Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046740/hb2550sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046740/hb2550Isup2.hkl |
CCDC reference: 663845
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.116
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A 5-ml ethanol soloution of 3-aminopyridine (1.0 mmol, 0.094 g) was added to an aqueous solution (25 ml) of 3,5-dinitrobenzoic acid (1.0 mmol, 0.210 g). The mixture was stirred for 10 minutes at 373 K. The solution was filtered, and the filtrate was kept at room temperature. After a week, yellow crystals of (I) were obtained.
The crystal symmetry is monoclinic. No plausible structural models could be developed assuming orthorhombic symmetry.
The pyridine N-bound and water H atoms were located in a difference map and were refined with N—H = 0.86 (1) Å, O—H = 0.82 (1) Å and H···H = 1.39 (1) Å. The remaining H atoms were positioned geometrically with C—H = 0.93 Å and N—H = 0.86 Å, and were refined as riding with Uiso(H) = 1.2Ueq(C or N) and Uiso(H) = 1.5Ueq(0).
This work continues our previous synthetic and structural studies of supramolecular salts (Wang & Wei, 2007). Herein we present the crystal structure of the title salt, (I).
The title salt contains one 3-aminopyridinium cation, one 3,5-dinitrobenzoate anion and one crystallization water molecule. These components are connected by N—H···O and O—H···O hydrogen bonds, in which the water oxygen atom, two nitrogen atoms of 3-aminopyridinium cation act as the hydrogen-bond acceptor and 3-aminopyridinium cation acts as the hydrogen-bond donor (Table 1). This results in an infinite two-dimensional network runing parallel to the plane (102) (Fig. 2).
For a related structure, see: Wang & Wei (2007).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
C5H7N2+·C7H3N2O6−·H2O | F(000) = 672 |
Mr = 324.26 | Dx = 1.533 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2386 reflections |
a = 8.904 (2) Å | θ = 2.3–26° |
b = 7.0683 (16) Å | µ = 0.13 mm−1 |
c = 22.331 (5) Å | T = 298 K |
β = 90.002 (3)° | Block, yellow |
V = 1405.3 (5) Å3 | 0.40 × 0.11 × 0.09 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2743 independent reflections |
Radiation source: fine-focus sealed tube | 2110 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −10→10 |
Tmin = 0.950, Tmax = 0.989 | k = −8→8 |
7329 measured reflections | l = −14→27 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2499P] where P = (Fo2 + 2Fc2)/3 |
2743 reflections | (Δ/σ)max < 0.001 |
220 parameters | Δρmax = 0.23 e Å−3 |
16 restraints | Δρmin = −0.18 e Å−3 |
C5H7N2+·C7H3N2O6−·H2O | V = 1405.3 (5) Å3 |
Mr = 324.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.904 (2) Å | µ = 0.13 mm−1 |
b = 7.0683 (16) Å | T = 298 K |
c = 22.331 (5) Å | 0.40 × 0.11 × 0.09 mm |
