Hydro­gen trisodium bis(5-sulfonatosalicyl­ate) monohydrate

The crystal structure of the title compound, 3Na⁺·H⁺·2C₇H₄O₆S^2-·H₂O, features a trianion in which two 5-sulfonatosalicyl­ate units are linked by an acid H atom through the negatively charged carboxyl O atoms. The trianion lies on a center of inversion, as does one of the sodium ions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.089
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       7.14 Ratio

Author Response: The temperature factor of the acid hydrogen is refined.

PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O4     -   H4O    ...       1.24 Ang.

Author Response: The bond is an "acid hydrogen" bond. The bond is discussed.

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O2
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
              O1W  -H1W     1.555   1.555

Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       9.40
            Cell volume su given      =       6.00
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Na2
PLAT731_ALERT_1_C Bond    Calc    2.561(3), Rep  2.5610(10) ......       3.00 su-Rat
              NA1  -O6      1.555   4.555
PLAT731_ALERT_1_C Bond    Calc    2.561(3), Rep  2.5610(10) ......       3.00 su-Rat
              NA1  -O6      1.555   6.585
PLAT736_ALERT_1_C H...A   Calc     2.29(5), Rep     2.29(2) ......       2.50 su-Rat
              H1W  -O3      1.555   2.665

   2 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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.

Trisodium [hydrogen bis(5-sulfonatosalicylate)] monohydrate

Crystal data

3Na^+·H^+·2C7H4O6S^2^−·H2O	F(000) = 1056
Mr = 520.32	Dx = 1.936 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7762 reflections
a = 22.563 (5) Å	θ = 3.6–27.5°
b = 5.464 (1) Å	µ = 0.45 mm^−1
c = 17.901 (4) Å	T = 295 K
β = 126.02 (3)°	Block, colorless
V = 1785.1 (6) Å^3	0.38 × 0.29 × 0.22 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2034 independent reflections
Radiation source: fine-focus sealed tube	1889 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −28→28
Tmin = 0.788, Tmax = 0.908	k = −7→7
8215 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0556P)^2 + 2.0813P] where P = (Fo^2 + 2Fc^2)/3
