Bis(2-hydroxy­pyridinium) naphthalene-1,5-disulfonate dihydrate

The cation, anion and water molecules of the title compound, 2C₅H₆NO⁺·C₁₀H₆O₆S₂^2-·2H₂O, interact via hydrogen bonds, giving rise to a tight three-dimensional network structure. Two independent anions both lie on centers of inversion, and the asymmetric unit consists of two half-anions, two independent cations and two independent water molecules.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.123
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving .   ?
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2W2   ..  H7O     ..       2.08 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.10
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1W2   ..  H8O     ..       2.10 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT736_ALERT_1_C H...A   Calc     2.06(3), Rep   2.060(10) ......       3.00 su-Rat
              H2#  -O5      1.555   4.566

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   4 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

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.

Bis(2-hydroxypyridinium) naphthalene-1,5-disulfonate dihydrate

Crystal data

2C5H6NO^+·C10H6O6S2^2^−·2H2O	F(000) = 1072
Mr = 514.52	Dx = 1.525 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16290 reflections
a = 14.740 (3) Å	θ = 3.3–27.4°
b = 10.883 (2) Å	µ = 0.30 mm^−1
c = 14.075 (3) Å	T = 295 K
β = 96.91 (3)°	Prism, colorless
V = 2241.7 (8) Å^3	0.42 × 0.31 × 0.24 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	5082 independent reflections
Radiation source: fine-focus sealed tube	3742 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.797, Tmax = 0.932	k = −14→12
20659 measured reflections	l = −18→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0679P)^2 + 0.5447P] where P = (Fo^2 + 2Fc^2)/3
5082 reflections	(Δ/σ)max = 0.001
339 parameters	Δρmax = 0.44 e Å^−3
10 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.86407 (3)	0.56595 (5)	0.78973 (3)	0.0396 (1)
S2	0.63667 (3)	0.44727 (5)	0.21166 (3)	0.0384 (1)
O1	0.8459 (1)	0.4414 (2)	0.7560 (1)	0.0586 (4)
O2	0.9377 (1)	0.6254 (2)	0.7484 (1)	0.0569 (4)
O3	0.7830 (1)	0.6420 (2)	0.7813 (1)	0.0549 (4)
