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organic compounds
3-Aminopyridinium 4-hydroxy-3-iodonaphthalene-1-sulfonate dihydrate
aBasic Experiment Teaching Center, Henan University, Kaifeng 475001, People's Republic of China
*Correspondence e-mail: lijiehd@163.com
In the hydrated title salt, C5H7N2+·C10H6IO4S−·2H2O, the component species are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming an infinite three-dimensional framework.
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2001); cell SAINT-Plus (Bruker, 2001
); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: PLATON (Spek, 2003
); software used to prepare material for publication: PLATON.
Supporting information
10.1107/S1600536808014098/hb2719sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808014098/hb2719Isup2.hkl
A 5-ml ethanol solution of 3-aminopyridine (1.0 mmol, 0.094 g) was added to a 20-ml hot aqueous solution of 8-hydroxy-7-iodo-5-quinolinesulfonic acid (1.0 mmol, 0.351 g) and the mixture was stirred for 20 minutes at 373 K. Then the solution was filtered, and the filtrate was kept at the room temperature. After two weeks, yellow blocks of (I) were obtained.
The N- and O-bonded H atoms bonded were located in a difference synthesis and refined isotropically with N—H = 0.89 (1), O—H = 0.85 (1) and H···H = 1.34 (1) Å, respectively. All the remaining H atoms were placed in calculated positions, with C—H = 0.93Å and were refined as riding with Uiso = 1.2Ueq(C). This
scheme results in a short intramolecular H4···H6 contact of 1.71Å, although H4 participates in a plausible intermolecular hydrogen bond: thus the location of H4 should be regarded as less certain. Other placement schemes for H4 appear to lead to disordered hydrogen bond arrangements.Data collection: SMART (Bruker, 2001); cell
SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).C5H7N2+·C10H6IO4S−·2H2O | F(000) = 952 |
Mr = 480.27 | Dx = 1.799 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9093 reflections |
a = 15.0219 (6) Å | θ = 2.4–27.7° |
b = 6.9917 (3) Å | µ = 1.96 mm−1 |
c = 18.0729 (7) Å | T = 296 K |
β = 110.868 (1)° | Block, yellow |
V = 1773.66 (12) Å3 | 0.18 × 0.12 × 0.10 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 3484 independent reflections |
Radiation source: fine-focus sealed tube | 3128 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −18→18 |
Tmin = 0.720, Tmax = 0.828 | k = −8→8 |
17926 measured reflections | l = −22→22 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0364P)2 + 1.4355P] where P = (Fo2 + 2Fc2)/3 |
3484 reflections | (Δ/σ)max < 0.001 |