2034 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.45 e Å^−3
2 restraints	Δρmin = −0.37 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.34683 (2)	1.28216 (7)	0.16723 (2)	0.0184 (1)
Na1	0.2500	1.7500	0.0000	0.0271 (2)
Na2	0.47891 (4)	1.5441 (1)	0.14459 (4)	0.0279 (2)
O1	0.2885 (1)	1.4476 (3)	0.1070 (1)	0.0482 (4)
O2	0.4190 (1)	1.3826 (4)	0.2052 (1)	0.0569 (5)
O3	0.3383 (1)	1.0432 (2)	0.1279 (1)	0.0394 (3)
O4	0.4692 (1)	0.6732 (2)	0.4456 (1)	0.0215 (2)
O5	0.4352 (1)	0.7698 (2)	0.5362 (1)	0.0259 (3)
O6	0.3661 (1)	1.1819 (2)	0.5084 (1)	0.0239 (3)
O1w	0.5000	1.8655 (4)	0.2500	0.0406 (5)
C1	0.3462 (1)	1.2395 (3)	0.2645 (1)	0.0163 (3)
C2	0.3835 (1)	1.0410 (3)	0.3216 (1)	0.0178 (3)
C3	0.3907 (1)	1.0136 (3)	0.4039 (1)	0.0166 (3)
C4	0.3588 (1)	1.1896 (3)	0.4273 (1)	0.0173 (3)
C5	0.3192 (1)	1.3839 (3)	0.3680 (1)	0.0198 (3)
C6	0.3136 (1)	1.4107 (3)	0.2872 (1)	0.0187 (3)
C7	0.4340 (1)	0.8060 (3)	0.4668 (1)	0.0186 (3)
H4o	0.5000	0.5000	0.5000	0.09 (1)*
H6o	0.384 (1)	1.045 (3)	0.533 (2)	0.049 (7)*
H1w	0.540 (2)	1.946 (8)	0.278 (3)	0.15 (2)*
H2	0.4040	0.9252	0.3048	0.021*
H5	0.2965	1.4959	0.3827	0.024*
H6	0.2880	1.5425	0.2483	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0210 (2)	0.0203 (2)	0.0137 (2)	0.0002 (1)	0.0101 (2)	0.0036 (1)
Na1	0.0300 (5)	0.0282 (5)	0.0247 (5)	0.0069 (4)	0.0170 (4)	0.0109 (4)
Na2	0.0364 (4)	0.0286 (4)	0.0219 (3)	−0.0075 (3)	0.0189 (3)	−0.0062 (3)
O1	0.068 (1)	0.051 (1)	0.033 (1)	0.036 (1)	0.034 (1)	0.028 (1)
O2	0.040 (1)	0.106 (2)	0.027 (1)	−0.039 (1)	0.022 (1)	−0.009 (1)
O3	0.071 (1)	0.026 (1)	0.034 (1)	−0.001 (1)	0.038 (1)	−0.003 (1)
O4	0.023 (1)	0.021 (1)	0.020 (1)	0.007 (1)	0.013 (1)	0.007 (1)
O5	0.034 (1)	0.026 (1)	0.020 (1)	0.008 (1)	0.017 (1)	0.009 (1)
O6	0.032 (1)	0.025 (1)	0.020 (1)	0.003 (1)	0.018 (1)	0.003 (1)
O1w	0.065 (2)	0.024 (1)	0.048 (1)	0.000	0.042 (1)	0.000
C1	0.017 (1)	0.018 (1)	0.014 (1)	−0.001 (1)	0.008 (1)	0.003 (1)
C2	0.019 (1)	0.018 (1)	0.018 (1)	0.003 (1)	0.011 (1)	0.003 (1)
C3	0.017 (1)	0.017 (1)	0.015 (1)	0.000 (1)	0.008 (1)	0.003 (1)
C4	0.018 (1)	0.020 (1)	0.015 (1)	−0.003 (1)	0.010 (1)	−0.001 (1)
C5	0.019 (1)	0.019 (1)	0.021 (1)	0.002 (1)	0.012 (1)	0.000 (1)
C6	0.019 (1)	0.016 (1)	0.018 (1)	0.003 (1)	0.009 (1)	0.004 (1)
C7	0.019 (1)	0.018 (1)	0.016 (1)	−0.001 (1)	0.008 (1)	0.003 (1)