O4	0.7332 (1)	0.4222 (2)	0.2218 (1)	0.0602 (5)
O5	0.5859 (1)	0.3417 (1)	0.2418 (1)	0.0509 (4)
O6	0.6149 (1)	0.5608 (2)	0.2566 (1)	0.0589 (4)
O7	0.8994 (1)	0.6142 (2)	0.4897 (1)	0.0512 (4)
O8	0.6127 (1)	0.3574 (2)	0.5020 (1)	0.0518 (4)
O1w	0.6684 (1)	0.3768 (2)	0.6800 (1)	0.0638 (5)
O2w	0.8328 (1)	0.6143 (2)	0.3171 (1)	0.0651 (5)
N1	1.0234 (1)	0.6533 (2)	0.5908 (1)	0.0420 (4)
N2	0.4883 (1)	0.3353 (2)	0.3961 (1)	0.0414 (4)
C1	0.9018 (1)	0.5562 (2)	0.9147 (1)	0.0319 (4)
C2	0.8464 (1)	0.6035 (2)	0.9762 (1)	0.0388 (4)
C3	0.8727 (1)	0.5998 (2)	1.0752 (1)	0.0423 (5)
C4	0.9534 (1)	0.5501 (2)	1.1116 (1)	0.0377 (4)
C5	1.0131 (1)	0.4988 (2)	1.0504 (1)	0.0302 (4)
C6	0.6022 (1)	0.4623 (2)	0.0866 (1)	0.0307 (4)
C7	0.6659 (1)	0.4403 (2)	0.0262 (1)	0.0379 (4)
C8	0.6426 (1)	0.4502 (2)	−0.0731 (1)	0.0412 (5)
C9	0.5568 (1)	0.4811 (2)	−0.1107 (1)	0.0362 (4)
C10	0.4887 (1)	0.5046 (2)	−0.0507 (1)	0.0292 (4)
C11	0.9853 (1)	0.6474 (2)	0.5005 (2)	0.0392 (4)
C12	1.0378 (2)	0.6738 (2)	0.4277 (2)	0.0493 (5)
C13	1.1275 (2)	0.7024 (2)	0.4521 (2)	0.0576 (6)
C14	1.1654 (2)	0.7050 (2)	0.5471 (2)	0.0575 (6)
C15	1.1115 (2)	0.6814 (2)	0.6156 (2)	0.0505 (5)
C16	0.5239 (1)	0.3432 (2)	0.4878 (1)	0.0375 (4)
C17	0.4659 (1)	0.3384 (2)	0.5579 (1)	0.0454 (5)
C18	0.3748 (2)	0.3278 (2)	0.5307 (2)	0.0538 (6)
C19	0.3399 (2)	0.3211 (2)	0.4347 (2)	0.0553 (6)
C20	0.3983 (2)	0.3245 (2)	0.3686 (2)	0.0494 (5)
H1n	0.990 (1)	0.635 (2)	0.635 (1)	0.06 (1)*
H2n	0.525 (1)	0.341 (2)	0.355 (1)	0.06 (1)*
H7o	0.876 (2)	0.615 (3)	0.431 (1)	0.08 (1)*
H8o	0.631 (2)	0.362 (3)	0.562 (1)	0.07 (1)*
H1w1	0.720 (1)	0.405 (2)	0.703 (2)	0.07 (1)*
H1w2	0.661 (2)	0.307 (2)	0.705 (2)	0.10 (1)*
H2w1	0.797 (1)	0.559 (1)	0.293 (2)	0.07 (1)*
H2w2	0.810 (2)	0.685 (1)	0.304 (2)	0.06 (1)*
H2	0.7908	0.6385	0.9523	0.047*
H3	0.8340	0.6321	1.1164	0.051*
H4	0.9700	0.5494	1.1775	0.045*
H7	0.7251	0.4186	0.0508	0.046*
H8	0.6867	0.4354	−0.1136	0.049*
H9	0.5426	0.4868	−0.1768	0.043*
H12	1.0125	0.6720	0.3640	0.059*
H13	1.1638	0.7205	0.4043	0.069*
H14	1.2271	0.7228	0.5632	0.069*
H15	1.1353	0.6846	0.6798	0.061*
H17	0.4888	0.3423	0.6224	0.054*
H18	0.3349	0.3249	0.5771	0.065*
H19	0.2773	0.3144	0.4166	0.066*
H20	0.3765	0.3194	0.3039	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0382 (3)	0.0513 (3)	0.0265 (2)	−0.0043 (2)	−0.0072 (2)	0.0034 (1)
