Bis­(guanidinium) 5-sulfosalicyl­ate monohydrate

The crystal structure of the hydrated proton-transfer compound hydrate of 3-carboxy-4-hydroxy­benzene­sulfonic acid (5-sulfosalicylic acid) with guanidine, 2CH₆N₃⁺·C₇H₄O₆S^2-·H₂O, reveals the presence of an extensively hydrogen-bonded three-dimensional network polymer in which all proton donor and acceptor atoms on the two guanidine cations, the dianionic sulfosalicyl­ate anion and the water mol­ecule are utilized. The structure is significantly different chemically and structurally from that of the previously reported an­hydro­us guanidinium sulfosalicyl­ate compound CH₆N₃⁺·C₇H₅O₆S^-.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.140
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C12
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.49
           From the CIF: _reflns_number_total               2173
           Count of symmetry unique reflns         2094
           Completeness (_total/calc)            103.77%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        79
           Fraction of Friedel pairs measured     0.038
           Are heavy atom types Z>Si present          yes

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

(I)

Crystal data

2CH6N3^+·C7H4O6S^2^−·H2O	Dx = 1.490 Mg m^−3
Mr = 354.35	Melting point = 478.5–484.1 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 12.030 (3) Å	θ = 12.5–17.4°
b = 18.010 (5) Å	µ = 0.25 mm^−1
c = 7.290 (2) Å	T = 295 K
V = 1579.5 (7) Å^3	Prism, colourless
Z = 4	0.45 × 0.35 × 0.30 mm
F(000) = 744