258 parameters | Δρmax = 0.71 e Å−3 |
34 restraints | Δρmin = −0.96 e Å−3 |
C5H7N2+·C10H6IO4S−·2H2O | V = 1773.66 (12) Å3 |
Mr = 480.27 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.0219 (6) Å | µ = 1.96 mm−1 |
b = 6.9917 (3) Å | T = 296 K |
c = 18.0729 (7) Å | 0.18 × 0.12 × 0.10 mm |
β = 110.868 (1)° |
Bruker SMART APEX CCD diffractometer | 3484 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3128 reflections with I > 2σ(I) |
Tmin = 0.720, Tmax = 0.828 | Rint = 0.027 |
17926 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 34 restraints |
wR(F2) = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.71 e Å−3 |
3484 reflections | Δρmin = −0.96 e Å−3 |
258 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.7208 (2) | 0.1965 (4) | −0.01736 (18) | 0.0486 (7) | |
H1A | 0.6708 (18) | 0.233 (5) | −0.0582 (16) | 0.056 (11)* | |
N2 | 0.7670 (2) | 0.0577 (5) | 0.18478 (18) | 0.0614 (8) | |
H2B | 0.7069 (11) | 0.034 (6) | 0.179 (2) | 0.065 (11)* | |
H2C | 0.8150 (18) | 0.008 (5) | 0.2246 (15) | 0.059 (10)* | |
C11 | 0.8061 (3) | 0.1948 (5) | −0.0234 (2) | 0.0564 (9) | |
H11A | 0.8135 | 0.2277 | −0.0708 | 0.068* | |
C12 | 0.8834 (2) | 0.1434 (5) | 0.0416 (2) | 0.0577 (9) | |
H12A | 0.9438 | 0.1405 | 0.0384 | 0.069* | |
C13 | 0.8718 (2) | 0.0965 (5) | 0.1112 (2) | 0.0541 (8) | |
H13A | 0.9245 | 0.0618 | 0.1550 | 0.065* | |
C14 | 0.7811 (2) | 0.1006 (4) | 0.11680 (19) | 0.0433 (7) | |
C15 | 0.7058 (2) | 0.1516 (4) | 0.0493 (2) | 0.0447 (7) | |
H15A | 0.6443 | 0.1547 | 0.0502 | 0.054* | |
S1 | 0.51967 (4) | 0.21097 (9) | 0.19020 (4) | 0.03081 (15) | |
I1 | 0.159514 (12) | 0.20253 (3) | 0.230170 (10) | 0.03822 (8) | |
O1 | 0.54976 (13) | 0.0659 (3) | 0.14622 (13) | 0.0469 (5) | |
O2 | 0.55842 (13) | 0.3982 (3) | 0.18257 (13) | 0.0469 (5) | |
O3 | 0.53822 (15) | 0.1580 (4) | 0.27109 (13) | 0.0570 (6) | |
O4 | 0.10004 (13) | 0.2998 (3) | 0.04865 (12) | 0.0393 (5) | |
H4 | 0.080 (3) | 0.315 (6) | −0.0008 (7) | 0.071 (13)* | |
C1 | 0.39401 (17) | 0.2327 (4) | 0.14385 (15) | 0.0273 (5) | |
C2 | 0.33925 (18) | 0.2092 (3) | 0.18943 (15) | 0.0285 (5) | |
H2A | 0.3682 | 0.1784 | 0.2427 | 0.034* | |
C3 | 0.24002 (18) | 0.2308 (4) | 0.15712 (15) | 0.0281 (5) | |
C4 | 0.19533 (17) | 0.2770 (3) | 0.07873 (15) | 0.0275 (5) | |
C5 | 0.25099 (18) | 0.3043 (3) | 0.03008 (15) | 0.0275 (5) | |
C6 | 0.20225 (16) | 0.3533 (3) | −0.04661 (13) | 0.0230 (5) | |
H6 | 0.1364 | 0.3671 | −0.0655 | 0.028* | |
C7 | 0.2508 (2) | 0.3803 (4) | −0.09292 (16) | 0.0399 (6) | |
H7 | 0.2179 | 0.4140 | −0.1454 | 0.048* | |
C8 | 0.3502 (2) | 0.3611 (5) | −0.06744 (17) | 0.0423 (7) | |