S2	0.0375 (3)	0.0512 (3)	0.0248 (2)	−0.0028 (2)	−0.0035 (2)	0.0000 (2)
O1	0.068 (1)	0.059 (1)	0.043 (1)	−0.004 (1)	−0.0173 (7)	−0.009 (1)
O2	0.053 (1)	0.084 (1)	0.033 (1)	−0.010 (1)	0.0032 (7)	0.014 (1)
O3	0.046 (1)	0.069 (1)	0.045 (1)	0.007 (1)	−0.0142 (7)	0.008 (1)
O4	0.041 (1)	0.095 (1)	0.042 (1)	0.006 (1)	−0.0075 (7)	0.006 (1)
O5	0.064 (1)	0.059 (1)	0.030 (1)	−0.010 (1)	0.0069 (7)	0.006 (1)
O6	0.077 (1)	0.060 (1)	0.036 (1)	0.001 (1)	−0.0066 (7)	−0.016 (1)
O7	0.043 (1)	0.059 (1)	0.050 (1)	−0.007 (1)	−0.0039 (7)	0.002 (1)
O8	0.040 (1)	0.068 (1)	0.047 (1)	−0.002 (1)	0.0008 (7)	0.004 (1)
O1w	0.064 (1)	0.070 (1)	0.052 (1)	−0.020 (1)	−0.013 (1)	0.005 (1)
O2w	0.069 (1)	0.062 (1)	0.056 (1)	−0.016 (1)	−0.023 (1)	0.001 (1)
N1	0.045 (1)	0.045 (1)	0.036 (1)	0.001 (1)	0.004 (1)	0.000 (1)
N2	0.046 (1)	0.047 (1)	0.031 (1)	−0.003 (1)	0.005 (1)	0.001 (1)
C1	0.031 (1)	0.039 (1)	0.025 (1)	−0.006 (1)	−0.003 (1)	0.002 (1)
C2	0.032 (1)	0.048 (1)	0.036 (1)	0.001 (1)	0.002 (1)	0.004 (1)
C3	0.039 (1)	0.054 (1)	0.035 (1)	0.006 (1)	0.009 (1)	0.000 (1)
C4	0.040 (1)	0.049 (1)	0.025 (1)	−0.001 (1)	0.004 (1)	0.000 (1)
C5	0.030 (1)	0.035 (1)	0.025 (1)	−0.006 (1)	0.000 (1)	0.002 (1)
C6	0.032 (1)	0.035 (1)	0.025 (1)	−0.002 (1)	0.002 (1)	0.000 (1)
C7	0.029 (1)	0.050 (1)	0.034 (1)	0.001 (1)	0.002 (1)	0.001 (1)
C8	0.034 (1)	0.059 (1)	0.032 (1)	0.003 (1)	0.011 (1)	−0.002 (1)
C9	0.038 (1)	0.048 (1)	0.023 (1)	0.000 (1)	0.006 (1)	0.000 (1)
C10	0.031 (1)	0.032 (1)	0.025 (1)	−0.004 (1)	0.003 (1)	−0.002 (1)
C11	0.041 (1)	0.035 (1)	0.040 (1)	0.002 (1)	0.000 (1)	−0.001 (1)
C12	0.060 (1)	0.053 (1)	0.034 (1)	0.001 (1)	0.001 (1)	0.000 (1)
C13	0.054 (1)	0.066 (2)	0.056 (1)	−0.004 (1)	0.020 (1)	−0.002 (1)
C14	0.039 (1)	0.065 (2)	0.067 (2)	−0.007 (1)	0.003 (1)	−0.007 (1)
C15	0.051 (1)	0.052 (1)	0.045 (1)	0.001 (1)	−0.009 (1)	−0.006 (1)
C16	0.040 (1)	0.035 (1)	0.037 (1)	−0.001 (1)	0.002 (1)	0.001 (1)
C17	0.049 (1)	0.056 (1)	0.031 (1)	−0.001 (1)	0.003 (1)	−0.003 (1)
C18	0.047 (1)	0.070 (2)	0.046 (1)	−0.007 (1)	0.012 (1)	−0.004 (1)
C19	0.042 (1)	0.065 (2)	0.056 (1)	−0.010 (1)	−0.001 (1)	−0.003 (1)
C20	0.055 (1)	0.054 (1)	0.036 (1)	−0.009 (1)	−0.006 (1)	−0.002 (1)