Data collection

Rigaku AFC-7R diffractometer	1644 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.028
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
ω–2θ scans	h = −6→15
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999)	k = 0→23
Tmin = 0.895, Tmax = 0.928	l = −3→9
2428 measured reflections	3 standard reflections every 150 reflections
2173 independent reflections	intensity decay: 0.3%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 2.556P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max = 0.015
S = 0.90	Δρmax = 0.44 e Å^−3
2173 reflections	Δρmin = −0.45 e Å^−3
261 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.059 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 79 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.1 (2)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
S5	0.31812 (7)	0.21494 (5)	0.5031 (2)	0.0359 (3)
O2	0.2675 (2)	−0.11002 (13)	0.5046 (7)	0.0456 (9)
O51	0.4352 (2)	0.23381 (15)	0.5074 (7)	0.0484 (9)
O52	0.2646 (3)	0.2396 (2)	0.3331 (5)	0.0487 (12)
O53	0.2590 (3)	0.2426 (2)	0.6645 (5)	0.0467 (12)
O71	−0.0090 (2)	0.02380 (17)	0.5051 (8)	0.0641 (12)
O72	0.0603 (2)	−0.09012 (15)	0.5092 (8)	0.0548 (9)
C1	0.1857 (3)	0.01113 (18)	0.5073 (8)	0.0320 (9)
C2	0.2797 (3)	−0.03504 (18)	0.5055 (9)	0.0343 (9)
C3	0.3852 (3)	−0.0046 (2)	0.5030 (11)	0.0426 (10)
C4	0.3993 (3)	0.0716 (2)	0.5026 (9)	0.0390 (10)
C5	0.3066 (3)	0.11746 (18)	0.5068 (7)	0.0326 (9)
C6	0.2013 (3)	0.08740 (18)	0.5108 (8)	0.0325 (9)
C7	0.0706 (3)	−0.0196 (2)	0.5083 (11)	0.0432 (11)
N12	0.6373 (4)	0.1236 (3)	0.7752 (8)	0.0573 (19)
N22	0.8109 (4)	0.0943 (3)	0.6753 (8)	0.0620 (16)
N32	0.6961 (5)	0.0027 (3)	0.7800 (10)	0.080 (2)
C12	0.7150 (4)	0.0736 (3)	0.7432 (7)	0.0507 (14)
N11	0.0412 (5)	0.2039 (3)	0.8465 (8)	0.0513 (17)
N21	0.0364 (4)	0.1951 (3)	1.1595 (8)	0.0550 (19)
N31	−0.1173 (3)	0.23667 (19)	1.0044 (8)	0.0455 (10)
C11	−0.0130 (3)	0.21230 (19)	1.0045 (9)	0.0378 (10)
O1W	0.8614 (5)	−0.1118 (3)	0.7534 (9)	0.0727 (18)
H2	0.188 (5)	−0.117 (3)	0.526 (9)	0.066 (16)*
H3	0.448400	−0.036300	0.501600	0.0510*
H4	0.471700	0.092400	0.498000	0.0470*
H6	0.138300	0.119300	0.519000	0.0390*
H12A	0.578 (3)	0.114 (3)	0.846 (6)	0.065 (10)*
H12B	0.655 (4)	0.169 (3)	0.739 (7)	0.061 (14)*