β = 90.002 (3)° |
Bruker SMART APEX CCD diffractometer | 2743 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 2110 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.989 | Rint = 0.022 |
7329 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 16 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.23 e Å−3 |
2743 reflections | Δρmin = −0.18 e Å−3 |
220 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 | ||
C1 | 0.37418 (18) | 0.5123 (2) | 0.56099 (7) | 0.0332 (4) | |
C2 | 0.39107 (18) | 0.3634 (2) | 0.60046 (8) | 0.0355 (4) | |
H2 | 0.3353 | 0.2532 | 0.5957 | 0.043* | |
C3 | 0.49144 (19) | 0.3802 (2) | 0.64695 (8) | 0.0366 (4) | |
C4 | 0.57995 (19) | 0.5379 (2) | 0.65486 (8) | 0.0389 (4) | |
H4 | 0.6487 | 0.5459 | 0.6861 | 0.047* | |
C5 | 0.56233 (19) | 0.6822 (2) | 0.61467 (8) | 0.0372 (4) | |
C6 | 0.46031 (19) | 0.6747 (2) | 0.56834 (8) | 0.0369 (4) | |
H6 | 0.4492 | 0.7767 | 0.5424 | 0.044* | |
C7 | 0.26189 (19) | 0.4982 (2) | 0.51025 (7) | 0.0349 (4) | |
N1 | 0.50348 (18) | 0.2256 (2) | 0.69057 (7) | 0.0469 (4) | |
N2 | 0.65549 (18) | 0.8523 (2) | 0.62170 (8) | 0.0508 (4) | |
O1 | 0.23633 (16) | 0.64928 (17) | 0.48228 (6) | 0.0499 (4) | |
O2 | 0.20429 (15) | 0.34363 (17) | 0.49949 (6) | 0.0480 (4) | |
O3 | 0.41038 (18) | 0.1002 (2) | 0.68925 (7) | 0.0700 (5) | |
O4 | 0.60686 (18) | 0.2298 (2) | 0.72611 (7) | 0.0693 (5) | |
O5 | 0.74764 (18) | 0.8530 (2) | 0.66225 (8) | 0.0729 (5) | |
O6 | 0.63675 (19) | 0.9837 (2) | 0.58748 (8) | 0.0705 (5) | |
O7 | 0.1604 (2) | −0.0161 (2) | 0.54961 (7) | 0.0738 (5) | |
H7A | 0.165 (3) | 0.0858 (17) | 0.5317 (9) | 0.081 (5)* | |
H7B | 0.174 (3) | −0.102 (2) | 0.5251 (8) | 0.079 (5)* | |
C8 | −0.00521 (19) | 0.4146 (3) | 0.38708 (8) | 0.0382 (4) | |
H8 | 0.0140 | 0.3229 | 0.4160 | 0.046* | |
C9 | −0.09708 (18) | 0.3720 (2) | 0.33890 (8) | 0.0361 (4) | |
C10 | −0.1206 (2) | 0.5150 (3) | 0.29727 (8) | 0.0415 (4) | |
H10 | −0.1807 | 0.4919 | 0.2640 | 0.050* | |
C11 | −0.0566 (2) | 0.6896 (3) | 0.30467 (9) | 0.0456 (5) | |
H11 | −0.0740 | 0.7846 | 0.2767 | 0.055* | |
C12 | 0.0329 (2) | 0.7240 (3) | 0.35310 (9) | 0.0475 (5) | |
H12 | 0.0771 | 0.8420 | 0.3585 | 0.057* | |
N3 | 0.05566 (17) | 0.5854 (2) | 0.39239 (7) | 0.0417 (4) | |
H3 | 0.114 (2) | 0.611 (3) | 0.4234 (7) | 0.060 (6)* | |
N4 | −0.15849 (18) | 0.1961 (2) | 0.33348 (7) | 0.0526 (5) | |
H4A | −0.1402 | 0.1110 | 0.3601 | 0.063* | |
H4B | −0.2155 | 0.1701 | 0.3035 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0364 (9) | 0.0323 (9) | 0.0310 (9) | 0.0002 (7) | 0.0005 (7) | −0.0019 (7) |
C2 | 0.0363 (9) | 0.0357 (9) | 0.0345 (9) | −0.0023 (7) | −0.0010 (7) | −0.0011 (8) |
C3 | 0.0399 (9) | 0.0378 (9) | 0.0321 (9) | 0.0040 (8) | −0.0020 (7) | 0.0001 (8) |
C4 | 0.0368 (9) | 0.0442 (10) | 0.0358 (10) | 0.0041 (8) | −0.0074 (8) | −0.0103 (8) |