Geometric parameters (Å, º)

S1—O1	1.430 (1)	O4—C7	1.286 (2)
S1—O2	1.453 (1)	O5—C7	1.243 (2)
S1—O3	1.442 (1)	O6—C4	1.362 (2)
S1—C1	1.764 (2)	C1—C2	1.385 (2)
Na1—O1	2.280 (1)	C1—C6	1.392 (2)
Na1—O1^i	2.280 (1)	C2—C3	1.393 (2)
Na1—O3^ii	2.533 (2)	C3—C4	1.405 (2)
Na1—O3^iii	2.533 (2)	C3—C7	1.489 (2)
Na1—O6^iv	2.561 (1)	C4—C5	1.392 (2)
Na1—O6^v	2.561 (1)	C5—C6	1.382 (2)
Na2—O2	2.347 (2)	O4—H4o	1.238
Na2—O2^vi	2.456 (2)	O6—H6o	0.85 (1)
Na2—O4^vii	2.589 (1)	O1w—H1w	0.85 (1)
Na2—O5^viii	2.330 (1)	C2—H2	0.93
Na2—O6^v	2.715 (2)	C5—H5	0.93
Na2—O1w	2.412 (2)	C6—H6	0.93
O1—S1—O2	113.3 (1)	S1—O2—Na2^vi	136.0 (1)
O1—S1—O3	113.9 (1)	Na2—O2—Na2^vi	86.9 (1)
O1—S1—C1	106.8 (1)	S1—O3—Na1^ix	145.4 (1)
O2—S1—O3	111.2 (1)	C7—O4—Na2^x	157.2 (1)
O2—S1—C1	104.2 (1)	C7—O5—Na2^xi	134.4 (1)
O3—S1—C1	106.6 (1)	C4—O6—Na1^xii	117.0 (1)
O1—Na1—O1^i	180	C4—O6—Na2^xiii	113.7 (1)
O1—Na1—O3^ii	89.5 (1)	Na1^xii—O6—Na2^xiii	111.0 (1)
O1—Na1—O3^iii	90.5 (1)	Na2—O1w—Na2^vi	86.5 (1)
O1—Na1—O6^iv	79.3 (1)	C2—C1—S1	118.5 (1)
O1—Na1—O6^v	100.7 (1)	C6—C1—S1	120.8 (1)
O1^i—Na1—O3^ii	90.5 (1)	C2—C1—C6	120.5 (1)
O1^i—Na1—O3^iii	89.5 (1)	C1—C2—C3	120.4 (1)
O1^i—Na1—O6^iv	100.7 (1)	C2—C3—C4	118.8 (1)
O1^i—Na1—O6^v	79.3 (1)	C2—C3—C7	119.9 (1)
O3^ii—Na1—O3^iii	180	C4—C3—C7	121.3 (1)
O3^ii—Na1—O6^v	67.8 (1)	O6—C4—C5	117.3 (1)
O3^ii—Na1—O6^iv	112.2 (1)	O6—C4—C3	122.3 (1)
O3^iii—Na1—O6^iv	67.8 (1)	C3—C4—C5	120.4 (1)
O3^iii—Na1—O6^v	112.2 (1)	C4—C5—C5	120.2 (1)
O6^iv—Na1—O6^v	180	C1—C6—C5	119.7 (1)
O2—Na2—O2^vi	77.5 (1)	O5—C7—O4	123.4 (1)
O2—Na2—O4^vii	170.3 (1)	O5—C7—C3	119.7 (1)
O2—Na2—O5^viii	91.8 (1)	O4—C7—C3	116.9 (1)
O2—Na2—O6^v	97.6 (1)	C7—O4—H4o	111.0
O2—Na2—O1w	79.3 (1)	Na2^x—O4—H4o	91.8 (1)
O2^vi—Na2—O4^vii	107.7 (1)	C4—O6—H6o	107 (2)
O2^vi—Na2—O5^viii	108.2 (1)	Na1^xii—O6—H6o	109 (2)
O2^vi—Na2—O6^v	164.2 (1)	Na2^xiii—O6—H6o	96 (2)
O2^vi—Na2—O1w	77.2 (1)	Na2—O1w—H1w	120 (3)
O4^vii—Na2—O5^viii	78.9 (1)	Na2^vi—O1w—H1w	105 (3)
O4^vii—Na2—O6^v	79.6 (1)	C1—C2—H2	119.8
O4^vii—Na2—O1w	109.6 (1)	C3—C2—H2	119.8
O5^viii—Na2—O6^v	86.8 (1)	C6—C5—H5	119.9
O5^viii—Na2—O1w	168.5 (1)	C4—C5—H5	119.9
O6^v—Na2—O1w	87.2 (1)	C5—C6—H6	120.1