H8 | 0.3818 | 0.3819 | −0.1027 | 0.051* | |
C9 | 0.4003 (2) | 0.3120 (4) | 0.00897 (17) | 0.0371 (6) | |
H9 | 0.4661 | 0.2985 | 0.0262 | 0.045* | |
C10 | 0.35128 (18) | 0.2815 (3) | 0.06225 (15) | 0.0275 (5) | |
O1W | −0.02157 (17) | 0.3572 (4) | −0.09765 (13) | 0.0532 (6) | |
H1WA | −0.038 (2) | 0.473 (2) | −0.095 (2) | 0.060 (5)* | |
H1WB | 0.002 (2) | 0.359 (4) | −0.1337 (16) | 0.056 (5)* | |
O2W | 0.55451 (16) | 0.2736 (3) | −0.13855 (17) | 0.0555 (6) | |
H2WA | 0.5162 (18) | 0.179 (3) | −0.147 (2) | 0.059 (11)* | |
H2WB | 0.5167 (18) | 0.370 (3) | −0.151 (2) | 0.072 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0482 (16) | 0.0385 (14) | 0.0518 (16) | −0.0003 (12) | 0.0091 (13) | 0.0011 (12) |
N2 | 0.0386 (16) | 0.090 (2) | 0.0548 (17) | 0.0127 (16) | 0.0150 (14) | 0.0124 (16) |
C11 | 0.063 (2) | 0.0483 (19) | 0.064 (2) | −0.0091 (16) | 0.0302 (19) | 0.0008 (16) |
C12 | 0.0395 (17) | 0.060 (2) | 0.080 (3) | −0.0068 (15) | 0.0282 (18) | 0.0007 (19) |
C13 | 0.0307 (15) | 0.058 (2) | 0.068 (2) | 0.0012 (14) | 0.0112 (15) | 0.0044 (17) |
C14 | 0.0321 (14) | 0.0431 (16) | 0.0531 (17) | 0.0027 (12) | 0.0129 (13) | −0.0010 (14) |
C15 | 0.0316 (14) | 0.0430 (16) | 0.0580 (19) | 0.0040 (12) | 0.0142 (14) | 0.0016 (14) |
S1 | 0.0198 (3) | 0.0380 (3) | 0.0329 (3) | 0.0003 (2) | 0.0073 (2) | 0.0048 (3) |
I1 | 0.03151 (12) | 0.05175 (14) | 0.03694 (12) | 0.00166 (7) | 0.01898 (8) | 0.00622 (8) |
O1 | 0.0299 (10) | 0.0489 (12) | 0.0630 (13) | 0.0051 (9) | 0.0180 (9) | −0.0058 (10) |
O2 | 0.0289 (10) | 0.0424 (11) | 0.0616 (13) | −0.0083 (9) | 0.0066 (9) | 0.0054 (10) |
O3 | 0.0303 (11) | 0.0986 (19) | 0.0378 (11) | 0.0063 (11) | 0.0069 (9) | 0.0226 (12) |
O4 | 0.0214 (9) | 0.0645 (14) | 0.0313 (11) | 0.0048 (8) | 0.0084 (8) | 0.0037 (9) |
C1 | 0.0206 (11) | 0.0297 (12) | 0.0318 (13) | 0.0004 (9) | 0.0095 (10) | 0.0015 (10) |
C2 | 0.0258 (12) | 0.0323 (13) | 0.0261 (12) | 0.0011 (10) | 0.0078 (10) | 0.0036 (10) |
C3 | 0.0249 (12) | 0.0336 (13) | 0.0297 (12) | −0.0003 (10) | 0.0144 (10) | 0.0007 (10) |
C4 | 0.0214 (12) | 0.0318 (12) | 0.0297 (12) | 0.0013 (10) | 0.0095 (10) | −0.0014 (10) |
C5 | 0.0255 (12) | 0.0278 (12) | 0.0296 (12) | −0.0006 (9) | 0.0101 (10) | −0.0019 (9) |
C6 | 0.0162 (10) | 0.0326 (12) | 0.0178 (10) | 0.0005 (9) | 0.0030 (8) | 0.0016 (9) |
C7 | 0.0390 (15) | 0.0479 (16) | 0.0289 (13) | −0.0033 (13) | 0.0075 (11) | 0.0030 (12) |
C8 | 0.0375 (15) | 0.0600 (18) | 0.0342 (14) | −0.0037 (14) | 0.0188 (12) | 0.0049 (13) |
C9 | 0.0274 (13) | 0.0495 (16) | 0.0362 (14) | −0.0016 (12) | 0.0135 (12) | 0.0028 (12) |
C10 | 0.0248 (12) | 0.0285 (12) | 0.0288 (12) | −0.0015 (9) | 0.0092 (10) | −0.0006 (10) |
