Guanidinium 4-hydroxy-3-carboxy­benzenesulfonate

The anions of guanidinium 4-hydroxy-3-carboxy­benzene­sulfonate, CH₆N₃⁺·C₇H₅O₆S⁻, are linked into a linear chain by a short O_carboxyl...O_sulfonate interaction of 2.611 (2) Å; the hydroxyl group is linked intramolecularly to the carbonyl O atom, also by a short hydrogen bond [O...O = 2.601 (2) Å]. Adjacent chains are connected into a three-dimensional network structure through hydrogen-bonding interactions with the cation.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.112
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

Guanidinium 4-hydroxy-3-carboxybenzene sulfonate

Crystal data

CH6N3^+·C7H5O6S^−	Z = 2
Mr = 277.26	F(000) = 288
Triclinic, P1	Dx = 1.583 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4072 (6) Å	Cell parameters from 2298 reflections
b = 8.6995 (7) Å	θ = 2.5–28.0°
c = 10.2525 (8) Å	µ = 0.30 mm^−1
α = 87.205 (1)°	T = 298 K
β = 74.517 (1)°	Plate, colorless
γ = 66.277 (1)°	0.31 × 0.13 × 0.05 mm
V = 581.60 (8) Å^3

Data collection

Bruker SMART APEX area-detector diffractometer	2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
ω and φ scan	h = −8→9
5004 measured reflections	k = −11→11
2564 independent reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.0934P] where P = (Fo^2 + 2Fc^2)/3
2564 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.22 e Å^−3
11 restraints	Δρmin = −0.33 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.83760 (6)	0.84248 (5)	0.70760 (4)	0.0364 (2)
O1	0.6389 (2)	0.9598 (2)	0.6971 (1)	0.0492 (3)
O2	0.9506 (2)	0.7199 (2)	0.5919 (1)	0.0463 (3)
O3	0.9595 (2)	0.9274 (2)	0.7357 (1)	0.0461 (3)
O4	0.8556 (2)	0.2435 (2)	0.8019 (1)	0.0560 (4)
O5	0.7601 (2)	0.2181 (2)	1.0246 (1)	0.0519 (3)
O6	0.6677 (2)	0.4730 (2)	1.1892 (1)	0.0519 (4)
N1	0.3895 (3)	0.8336 (2)	0.6066 (2)	0.0562 (4)
N2	0.6772 (3)	0.6794 (2)	0.4409 (2)	0.0527 (4)
N3	0.3682 (3)	0.6795 (2)	0.4418 (2)	0.0486 (4)
C1	0.7936 (2)	0.7276 (2)	0.8501 (2)	0.0335 (3)
C2	0.8123 (2)	0.5654 (2)	0.8335 (2)	0.0350 (3)
C3	0.7713 (2)	0.4761 (2)	0.9455 (2)	0.0349 (4)
C4	0.7091 (3)	0.5536 (2)	1.0758 (2)	0.0379 (4)
C5	0.6892 (3)	0.7183 (2)	1.0916 (2)	0.0431 (4)
C6	0.7316 (3)	0.8043 (2)	0.9803 (2)	0.0395 (4)
C7	0.7943 (3)	0.3002 (2)	0.9296 (2)	0.0393 (4)
C8	0.4772 (3)	0.7315 (2)	0.4966 (2)	0.0416 (4)
H4o	0.879 (4)	0.142 (2)	0.788 (3)	0.087 (9)*
H6o	0.694 (4)	0.375 (2)	1.158 (3)	0.084 (9)*
H1n1	0.263 (2)	0.871 (3)	0.643 (2)	0.059 (6)*
H1n2	0.459 (3)	0.873 (3)	0.636 (2)	0.054 (6)*
H2n1	0.751 (3)	0.708 (3)	0.477 (2)	0.060 (7)*
H2n2	0.734 (3)	0.602 (2)	0.377 (2)	0.072 (7)*
H3n1	0.425 (3)	0.621 (2)	0.366 (1)	0.059 (6)*
H3n2	0.238 (2)	0.716 (3)	0.478 (2)	0.064 (7)*
H2	0.851 (3)	0.512 (2)	0.747 (1)	0.043 (5)*
H5	0.649 (3)	0.771 (3)	1.180 (1)	0.066 (6)*
H6	0.718 (3)	0.917 (1)	0.993 (2)	0.047 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0411 (3)	0.0286 (2)	0.0400 (2)	−0.0164 (2)	−0.0074 (2)	−0.0028 (2)
O1	0.051 (1)	0.039 (1)	0.057 (1)	−0.015 (1)	−0.019 (1)	0.005 (1)
O2	0.056 (1)	0.041 (1)	0.042 (1)	−0.025 (1)	−0.002 (1)	−0.008 (1)
O3	0.049 (1)	0.037 (1)	0.056 (1)	−0.025 (1)	−0.006 (1)	−0.007 (1)
O4	0.087 (1)	0.033 (1)	0.051 (1)	−0.031 (1)	−0.011 (1)	−0.006 (1)
O5	0.066 (1)	0.039 (1)	0.055 (1)	−0.027 (1)	−0.014 (1)	0.007 (1)
O6	0.067 (1)	0.044 (1)	0.041 (1)	−0.023 (1)	−0.006 (1)	0.002 (1)
N1	0.044 (1)	0.067 (1)	0.055 (1)	−0.022 (1)	−0.007 (1)	−0.014 (1)
N2	0.045 (1)	0.063 (1)	0.050 (1)	−0.024 (1)	−0.007 (1)	−0.009 (1)
N3	0.049 (1)	0.053 (1)	0.048 (1)	−0.025 (1)	−0.013 (1)	0.002 (1)
C1	0.032 (1)	0.028 (1)	0.040 (1)	−0.012 (1)	−0.009 (1)	−0.002 (1)
C2	0.037 (1)	0.030 (1)	0.038 (1)	−0.014 (1)	−0.008 (1)	−0.006 (1)
C3	0.033 (1)	0.029 (1)	0.042 (1)	−0.012 (1)	−0.009 (1)	−0.004 (1)
C4	0.036 (1)	0.035 (1)	0.040 (1)	−0.012 (1)	−0.008 (1)	0.000 (1)
C5	0.049 (1)	0.036 (1)	0.039 (1)	−0.013 (1)	−0.010 (1)	−0.009 (1)
C6	0.045 (1)	0.028 (1)	0.044 (1)	−0.013 (1)	−0.011 (1)	−0.007 (1)
C7	0.039 (1)	0.031 (1)	0.050 (1)	−0.016 (1)	−0.012 (1)	−0.001 (1)
C8	0.046 (1)	0.041 (1)	0.040 (1)	−0.021 (1)	−0.013 (1)	0.008 (1)