C5 | 0.0364 (9) | 0.0337 (9) | 0.0414 (10) | −0.0021 (7) | 0.0001 (8) | −0.0091 (8) |
C6 | 0.0416 (10) | 0.0328 (9) | 0.0362 (10) | 0.0012 (7) | 0.0020 (8) | −0.0016 (8) |
C7 | 0.0401 (9) | 0.0342 (9) | 0.0303 (9) | −0.0022 (8) | −0.0027 (7) | −0.0007 (7) |
N1 | 0.0528 (10) | 0.0477 (10) | 0.0401 (9) | 0.0066 (8) | −0.0099 (8) | 0.0034 (8) |
N2 | 0.0517 (10) | 0.0409 (10) | 0.0597 (11) | −0.0054 (8) | −0.0030 (8) | −0.0135 (9) |
O1 | 0.0694 (9) | 0.0347 (7) | 0.0456 (8) | −0.0054 (6) | −0.0234 (6) | 0.0066 (6) |
O2 | 0.0595 (8) | 0.0364 (7) | 0.0481 (8) | −0.0112 (6) | −0.0187 (6) | 0.0030 (6) |
O3 | 0.0768 (11) | 0.0651 (10) | 0.0682 (11) | −0.0215 (9) | −0.0165 (8) | 0.0279 (8) |
O4 | 0.0827 (11) | 0.0648 (10) | 0.0606 (10) | 0.0067 (8) | −0.0370 (8) | 0.0070 (8) |
O5 | 0.0684 (10) | 0.0626 (10) | 0.0878 (13) | −0.0155 (8) | −0.0312 (9) | −0.0163 (9) |
O6 | 0.0879 (12) | 0.0435 (9) | 0.0802 (12) | −0.0195 (8) | −0.0087 (9) | 0.0015 (8) |
O7 | 0.1287 (15) | 0.0409 (9) | 0.0519 (10) | −0.0040 (10) | −0.0016 (10) | 0.0062 (7) |
C8 | 0.0405 (10) | 0.0402 (10) | 0.0340 (10) | 0.0025 (8) | −0.0032 (8) | 0.0027 (8) |
C9 | 0.0355 (9) | 0.0399 (10) | 0.0331 (9) | 0.0003 (8) | −0.0011 (7) | −0.0012 (8) |
C10 | 0.0407 (10) | 0.0510 (11) | 0.0327 (10) | 0.0004 (8) | −0.0062 (8) | 0.0009 (8) |
C11 | 0.0499 (11) | 0.0442 (11) | 0.0428 (11) | −0.0006 (9) | −0.0036 (9) | 0.0109 (9) |
C12 | 0.0504 (11) | 0.0415 (11) | 0.0508 (12) | −0.0069 (9) | −0.0012 (9) | 0.0013 (9) |
N3 | 0.0418 (9) | 0.0454 (9) | 0.0379 (9) | −0.0029 (7) | −0.0077 (7) | −0.0034 (7) |
N4 | 0.0662 (11) | 0.0430 (9) | 0.0487 (10) | −0.0114 (8) | −0.0167 (8) | 0.0024 (8) |
C1—C2 | 1.381 (2) | N2—O5 | 1.222 (2) |
C1—C6 | 1.390 (2) | O7—H7A | 0.825 (10) |
C1—C7 | 1.514 (2) | O7—H7B | 0.827 (9) |
C2—C3 | 1.375 (2) | C8—N3 | 1.329 (2) |
C2—H2 | 0.9300 | C8—C9 | 1.385 (2) |
C3—C4 | 1.376 (2) | C8—H8 | 0.9300 |
C3—N1 | 1.468 (2) | C9—N4 | 1.364 (2) |
C4—C5 | 1.368 (3) | C9—C10 | 1.389 (2) |
C4—H4 | 0.9300 | C10—C11 | 1.370 (3) |
C5—C6 | 1.378 (2) | C10—H10 | 0.9300 |
C5—N2 | 1.470 (2) | C11—C12 | 1.365 (3) |
C6—H6 | 0.9300 | C11—H11 | 0.9300 |
C7—O2 | 1.2304 (19) | C12—N3 | 1.330 (2) |
C7—O1 | 1.258 (2) | C12—H12 | 0.9300 |
N1—O3 | 1.214 (2) | N3—H3 | 0.883 (10) |
N1—O4 | 1.2157 (19) | N4—H4A | 0.8600 |
N2—O6 | 1.214 (2) | N4—H4B | 0.8600 |
C2—C1—C6 | 119.60 (16) | O6—N2—C5 | 118.76 (17) |
C2—C1—C7 | 119.93 (15) | O5—N2—C5 | 117.47 (18) |
C6—C1—C7 | 120.47 (15) | H7A—O7—H7B | 108.3 (15) |
C3—C2—C1 | 119.12 (16) | N3—C8—C9 | 120.51 (17) |
C3—C2—H2 | 120.4 | N3—C8—H8 | 119.7 |
C1—C2—H2 | 120.4 | C9—C8—H8 | 119.7 |
C2—C3—C4 | 122.62 (17) | N4—C9—C8 | 120.26 (16) |
C2—C3—N1 | 118.96 (16) | N4—C9—C10 | 122.92 (16) |
C4—C3—N1 | 118.41 (16) | C8—C9—C10 | 116.81 (16) |
C5—C4—C3 | 117.00 (16) | C11—C10—C9 | 120.80 (17) |
