organic compounds
In the title salt, C5H7N2+·C7H5O4−,anions are linked through O—HO hydrogen bonds into an infinite C22(16) chain parallel to the [010] direction. Adjacent chains are further organized into a three-dimensional supramolecular structure based on N—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009439/bh2086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009439/bh2086Isup2.hkl |
CCDC reference: 642913
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.114
- Data-to-parameter ratio = 12.9
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 . ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C7 H5 O4
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 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.
3-aminopyridinium 2,4-dihydroxybenzoate top
Crystal data top
C5H7N2+·C7H5O4− | F(000) = 520 |
Mr = 248.24 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4131 reflections |
a = 11.7788 (15) Å | θ = 3.0–28.0° |
b = 8.5808 (11) Å | µ = 0.11 mm−1 |
c = 12.3340 (16) Å | T = 296 K |
β = 111.113 (2)° | Block, yellow |
V = 1162.9 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Data collection top
Bruker SMART APEX CCD diffractometer | 2286 independent reflections |
Radiation source: fine-focus sealed tube | 2044 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −14→11 |
Tmin = 0.968, Tmax = 0.979 | k = −10→10 |
8507 measured reflections | l = −15→15 |
Refinement top
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0671P)2 + 0.1693P] where P = (Fo2 + 2Fc2)/3 |
2286 reflections | (Δ/σ)max = 0.001 |
177 parameters | Δρmax = 0.20 e Å−3 |
3 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.93717 (11) | 1.04675 (13) | 1.24661 (10) | 0.0340 (3) | |
C2 | 1.02462 (11) | 1.09169 (16) | 1.35365 (11) | 0.0408 (3) | |
C3 | 0.99288 (13) | 1.18526 (17) | 1.42994 (11) | 0.0472 (3) | |
H3 | 1.0513 | 1.2132 | 1.5010 | 0.057* | |
C4 | 0.87487 (12) | 1.23690 (15) | 1.40050 (10) | 0.0391 (3) | |
C5 | 0.78723 (12) | 1.19841 (14) | 1.29285 (11) | 0.0386 (3) | |
H5A | 0.7081 | 1.2360 | 1.2718 | 0.046* | |
C6 | 0.81927 (11) | 1.10462 (14) | 1.21864 (10) | 0.0368 (3) | |
H6 | 0.7605 | 1.0786 | 1.1472 | 0.044* | |
C7 | 0.96975 (11) | 0.94251 (14) | 1.16599 (11) | 0.0368 (3) | |
C8 | 0.87630 (12) | 0.67694 (14) | 0.84055 (11) | 0.0386 (3) | |
H8 | 0.7985 | 0.7171 | 0.8237 | 0.046* | |
C9 | 0.89967 (12) | 0.57732 (15) | 0.76250 (11) | 0.0383 (3) | |
C10 | 1.01906 (13) | 0.52396 (16) | 0.79214 (12) | 0.0435 (3) | |
H10 | 1.0387 | 0.4584 | 0.7415 | 0.052* | |
C11 | 1.10741 (13) | 0.56677 (16) | 0.89465 (12) | 0.0454 (3) | |
H11 | 1.1866 | 0.5303 | 0.9136 | 0.054* | |
C12 | 1.07871 (13) | 0.66387 (15) | 0.96959 (11) | 0.0436 (3) | |
H12 | 1.1378 | 0.6930 | 1.0399 | 0.052* | |
N1 | 0.96540 (10) | 0.71533 (12) | 0.93997 (9) | 0.0392 (3) | |
N2 | 0.81077 (13) | 0.53484 (18) | 0.66170 (12) | 0.0620 (4) | |
H2A | 0.7370 (9) | 0.5588 (19) | 0.6499 (14) | 0.053 (4)* | |
H1 | 0.9430 (15) | 0.7780 (16) | 0.9841 (13) | 0.056 (4)* | |
H2B | 0.8316 (17) | 0.478 (2) | 0.6148 (14) | 0.074 (6)* | |
O1 | 0.88626 (8) | 0.89919 (11) | 1.07278 (7) | 0.0447 (3) | |
O2 | 1.07829 (9) | 0.89982 (13) | 1.19233 (9) | 0.0537 (3) | |
O3 | 1.14156 (9) | 1.04575 (15) | 1.38534 (9) | 0.0645 (3) | |
H3A | 1.1490 | 0.9879 | 1.3354 | 0.097* | |
O4 | 0.84603 (10) | 1.32595 (13) | 1.47787 (8) | 0.0545 (3) | |
H4 | 0.7726 | 1.3426 | 1.4530 | 0.082* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0353 (6) | 0.0359 (6) | 0.0335 (6) | −0.0019 (5) | 0.0158 (5) | −0.0010 (4) |