H22A	0.864 (6)	0.062 (4)	0.639 (9)	0.09 (2)*
H22B	0.837 (7)	0.147 (5)	0.677 (12)	0.10 (3)*
H32A	0.750 (7)	−0.035 (5)	0.771 (11)	0.11 (3)*
H32B	0.635 (6)	−0.009 (4)	0.817 (12)	0.09 (2)*
H11A	0.106 (6)	0.215 (4)	0.838 (9)	0.08 (2)*
H11B	0.010 (4)	0.222 (3)	0.744 (7)	0.061 (15)*
H21A	0.103 (4)	0.184 (3)	1.160 (7)	0.065 (14)*
H21B	0.006 (5)	0.198 (3)	1.270 (8)	0.060 (16)*
H1A	0.921 (9)	−0.105 (6)	0.681 (10)	0.10 (3)*
H1B	0.825 (10)	−0.156 (6)	0.778 (10)	0.11 (3)*
H31A	−0.164 (5)	0.246 (5)	1.114 (9)	0.08 (3)*
H31B	−0.157 (5)	0.245 (5)	0.892 (9)	0.09 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S5	0.0386 (5)	0.0307 (4)	0.0385 (5)	−0.0045 (3)	0.0000 (8)	−0.0005 (7)
O2	0.0437 (14)	0.0272 (12)	0.0660 (18)	0.0035 (10)	0.004 (3)	0.004 (2)
O51	0.0460 (15)	0.0437 (14)	0.0554 (17)	−0.0127 (11)	−0.001 (2)	−0.002 (3)
O52	0.061 (2)	0.037 (2)	0.048 (2)	0.0053 (19)	−0.0051 (19)	0.0085 (16)
O53	0.055 (2)	0.041 (2)	0.044 (2)	−0.0067 (19)	0.0050 (18)	−0.0082 (16)
O71	0.0271 (12)	0.0512 (16)	0.114 (3)	0.0016 (11)	0.000 (3)	−0.015 (3)
O72	0.0399 (14)	0.0365 (13)	0.088 (2)	−0.0082 (11)	0.001 (3)	−0.002 (3)
C1	0.0302 (15)	0.0317 (15)	0.0340 (17)	−0.0007 (12)	0.000 (3)	−0.004 (2)
C2	0.0369 (16)	0.0302 (15)	0.0357 (18)	0.0018 (13)	0.006 (3)	0.003 (3)
C3	0.0307 (15)	0.0410 (18)	0.056 (2)	0.0075 (14)	0.002 (4)	0.003 (4)
C4	0.0281 (15)	0.0410 (18)	0.048 (2)	−0.0022 (13)	−0.003 (3)	−0.005 (4)
C5	0.0357 (16)	0.0317 (15)	0.0303 (16)	−0.0026 (12)	−0.002 (3)	0.001 (2)
C6	0.0323 (15)	0.0300 (15)	0.0352 (18)	0.0021 (12)	−0.001 (3)	−0.002 (2)
C7	0.0359 (17)	0.0407 (18)	0.053 (2)	−0.0032 (14)	0.002 (3)	−0.002 (4)
N12	0.040 (3)	0.046 (3)	0.086 (4)	0.002 (2)	0.017 (3)	0.013 (3)
N22	0.051 (2)	0.045 (2)	0.090 (4)	0.003 (2)	0.020 (3)	0.000 (2)
N32	0.059 (3)	0.047 (2)	0.134 (5)	0.007 (2)	0.021 (4)	0.027 (3)
C12	0.046 (2)	0.043 (2)	0.063 (3)	0.000 (2)	0.004 (2)	0.007 (2)
N11	0.047 (3)	0.058 (3)	0.049 (3)	0.005 (3)	0.005 (3)	−0.002 (3)
N21	0.046 (3)	0.073 (4)	0.046 (3)	0.017 (3)	−0.004 (3)	−0.009 (3)
N31	0.0389 (16)	0.0494 (17)	0.0483 (18)	0.0098 (14)	−0.003 (3)	0.002 (3)
C11	0.0374 (17)	0.0315 (16)	0.0444 (19)	−0.0001 (13)	−0.001 (3)	−0.006 (3)
O1W	0.062 (3)	0.050 (2)	0.106 (4)	0.003 (2)	0.007 (3)	0.006 (3)