S1—O1—Na1	144.9 (1)	C1—C6—H6	120.1
S1—O2—Na2	135.8 (1)
O3—S1—O1—Na1	−94.3 (2)	O3—S1—C1—C2	40.8 (1)
O2—S1—O1—Na1	34.2 (2)	O2—S1—C1—C2	−76.8 (2)
C1—S1—O1—Na1	148.3 (2)	O1—S1—C1—C6	−21.6 (2)
O3^ii—Na1—O1—S1	−73.8 (2)	O3—S1—C1—C6	−143.7 (1)
O3^iii—Na1—O1—S1	106.2 (2)	O2—S1—C1—C6	98.6 (2)
O6^v—Na1—O1—S1	−6.6 (2)	C6—C1—C2—C3	−1.8 (2)
O6^iv—Na1—O1—S1	173.4 (2)	S1—C1—C2—C3	173.6 (1)
O1—S1—O2—Na2	−57.4 (2)	C1—C2—C3—C4	0.6 (2)
O3—S1—O2—Na2	72.4 (2)	C1—C2—C3—C7	−177.0 (1)
C1—S1—O2—Na2	−173.1 (2)	Na1^xii—O6—C4—C5	47.1 (2)
O1—S1—O2—Na2^vi	105.3 (2)	Na2^xiii—O6—C4—C5	−84.5 (1)
O3—S1—O2—Na2^vi	−124.8 (2)	Na1^xii—O6—C4—C3	−134.2 (1)
C1—S1—O2—Na2^vi	−10.4 (2)	Na2^xiii—O6—C4—C3	94.2 (1)
O5^viii—Na2—O2—S1	−44.2 (2)	C2—C3—C4—O6	−177.0 (1)
O1w—Na2—O2—S1	128.4 (2)	C7—C3—C4—O6	0.6 (2)
O2^vi—Na2—O2—S1	−152.5 (2)	C2—C3—C4—C5	1.7 (2)
O6^v—Na2—O2—S1	42.7 (2)	C7—C3—C4—C5	179.2 (1)
O5^viii—Na2—O2—Na2^vi	147.7 (1)	O6—C4—C5—C6	176.0 (1)
O1w—Na2—O2—Na2^vi	−39.7 (1)	C3—C4—C5—C6	−2.7 (2)
O2^vi—Na2—O2—Na2^vi	39.4 (1)	C4—C5—C6—C1	1.4 (2)
O6^v—Na2—O2—Na2^vi	−125.4 (1)	C2—C1—C6—C5	0.8 (2)
O1—S1—O3—Na1^ix	−15.3 (2)	S1—C1—C6—C5	−174.5 (1)
O2—S1—O3—Na1^ix	−144.9 (1)	Na2^xi—O5—C7—O4	−10.0 (2)
C1—S1—O3—Na1^ix	102.2 (1)	Na2^xi—O5—C7—C3	170.5 (1)
O5^viii—Na2—O1w—Na2^vi	80.5 (3)	Na2^x—O4—C7—O5	−172.4 (2)
O2—Na2—O1w—Na2^vi	40.6 (1)	Na2^x—O4—C7—C3	7.2 (3)
O2^vi—Na2—O1w—Na2^vi	−38.8 (1)	C2—C3—C7—O5	−173.9 (1)
O4^vii—Na2—O1w—Na2^vi	−143.3 (1)	C4—C3—C7—O5	8.6 (2)
O6^v—Na2—O1w—Na2^vi	138.9 (1)	C2—C3—C7—O4	6.5 (2)
O1—S1—C1—C2	163.0 (1)	C4—C3—C7—O4	−171.0 (1)

Symmetry codes: (i) −x+1/2, −y+7/2, −z; (ii) x, y+1, z; (iii) −x+1/2, −y+5/2, −z; (iv) −x+1/2, y+1/2, −z+1/2; (v) x, −y+3, z−1/2; (vi) −x+1, y, −z+1/2; (vii) −x+1, y+1, −z+1/2; (viii) x, −y+2, z−1/2; (ix) x, y−1, z; (x) −x+1, y−1, −z+1/2; (xi) x, −y+2, z+1/2; (xii) −x+1/2, y−1/2, −z+1/2; (xiii) x, −y+3, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O4^xiv	1.24	1.24	2.475 (2)	180
O6—H6o···O5	0.85 (1)	1.87 (2)	2.615 (2)	147 (2)
O1w—H1w···O2^vii	0.85 (1)	2.51 (3)	3.200 (3)	139 (4)
O1w—H1w···O3^vii	0.85 (1)	2.29 (2)	3.107 (2)	162 (5)

Symmetry codes: (vii) −x+1, y+1, −z+1/2; (xiv) −x+1, −y+1, −z+1.