C2 | 0.0340 (7) | 0.0480 (7) | 0.0391 (7) | 0.0035 (5) | 0.0114 (5) | −0.0021 (5) |
C3 | 0.0424 (8) | 0.0602 (8) | 0.0332 (6) | 0.0006 (6) | 0.0067 (5) | −0.0093 (6) |
C4 | 0.0454 (7) | 0.0405 (6) | 0.0356 (6) | −0.0003 (5) | 0.0197 (5) | −0.0049 (5) |
C5 | 0.0332 (6) | 0.0421 (6) | 0.0423 (6) | 0.0006 (5) | 0.0159 (5) | −0.0046 (5) |
C6 | 0.0333 (6) | 0.0417 (6) | 0.0351 (6) | −0.0032 (5) | 0.0120 (5) | −0.0057 (5) |
C7 | 0.0381 (7) | 0.0389 (6) | 0.0384 (6) | −0.0007 (5) | 0.0197 (5) | −0.0003 (5) |
C8 | 0.0368 (7) | 0.0406 (6) | 0.0422 (7) | −0.0002 (5) | 0.0187 (6) | −0.0039 (5) |
C9 | 0.0380 (7) | 0.0418 (6) | 0.0361 (6) | −0.0043 (5) | 0.0145 (5) | −0.0053 (5) |
C10 | 0.0453 (7) | 0.0452 (7) | 0.0452 (7) | 0.0025 (5) | 0.0223 (6) | −0.0088 (6) |
C11 | 0.0366 (7) | 0.0482 (7) | 0.0501 (7) | 0.0036 (5) | 0.0141 (6) | −0.0001 (6) |
C12 | 0.0453 (8) | 0.0462 (7) | 0.0356 (6) | −0.0064 (6) | 0.0101 (6) | −0.0020 (5) |
N1 | 0.0493 (6) | 0.0380 (6) | 0.0355 (5) | −0.0045 (5) | 0.0215 (5) | −0.0063 (4) |
N2 | 0.0422 (7) | 0.0864 (10) | 0.0516 (8) | −0.0013 (7) | 0.0099 (6) | −0.0303 (7) |
O1 | 0.0434 (5) | 0.0553 (6) | 0.0389 (5) | −0.0018 (4) | 0.0190 (4) | −0.0133 (4) |
O2 | 0.0400 (5) | 0.0681 (7) | 0.0557 (6) | 0.0087 (4) | 0.0205 (5) | −0.0128 (5) |
O3 | 0.0365 (6) | 0.0906 (9) | 0.0557 (6) | 0.0151 (5) | 0.0039 (5) | −0.0207 (6) |
O4 | 0.0542 (6) | 0.0675 (7) | 0.0423 (5) | 0.0095 (5) | 0.0180 (5) | −0.0173 (5) |
Geometric parameters (Å, º) top
C1—C6 | 1.3961 (17) | C8—C9 | 1.3872 (17) |
C1—C2 | 1.4047 (17) | C8—H8 | 0.9300 |
C1—C7 | 1.4869 (16) | C9—N2 | 1.3554 (18) |
C2—O3 | 1.3482 (16) | C9—C10 | 1.3966 (19) |
C2—C3 | 1.3868 (18) | C10—C11 | 1.3669 (19) |
C3—C4 | 1.3772 (19) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.3741 (19) |
C4—O4 | 1.3577 (15) | C11—H11 | 0.9300 |
C4—C5 | 1.3965 (18) | C12—N1 | 1.3262 (18) |
C5—C6 | 1.3699 (17) | C12—H12 | 0.9300 |
C5—H5A | 0.9300 | N1—H1 | 0.871 (9) |
C6—H6 | 0.9300 | N2—H2A | 0.853 (9) |
C7—O2 | 1.2551 (16) | N2—H2B | 0.858 (9) |
C7—O1 | 1.2699 (15) | O3—H3A | 0.8200 |
C8—N1 | 1.3366 (17) | O4—H4 | 0.8200 |
C6—C1—C2 | 117.52 (11) | N1—C8—H8 | 119.9 |
C6—C1—C7 | 121.47 (11) | C9—C8—H8 | 119.9 |
C2—C1—C7 | 121.01 (11) | N2—C9—C8 | 121.43 (13) |
O3—C2—C3 | 118.01 (12) | N2—C9—C10 | 121.62 (12) |
O3—C2—C1 | 121.26 (12) | C8—C9—C10 | 116.95 (12) |
C3—C2—C1 | 120.73 (12) | C11—C10—C9 | 120.89 (12) |
C4—C3—C2 | 120.04 (12) | C11—C10—H10 | 119.6 |
C4—C3—H3 | 120.0 | C9—C10—H10 | 119.6 |
C2—C3—H3 | 120.0 | C10—C11—C12 | 119.69 (13) |
O4—C4—C3 | 118.69 (11) | C10—C11—H11 | 120.2 |
O4—C4—C5 | 121.00 (12) | C12—C11—H11 | 120.2 |
C3—C4—C5 | 120.31 (11) | N1—C12—C11 | 118.93 (12) |
C6—C5—C4 | 119.15 (12) | N1—C12—H12 | 120.5 |
C6—C5—H5A | 120.4 | C11—C12—H12 | 120.5 |
C4—C5—H5A | 120.4 | C12—N1—C8 | 123.39 (11) |
C5—C6—C1 | 122.19 (11) | C12—N1—H1 | 122.3 (12) |
C5—C6—H6 | 118.9 | C8—N1—H1 | 114.3 (12) |
C1—C6—H6 | 118.9 | C9—N2—H2A | 119.6 (11) |
O2—C7—O1 | 122.24 (11) | C9—N2—H2B | 117.2 (13) |
O2—C7—C1 | 119.13 (11) | H2A—N2—H2B | 122.9 (18) |
O1—C7—C1 | 118.64 (11) | C2—O3—H3A | 109.5 |
N1—C8—C9 | 120.14 (12) | C4—O4—H4 | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O1i | 0.82 | 1.85 | 2.6533 (14) | 168 |
N1—H1···O1 | 0.87 (1) | 1.80 (1) | 2.6723 (13) | 176 (2) |
O3—H3A···O2 | 0.82 | 1.82 | 2.5520 (14) | 148 |
N2—H2B···O4ii | 0.86 (1) | 2.19 (1) | 3.0339 (16) | 169 (2) |
N2—H2A···O2iii | 0.85 (1) | 2.14 (1) | 2.9497 (18) | 157 (2) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+5/2; (ii) x, y−1, z−1; (iii) x−1/2, −y+3/2, z−1/2. |