O1W | 0.0462 (12) | 0.0741 (16) | 0.0393 (12) | 0.0129 (12) | 0.0151 (10) | 0.0012 (11) |
O2W | 0.0377 (12) | 0.0424 (13) | 0.0792 (18) | 0.0006 (10) | 0.0122 (12) | −0.0025 (12) |
N1—C11 | 1.325 (5) | C1—C2 | 1.366 (4) |
N1—C15 | 1.339 (4) | C1—C10 | 1.424 (4) |
N1—H1A | 0.882 (10) | C2—C3 | 1.402 (4) |
N2—C14 | 1.353 (4) | C2—H2A | 0.9300 |
N2—H2B | 0.886 (10) | C3—C4 | 1.373 (4) |
N2—H2C | 0.888 (10) | C4—C5 | 1.425 (4) |
C11—C12 | 1.374 (5) | C5—C6 | 1.361 (3) |
C11—H11A | 0.9300 | C5—C10 | 1.417 (4) |
C12—C13 | 1.369 (5) | C6—C7 | 1.305 (4) |
C12—H12A | 0.9300 | C6—H6 | 0.9300 |
C13—C14 | 1.403 (4) | C7—C8 | 1.404 (4) |
C13—H13A | 0.9300 | C7—H7 | 0.9300 |
C14—C15 | 1.382 (4) | C8—C9 | 1.360 (4) |
C15—H15A | 0.9300 | C8—H8 | 0.9300 |
S1—O3 | 1.436 (2) | C9—C10 | 1.421 (4) |
S1—O1 | 1.456 (2) | C9—H9 | 0.9300 |
S1—O2 | 1.459 (2) | O1W—H1WA | 0.851 (10) |
S1—C1 | 1.778 (2) | O1W—H1WB | 0.847 (10) |
I1—C3 | 2.093 (2) | O2W—H2WA | 0.853 (10) |
O4—C4 | 1.347 (3) | O2W—H2WB | 0.856 (10) |
O4—H4 | 0.843 (10) | ||
C11—N1—C15 | 123.4 (3) | C10—C1—S1 | 121.29 (19) |
C11—N1—H1A | 120 (3) | C1—C2—C3 | 121.0 (2) |
C15—N1—H1A | 117 (3) | C1—C2—H2A | 119.5 |
C14—N2—H2B | 115 (2) | C3—C2—H2A | 119.5 |
C14—N2—H2C | 119 (2) | C4—C3—C2 | 120.8 (2) |
H2B—N2—H2C | 122 (4) | C4—C3—I1 | 119.55 (18) |
N1—C11—C12 | 118.6 (4) | C2—C3—I1 | 119.64 (19) |
N1—C11—H11A | 120.7 | O4—C4—C3 | 120.2 (2) |
C12—C11—H11A | 120.7 | O4—C4—C5 | 120.5 (2) |
C13—C12—C11 | 120.3 (3) | C3—C4—C5 | 119.3 (2) |
C13—C12—H12A | 119.9 | C6—C5—C10 | 123.6 (2) |
C11—C12—H12A | 119.9 | C6—C5—C4 | 116.2 (2) |
C12—C13—C14 | 120.4 (3) | C10—C5—C4 | 120.2 (2) |
C12—C13—H13A | 119.8 | C7—C6—C5 | 118.0 (2) |
C14—C13—H13A | 119.8 | C7—C6—H6 | 121.0 |
N2—C14—C15 | 121.0 (3) | C5—C6—H6 | 121.0 |
N2—C14—C13 | 122.1 (3) | C6—C7—C8 | 123.2 (3) |
C15—C14—C13 | 116.9 (3) | C6—C7—H7 | 118.4 |
N1—C15—C14 | 120.5 (3) | C8—C7—H7 | 118.4 |
N1—C15—H15A | 119.8 | C9—C8—C7 | 119.7 (3) |
C14—C15—H15A | 119.8 | C9—C8—H8 | 120.1 |
O3—S1—O1 | 113.00 (15) | C7—C8—H8 | 120.1 |
O3—S1—O2 | 112.85 (15) | C8—C9—C10 | 119.6 (3) |
O1—S1—O2 | 111.19 (13) | C8—C9—H9 | 120.2 |
O3—S1—C1 | 106.86 (12) | C10—C9—H9 | 120.2 |
O1—S1—C1 | 106.64 (12) | C5—C10—C9 | 115.9 (2) |
O2—S1—C1 | 105.73 (12) | C5—C10—C1 | 118.2 (2) |
C4—O4—H4 | 111 (3) | C9—C10—C1 | 125.9 (2) |
C2—C1—C10 | 120.5 (2) | H1WA—O1W—H1WB | 103.8 (15) |
C2—C1—S1 | 118.17 (19) | H2WA—O2W—H2WB | 102.6 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2W | 0.88 (1) | 1.85 (1) | 2.725 (4) | 170 (4) |
N2—H2B···O1 | 0.89 (1) | 2.23 (2) | 3.085 (3) | 162 (4) |