Geometric parameters (Å, º)

S1—O1	1.450 (2)	C12—C13	1.361 (3)
S1—O2	1.444 (2)	C13—C14	1.386 (3)
S1—O3	1.447 (2)	C14—C15	1.346 (3)
S1—C1	1.784 (2)	C16—C17	1.383 (3)
S2—O4	1.438 (2)	C17—C18	1.357 (3)
S2—O5	1.462 (2)	C18—C19	1.388 (3)
S2—O6	1.441 (2)	C19—C20	1.342 (3)
S2—C6	1.780 (2)	O7—H7o	0.86 (1)
O7—C11	1.307 (2)	O8—H8o	0.85 (1)
O8—C16	1.308 (2)	O1w—H1w1	0.85 (1)
N1—C11	1.328 (3)	O1w—H1w2	0.85 (1)
N1—C15	1.339 (3)	O2w—H2w1	0.85 (1)
N2—C16	1.336 (2)	O2w—H2w2	0.85 (1)
N2—C20	1.341 (3)	N1—H1n	0.86 (1)
C1—C2	1.360 (3)	N2—H2n	0.85 (1)
C1—C5^i	1.423 (2)	C2—H2	0.93
C2—C3	1.402 (3)	C3—H3	0.93
C3—C4	1.351 (3)	C4—H4	0.93
C4—C5	1.417 (2)	C7—H7	0.93
C5—C1^i	1.423 (2)	C8—H8	0.93
C5—C5^i	1.426 (3)	C9—H9	0.93
C6—C7	1.363 (2)	C12—H12	0.93
C6—C10^ii	1.420 (2)	C13—H13	0.93
C7—C8	1.402 (3)	C14—H14	0.93
C8—C9	1.353 (3)	C15—H15	0.93
C9—C10	1.412 (2)	C17—H17	0.93
C10—C6^ii	1.420 (2)	C18—H18	0.93
C10—C10^ii	1.429 (3)	C19—H19	0.93
C11—C12	1.387 (3)	C20—H20	0.93
O1—S1—O2	113.9 (1)	C18—C17—C16	118.5 (2)
O1—S1—O3	112.9 (1)	C17—C18—C19	121.2 (2)
O1—S1—C1	106.9 (1)	C20—C19—C18	118.7 (2)
O2—S1—O3	111.3 (1)	N2—C20—C19	119.7 (2)
O2—S1—C1	105.3 (1)	C11—O7—H7o	112 (2)
O3—S1—C1	105.8 (1)	C16—O8—H8o	111 (2)
O4—S2—O5	110.9 (1)	H1w1—O1w—H1w2	108 (2)
O4—S2—O6	112.9 (1)	H2w1—O2w—H2w2	110 (2)
O4—S2—C6	106.1 (1)	C11—N1—C15	123.2 (2)
O5—S2—O6	113.5 (1)	C11—N1—H1n	118 (2)
O5—S2—C6	105.3 (1)	C15—N1—H1n	119 (2)
O6—S2—C6	107.6 (1)	C16—N2—H2n	117 (2)
C16—N2—C20	123.1 (2)	C20—N2—H2n	120 (2)
C2—C1—C5^i	120.8 (2)	C1—C2—H2	119.8
C2—C1—S1	117.7 (1)	C3—C2—H2	119.8
C5^i—C1—S1	121.5 (1)	C4—C3—H3	119.5
C1—C2—C3	120.5 (2)	C2—C3—H3	119.5
C4—C3—C2	120.9 (2)	C3—C4—H4	119.7
C3—C4—C5	120.7 (2)	C5—C4—H4	119.7
C4—C5—C1^i	122.8 (2)	C6—C7—H7	119.9
C4—C5—C5^i	119.0 (2)	C8—C7—H7	119.9
C1^i—C5—C5^i	118.2 (2)	C9—C8—H8	119.5
C7—C6—C10^ii	120.9 (2)	C7—C8—H8	119.5
C7—C6—S2	117.7 (1)	C8—C9—H9	119.7
C10^ii—C6—S2	121.4 (1)	C10—C9—H9	119.7
C6—C7—C8	120.2 (2)	C13—C12—H12	120.9
C9—C8—C7	121.0 (2)	C11—C12—H12	120.9
C8—C9—C10	120.6 (2)	C12—C13—H13	119.5