C5—C4—H4 | 121.5 | C11—C10—H10 | 119.6 |
C3—C4—H4 | 121.5 | C9—C10—H10 | 119.6 |
C4—C5—C6 | 122.68 (16) | C12—C11—C10 | 119.96 (18) |
C4—C5—N2 | 118.40 (16) | C12—C11—H11 | 120.0 |
C6—C5—N2 | 118.91 (17) | C10—C11—H11 | 120.0 |
C5—C6—C1 | 118.93 (16) | N3—C12—C11 | 118.68 (18) |
C5—C6—H6 | 120.5 | N3—C12—H12 | 120.7 |
C1—C6—H6 | 120.5 | C11—C12—H12 | 120.7 |
O2—C7—O1 | 125.55 (16) | C8—N3—C12 | 123.24 (17) |
O2—C7—C1 | 118.68 (15) | C8—N3—H3 | 119.5 (14) |
O1—C7—C1 | 115.77 (15) | C12—N3—H3 | 117.3 (14) |
O3—N1—O4 | 123.39 (17) | C9—N4—H4A | 120.0 |
O3—N1—C3 | 118.54 (15) | C9—N4—H4B | 120.0 |
O4—N1—C3 | 118.07 (17) | H4A—N4—H4B | 120.0 |
O6—N2—O5 | 123.77 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O2 | 0.83 (1) | 1.99 (1) | 2.805 (2) | 170 (2) |
O7—H7B···O1i | 0.83 (1) | 2.08 (1) | 2.883 (2) | 165 (2) |
N3—H3···O1 | 0.88 (1) | 1.73 (1) | 2.6116 (19) | 176 (2) |
N4—H4A···O7ii | 0.86 | 2.13 | 2.904 (2) | 149 |
N4—H4B···O4iii | 0.86 | 2.45 | 3.223 (2) | 150 |
N4—H4B···O3ii | 0.86 | 2.59 | 3.110 (2) | 120 |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C5H7N2+·C7H3N2O6−·H2O |
Mr | 324.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 8.904 (2), 7.0683 (16), 22.331 (5) |
β (°) | 90.002 (3) |
V (Å3) | 1405.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.40 × 0.11 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.950, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7329, 2743, 2110 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.116, 1.04 |
No. of reflections | 2743 |
No. of parameters | 220 |
No. of restraints | 16 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.18 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O2 | 0.825 (10) | 1.990 (10) | 2.805 (2) | 170 (2) |
O7—H7B···O1i | 0.827 (9) | 2.075 (10) | 2.883 (2) | 165 (2) |
N3—H3···O1 | 0.883 (10) | 1.730 (10) | 2.6116 (19) | 176 (2) |
N4—H4A···O7ii | 0.86 | 2.13 | 2.904 (2) | 148.9 |
N4—H4B···O4iii | 0.86 | 2.45 | 3.223 (2) | 150.4 |
N4—H4B···O3ii | 0.86 | 2.59 | 3.110 (2) | 120.3 |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) x−1, −y+1/2, z−1/2. |
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This work continues our previous synthetic and structural studies of supramolecular salts (Wang & Wei, 2007). Herein we present the crystal structure of the title salt, (I).
The title salt contains one 3-aminopyridinium cation, one 3,5-dinitrobenzoate anion and one crystallization water molecule. These components are connected by N—H···O and O—H···O hydrogen bonds, in which the water oxygen atom, two nitrogen atoms of 3-aminopyridinium cation act as the hydrogen-bond acceptor and 3-aminopyridinium cation acts as the hydrogen-bond donor (Table 1). This results in an infinite two-dimensional network runing parallel to the plane (102) (Fig. 2).