix | 3.956 (3) |
Rb1—S1vi | 3.956 (3) | C1—C2 | 1.477 (7) |
Rb1—Rb1ii | 4.298 (3) | C2—C7 | 1.387 (7) |
O1—S1 | 1.466 (4) | C2—C3 | 1.413 (7) |
O1—Rb1vii | 3.110 (5) | C3—C4 | 1.400 (8) |
O2—S1v | 1.451 (4) | C4—C5 | 1.370 (8) |
O2—Rb1iv | 2.907 (4) | C4—H4 | 0.9300 |
O3—S1 | 1.465 (4) | C5—C6 | 1.419 (7) |
O3—Rb1viii | 2.875 (4) | C5—Rb1v | 3.633 (6) |
O3—Rb1vii | 2.945 (4) | C5—H5A | 0.9300 |
O4—C1 | 1.218 (7) | C6—C7 | 1.368 (7) |
O5—C1 | 1.320 (7) | C7—H7 | 0.9300 |
| | | |
O4—Rb1—O3i | 130.23 (13) | H1—O7—H2 | 114 (4) |
O4—Rb1—O2ii | 129.29 (12) | O2v—S1—O3 | 113.5 (3) |
O3i—Rb1—O2ii | 78.11 (13) | O2v—S1—O1 | 112.8 (2) |
O4—Rb1—O3iii | 93.24 (12) | O3—S1—O1 | 111.4 (2) |
O3i—Rb1—O3iii | 125.69 (9) | O2v—S1—C6 | 106.3 (2) |
O2ii—Rb1—O3iii | 99.84 (13) | O3—S1—C6 | 105.2 (2) |
O4—Rb1—O2 | 95.15 (11) | O1—S1—C6 | 107.0 (2) |
O3i—Rb1—O2 | 70.47 (13) | O4—C1—O5 | 122.5 (5) |
O2ii—Rb1—O2 | 135.55 (7) | O4—C1—C2 | 123.5 (5) |
O3iii—Rb1—O2 | 75.49 (13) | O5—C1—C2 | 114.1 (4) |
O4—Rb1—O7 | 71.01 (12) | C7—C2—C3 | 119.6 (5) |
O3i—Rb1—O7 | 77.69 (13) | C7—C2—C1 | 121.6 (4) |
O2ii—Rb1—O7 | 78.26 (12) | C3—C2—C1 | 118.8 (5) |
O3iii—Rb1—O7 | 156.01 (11) | O6—C3—C4 | 117.5 (5) |
O2—Rb1—O7 | 122.63 (12) | O6—C3—C2 | 123.0 (5) |
O4—Rb1—O1iii | 76.03 (11) | C4—C3—C2 | 119.5 (5) |
O3i—Rb1—O1iii | 152.69 (11) | C5—C4—C3 | 120.4 (5) |
O2ii—Rb1—O1iii | 78.05 (12) | C5—C4—H4 | 119.8 |
O3iii—Rb1—O1iii | 47.03 (10) | C3—C4—H4 | 119.8 |
O2—Rb1—O1iii | 120.19 (12) | C4—C5—C6 | 119.7 (5) |
O7—Rb1—O1iii | 110.06 (11) | C4—C5—Rb1v | 112.3 (3) |
O4—Rb1—O7iv | 159.61 (11) | C6—C5—Rb1v | 92.8 (3) |
O3i—Rb1—O7iv | 59.43 (12) | C4—C5—H5A | 120.2 |
O2ii—Rb1—O7iv | 66.97 (11) | C6—C5—H5A | 120.2 |
O3iii—Rb1—O7iv | 69.85 (11) | Rb1v—C5—H5A | 64.7 |
O2—Rb1—O7iv | 70.16 (10) | C7—C6—C5 | 120.2 (5) |
O7—Rb1—O7iv | 128.60 (11) | C6—C7—C2 | 120.6 (5) |
O1iii—Rb1—O7iv | 98.72 (11) | C6—C7—H7 | 119.7 |
C1—O5—H5 | 109.5 | C2—C7—H7 | 119.7 |
C3—O6—H6 | 109.5 | | |
| | | |
O4—C1—C2—C3 | −5.4 (7) | | |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+2, y−1/2, −z+3/2; (v) −x+1, −y+1, −z+1; (vi) x+1, −y+3/2, z+1/2; (vii) −x+1, y+1/2, −z+3/2; (viii) x−1, y, z; (ix) x−1, −y+3/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O7 | 0.82 | 1.92 | 2.729 (6) | 171 |
O6—H6···O4 | 0.82 | 1.89 | 2.613 (6) | 146 |
O7—H1···O1x | 0.84 (4) | 1.97 (4) | 2.797 (8) | 166 (1) |
Symmetry code: (x) −x+1, −y+2, −z+1. |