N2—H2C···O2i | 0.89 (1) | 2.18 (1) | 3.064 (4) | 175 (3) |
O4—H4···O1W | 0.84 (1) | 1.89 (2) | 2.655 (3) | 150 (4) |
O1W—H1WB···O3ii | 0.85 (1) | 1.98 (1) | 2.822 (3) | 171 (4) |
O1W—H1WA···O4iii | 0.85 (1) | 2.16 (2) | 2.944 (3) | 153 (3) |
O2W—H2WA···O1iv | 0.85 (1) | 1.98 (1) | 2.820 (3) | 167 (3) |
O2W—H2WB···O2v | 0.86 (1) | 1.94 (1) | 2.796 (3) | 173 (3) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C5H7N2+·C10H6IO4S−·2H2O |
Mr | 480.27 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 15.0219 (6), 6.9917 (3), 18.0729 (7) |
β (°) | 110.868 (1) |
V (Å3) | 1773.66 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.96 |
Crystal size (mm) | 0.18 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.720, 0.828 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17926, 3484, 3128 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.069, 1.08 |
No. of reflections | 3484 |
No. of parameters | 258 |
No. of restraints | 34 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.71, −0.96 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2W | 0.882 (10) | 1.853 (13) | 2.725 (4) | 170 (4) |
N2—H2B···O1 | 0.886 (10) | 2.232 (16) | 3.085 (3) | 162 (4) |
N2—H2C···O2i | 0.888 (10) | 2.179 (11) | 3.064 (4) | 175 (3) |
O4—H4···O1W | 0.843 (10) | 1.89 (2) | 2.655 (3) | 150 (4) |
O1W—H1WB···O3ii | 0.847 (10) | 1.983 (12) | 2.822 (3) | 171 (4) |
O1W—H1WA···O4iii | 0.851 (10) | 2.158 (15) | 2.944 (3) | 153 (3) |
O2W—H2WA···O1iv | 0.853 (10) | 1.981 (12) | 2.820 (3) | 167 (3) |
O2W—H2WB···O2v | 0.856 (10) | 1.944 (11) | 2.796 (3) | 173 (3) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z. |
References
Bruker (2001). SADABS, SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Li, J. (2007). Acta Cryst. E63, o4171. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
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This work continues our previous synthetic and structural studies of the hydrogen bonding interactions between various organic acids and substituted pyridines (Li, 2007).
The asymmetric unit of the title salt, (I), is composed of one 3-aminopyridinium cation, one 8-hydroxy-7-iodo-5-quinolinesulfonate anion and two water molecules (Fig. 1). One water molecule (O1W), acting as a hydrogen bonding donor interacts with the hydroxy oxygen (O4) acting as hydrogen bonding acceptor (Table 1). The other water molecule (O2W) and the 3-aminopyridinium cation are linked by a N1—H1A···O2W hydrogen bond. Moreover, the cation and anion are linked together by a N2—H2B···O1 hydrogen bond. Overall, an infinite three-dimensional framework results (Fig. 2).