Geometric parameters (Å, º)

S1—O1	1.444 (1)	C3—C7	1.482 (2)
S1—O2	1.456 (1)	C4—C5	1.393 (2)
S1—O3	1.463 (1)	C5—C6	1.369 (3)
S1—C1	1.762 (2)	O4—H4o	0.84 (1)
O4—C7	1.315 (2)	O6—H6o	0.85 (1)
O5—C7	1.212 (2)	N1—H1n1	0.84 (1)
O6—C4	1.357 (2)	N1—H1n2	0.84 (1)
N1—C8	1.313 (2)	N2—H2n1	0.85 (1)
N2—C8	1.326 (2)	N2—H2n2	0.85 (1)
N3—C8	1.317 (2)	N3—H3n1	0.86 (1)
C1—C2	1.376 (2)	N3—H3n2	0.86 (1)
C1—C6	1.397 (2)	C2—H2	0.94 (1)
C2—C3	1.389 (2)	C5—H5	0.95 (1)
C3—C4	1.400 (2)	C6—H6	0.95 (1)
O1—S1—O2	113.2 (1)	N1—C8—N3	120.4 (2)
O1—S1—O3	112.3 (1)	N1—C8—N2	119.8 (2)
O2—S1—O3	111.8 (1)	N3—C8—N2	119.8 (2)
O1—S1—C1	106.6 (1)	C7—O4—H4o	116 (2)
O2—S1—C1	106.4 (1)	C4—O6—H6o	103 (2)
O3—S1—C1	105.9 (1)	C8—N1—H1n1	122 (2)
C2—C1—C6	120.0 (1)	C8—N1—H1n2	119 (2)
C2—C1—S1	120.3 (1)	H1n1—N1—H1n2	118 (2)
C6—C1—S1	119.7 (1)	C8—N2—H2n1	121 (2)
C1—C2—C3	120.6 (1)	C8—N2—H2n2	118 (2)
C2—C3—C4	119.2 (1)	H2n1—N2—H2n2	120 (2)
C2—C3—C7	121.3 (1)	C8—N3—H3n1	119 (2)
C4—C3—C7	119.5 (2)	C8—N3—H3n2	119 (2)
O6—C4—C5	118.1 (2)	H3n1—N3—H3n2	121 (2)
O6—C4—C3	122.1 (2)	C1—C2—H2	122 (1)
C5—C4—C3	119.9 (2)	C3—C2—H2	118 (1)
C6—C5—C4	120.3 (2)	C6—C5—H5	120 (1)
C5—C6—C1	120.1 (1)	C4—C5—H5	120 (1)
O5—C7—O4	123.9 (2)	C5—C6—H6	119 (1)
O5—C7—C3	123.3 (2)	C1—C6—H6	121 (1)
O4—C7—C3	112.8 (2)
O1—S1—C1—C2	103.6 (1)	C2—C3—C4—C5	0.0 (3)
O2—S1—C1—C2	−17.6 (2)	C7—C3—C4—C5	179.3 (2)
O3—S1—C1—C2	−136.7 (1)	O6—C4—C5—C6	179.2 (2)
O1—S1—C1—C6	−73.9 (2)	C3—C4—C5—C6	−0.5 (3)
O2—S1—C1—C6	165.0 (1)	C4—C5—C6—C1	0.5 (3)
O3—S1—C1—C6	45.9 (2)	C2—C1—C6—C5	0.0 (3)
C6—C1—C2—C3	−0.5 (3)	S1—C1—C6—C5	177.4 (1)
S1—C1—C2—C3	−177.9 (1)	C2—C3—C7—O5	−180.0 (2)
C1—C2—C3—C4	0.5 (2)	C4—C3—C7—O5	0.7 (3)
C1—C2—C3—C7	−178.8 (2)	C2—C3—C7—O4	0.0 (2)
C2—C3—C4—O6	−179.7 (2)	C4—C3—C7—O4	−179.3 (2)
C7—C3—C4—O6	−0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O3^i	0.84 (1)	1.78 (1)	2.611 (2)	171 (3)
O6—H6o···O5	0.85 (1)	1.80 (2)	2.601 (2)	155 (3)
N1—H1n2···O1	0.84 (1)	2.01 (1)	2.851 (2)	177 (2)
N1—H1n1···O3^ii	0.84 (1)	2.05 (1)	2.885 (2)	172 (2)
N2—H2n1···O2	0.85 (1)	2.16 (1)	2.988 (2)	166 (2)
N2—H2n2···O6^iii	0.85 (1)	2.52 (2)	3.246 (2)	143 (2)
N3—H3n1···O6^iii	0.86 (1)	2.19 (1)	3.006 (2)	159 (2)
N3—H3n2···O2^ii	0.86 (1)	2.13 (1)	2.949 (2)	160 (2)

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x, y, z−1.