C9—C10—C6^ii	122.7 (2)	C14—C13—H13	119.5
C9—C10—C10^ii	119.2 (2)	C15—C14—H14	120.6
C6^ii—C10—C10^ii	118.1 (2)	C13—C14—H14	120.6
O7—C11—N1	114.7 (2)	N1—C15—H15	120.2
O7—C11—C12	126.2 (2)	C14—C15—H15	120.2
N1—C11—C12	119.1 (2)	C18—C17—H17	120.7
C13—C12—C11	118.2 (2)	C16—C17—H17	120.7
C12—C13—C14	121.0 (2)	C17—C18—H18	119.4
C15—C14—C13	118.9 (2)	C19—C18—H18	119.4
N1—C15—C14	119.6 (2)	C20—C19—H19	120.6
O8—C16—N2	115.1 (2)	C18—C19—H19	120.6
O8—C16—C17	126.1 (2)	N2—C20—H20	120.1
N2—C16—C17	118.8 (2)	C19—C20—H20	120.1
O2—S1—C1—C2	125.9 (2)	C6—C7—C8—C9	−0.3 (3)
O3—S1—C1—C2	8.0 (2)	C7—C8—C9—C10	0.3 (3)
O1—S1—C1—C2	−112.6 (2)	C8—C9—C10—C6^ii	179.8 (2)
O2—S1—C1—C5^i	−53.9 (2)	C8—C9—C10—C10^ii	−0.1 (3)
O3—S1—C1—C5^i	−171.9 (1)	C15—N1—C11—O7	177.6 (2)
O1—S1—C1—C5^i	67.6 (2)	C15—N1—C11—C12	−1.3 (3)
C5^i—C1—C2—C3	0.5 (3)	O7—C11—C12—C13	−177.5 (2)
S1—C1—C2—C3	−179.3 (2)	N1—C11—C12—C13	1.3 (3)
C1—C2—C3—C4	0.4 (3)	C11—C12—C13—C14	0.1 (4)
C2—C3—C4—C5	−0.8 (3)	C12—C13—C14—C15	−1.5 (4)
C3—C4—C5—C1^i	−179.1 (2)	C11—N1—C15—C14	−0.1 (3)
C3—C4—C5—C5^i	0.3 (3)	C13—C14—C15—N1	1.5 (4)
O4—S2—C6—C7	4.4 (2)	C20—N2—C16—O8	−177.8 (2)
O6—S2—C6—C7	125.5 (2)	C20—N2—C16—C17	1.0 (3)
O5—S2—C6—C7	−113.2 (2)	O8—C16—C17—C18	177.6 (2)
O4—S2—C6—C10^ii	−175.9 (2)	N2—C16—C17—C18	−1.1 (3)
O6—S2—C6—C10^ii	−54.8 (2)	C16—C17—C18—C19	0.4 (4)
O5—S2—C6—C10^ii	66.5 (2)	C17—C18—C19—C20	0.4 (4)
C10^ii—C6—C7—C8	0.1 (3)	C16—N2—C20—C19	−0.1 (3)
S2—C6—C7—C8	179.8 (2)	C18—C19—C20—N2	−0.6 (4)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7o···O2w	0.86 (1)	1.65 (1)	2.509 (2)	179 (3)
O8—H8o···O1w	0.85 (1)	1.70 (1)	2.550 (2)	178 (3)
O1w—H1w1···O1	0.85 (1)	1.95 (1)	2.794 (2)	170 (2)
O1w—H1w2···O5^iii	0.85 (1)	2.06 (1)	2.854 (3)	154 (2)
O2w—H2w1···O4	0.85 (1)	1.97 (1)	2.803 (2)	168 (3)
O2w—H2w2···O3^iv	0.85 (1)	1.95 (1)	2.782 (3)	168 (2)
N1—H1n···O2	0.86 (1)	1.86 (1)	2.700 (2)	165 (2)
N2—H2n···O5	0.85 (1)	1.92 (1)	2.748 (2)	167 (2)

Symmetry codes: (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.