Geometric parameters (Å, º)

S5—O51	1.449 (3)	N12—C12	1.319 (7)
S5—O52	1.465 (4)	N22—C12	1.310 (7)
S5—O53	1.462 (4)	N32—C12	1.324 (8)
S5—C5	1.761 (3)	N12—H12B	0.89 (5)
O2—C2	1.358 (4)	N12—H12A	0.90 (4)
O71—C7	1.236 (5)	N22—H22A	0.90 (7)
O72—C7	1.276 (5)	N22—H22B	1.00 (9)
O2—H2	0.98 (6)	N32—H32B	0.81 (7)
O1W—H1B	0.93 (11)	N32—H32A	0.94 (9)
O1W—H1A	0.90 (10)	C1—C6	1.387 (5)
N11—C11	1.332 (8)	C1—C7	1.491 (5)
N21—C11	1.314 (8)	C1—C2	1.404 (5)
N31—C11	1.329 (5)	C2—C3	1.383 (5)
N11—H11B	0.90 (5)	C3—C4	1.383 (5)
N11—H11A	0.81 (7)	C4—C5	1.388 (5)
N21—H21A	0.83 (5)	C5—C6	1.378 (5)
N21—H21B	0.89 (6)	C3—H3	0.9508
N31—H31A	0.99 (7)	C4—H4	0.9487
N31—H31B	0.96 (7)	C6—H6	0.9529
O51—S5—O52	112.0 (2)	C2—C1—C6	118.6 (3)
O51—S5—O53	112.0 (2)	C2—C1—C7	121.9 (3)
O51—S5—C5	108.05 (17)	C1—C2—C3	120.3 (3)
O52—S5—O53	111.3 (2)	O2—C2—C3	119.6 (3)
O52—S5—C5	106.3 (2)	O2—C2—C1	120.1 (3)
O53—S5—C5	106.8 (2)	C2—C3—C4	120.4 (3)
C2—O2—H2	103 (3)	C3—C4—C5	119.5 (3)
H1A—O1W—H1B	127 (9)	S5—C5—C4	122.0 (3)
H11A—N11—H11B	104 (6)	S5—C5—C6	117.7 (3)
C11—N11—H11A	121 (5)	C4—C5—C6	120.3 (3)
C11—N11—H11B	118 (3)	C1—C6—C5	120.9 (3)
H21A—N21—H21B	114 (5)	O72—C7—C1	117.4 (3)
C11—N21—H21A	120 (4)	O71—C7—O72	123.7 (3)
C11—N21—H21B	126 (4)	O71—C7—C1	119.0 (3)
H31A—N31—H31B	112 (5)	C4—C3—H3	119.85
C11—N31—H31B	121 (4)	C2—C3—H3	119.74
C11—N31—H31A	126 (4)	C3—C4—H4	120.30
C12—N12—H12B	114 (3)	C5—C4—H4	120.23
H12A—N12—H12B	123 (5)	C5—C6—H6	119.71
C12—N12—H12A	122 (3)	C1—C6—H6	119.39
C12—N22—H22B	123 (5)	N11—C11—N21	119.7 (4)
H22A—N22—H22B	113 (7)	N11—C11—N31	119.9 (6)
C12—N22—H22A	123 (5)	N21—C11—N31	120.4 (6)
H32A—N32—H32B	117 (7)	N12—C12—N22	119.8 (5)
C12—N32—H32B	118 (5)	N12—C12—N32	120.1 (5)
C12—N32—H32A	124 (5)	N22—C12—N32	120.1 (5)
C6—C1—C7	119.6 (3)
O51—S5—C5—C4	−3.6 (6)	C6—C1—C2—C3	−1.5 (9)
O51—S5—C5—C6	177.5 (4)	C7—C1—C2—O2	0.0 (9)
O52—S5—C5—C4	116.7 (5)	C7—C1—C2—C3	179.4 (7)
O52—S5—C5—C6	−62.1 (5)	C2—C1—C7—O71	−178.2 (7)
O53—S5—C5—C4	−124.3 (5)	O2—C2—C3—C4	179.6 (7)
O53—S5—C5—C6	56.8 (5)	C1—C2—C3—C4	0.1 (11)
C6—C1—C7—O72	−178.4 (6)	C2—C3—C4—C5	0.7 (11)
C6—C1—C7—O71	2.8 (10)	C3—C4—C5—S5	−179.0 (5)
C2—C1—C6—C5	2.0 (9)	C3—C4—C5—C6	−0.2 (9)
C7—C1—C6—C5	−178.9 (6)	C4—C5—C6—C1	−1.2 (9)
C2—C1—C7—O72	0.6 (10)	S5—C5—C6—C1	177.7 (5)
C6—C1—C2—O2	179.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O72	0.98 (6)	1.62 (6)	2.518 (3)	152 (5)
O1W—H1A···O72^i	0.90 (10)	2.11 (10)	3.008 (7)	179 (9)
O1W—H1B···O53^ii	0.93 (11)	2.13 (11)	3.055 (7)	180 (8)
N11—H11A···O53	0.81 (7)	2.29 (7)	3.018 (7)	151 (6)
N11—H11B···O51^iii	0.90 (5)	2.19 (5)	3.089 (7)	180 (5)
N12—H12A···O72^iv	0.90 (4)	2.09 (4)	2.987 (7)	179 (5)
N12—H12B···O52^v	0.89 (5)	2.17 (5)	3.006 (6)	157 (4)
N21—H21A···O52^vi	0.83 (5)	2.52 (5)	3.127 (6)	131 (5)
N21—H21A···O2^iv	0.83 (5)	2.34 (5)	3.031 (6)	141 (5)
N21—H21B···O51^vii	0.89 (6)	2.21 (6)	3.003 (7)	149 (5)
N22—H22A···O71^i	0.90 (7)	1.94 (7)	2.801 (6)	159 (6)
N22—H22B···O52^v	1.00 (9)	2.22 (9)	3.043 (7)	139 (7)
N31—H31A···O53^vii	0.99 (7)	1.87 (6)	2.860 (6)	174 (6)
N31—H31B···O52^iii	0.96 (7)	1.91 (7)	2.873 (7)	179 (8)
N32—H32A···O1W	0.94 (9)	1.93 (9)	2.871 (8)	180 (8)
N32—H32B···O71^iv	0.81 (7)	2.06 (8)	2.826 (8)	157 (8)
C4—H4···O51	0.95	2.59	2.953 (5)	103

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1/2, −y, z+1/2; (v) x+1/2, −y+1/2, −z+1; (vi) x, y, z+1; (vii) x−1/2, −y+1/2, −z+2.