organic compounds
The crystal structure of the title compound, C5H6NO+·C10H9O6-, consists of pairs of 3-hydroxypyridinium cations and pairs of 3-(carboxymethoxy)phenoxyacetate anions that are connected via hydrogen bonding into linear ribbons, which are approximately planar. The asymmetric unit consists of one cation and one anion, each located in a general position.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023219/nc6000sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023219/nc6000Isup2.hkl |
CCDC reference: 253025
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.057
- wR factor = 0.129
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.790 0.978 Tmin' and Tmax expected: 0.956 0.978 RR' = 0.827 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.23 PLAT731_ALERT_1_C Bond Calc 0.87(3), Rep 0.870(10) ...... 3.00 su-Rat N1 -H1N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.87(3), Rep 0.870(10) ...... 3.00 su-Rat N1 -H1N 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.77(3), Rep 1.770(10) ...... 3.00 su-Rat H1N -O2 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
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.
3-Hydroxypyridinium 3-(carboxymethoxy)phenoxyacetate top
Crystal data top
C5H6NO+·C10H9O6− | F(000) = 672 |
Mr = 321.28 | Dx = 1.453 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6106 reflections |
a = 15.960 (2) Å | θ = 4.4–27.5° |
b = 4.8404 (4) Å | µ = 0.12 mm−1 |
c = 20.313 (3) Å | T = 295 K |
β = 110.58 (4)° | Prism, colorless |
V = 1469.1 (3) Å3 | 0.38 × 0.25 × 0.19 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3367 independent reflections |
Radiation source: fine-focus sealed tube | 2121 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.790, Tmax = 0.978 | k = −6→5 |
13092 measured reflections | l = −26→26 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.1723P] where P = (Fo2 + 2Fc2)/3 |
3367 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.20 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.5662 (1) | 0.2796 (4) | 0.3703 (1) | 0.0528 (5) | |
O2 | 0.2829 (1) | 0.4081 (3) | 0.4844 (1) | 0.0463 (4) | |
O3 | 0.3853 (1) | 0.0884 (3) | 0.5325 (1) | 0.0489 (5) | |
O4 | 0.2085 (1) | 0.3617 (3) | 0.5784 (1) | 0.0457 (4) | |
O5 | −0.0262 (1) | 0.7256 (3) | 0.6457 (1) | 0.0354 (4) | |
O6 | −0.1579 (1) | 1.0966 (4) | 0.6316 (1) | 0.0557 (5) | |
O7 | −0.1488 (1) | 1.2422 (3) | 0.5298 (1) | 0.0445 (4) | |
N1 | 0.3641 (1) | 0.4975 (5) | 0.3935 (1) | 0.0493 (5) | |
C1 | 0.4409 (2) | 0.3651 (5) | 0.4055 (1) | 0.0420 (6) | |
C2 | 0.4875 (1) | 0.4008 (5) | 0.3603 (1) | 0.0372 (5) | |
C3 | 0.4512 (2) | 0.5730 (5) | 0.3028 (1) | 0.0452 (6) | |
C4 | 0.3716 (2) | 0.7053 (6) | 0.2926 (1) | 0.0584 (7) | |
C5 | 0.3283 (2) | 0.6671 (6) | 0.3393 (2) | 0.0591 (8) | |
C6 | 0.3192 (1) | 0.2306 (5) | 0.5308 (1) | 0.0352 (5) | |
C7 | 0.2821 (1) | 0.1822 (5) | 0.5889 (1) | 0.0347 (5) | |
C8 | 0.1643 (1) | 0.3542 (4) | 0.6254 (1) | 0.0302 (5) | |
C9 | 0.0929 (1) | 0.5379 (4) | 0.6099 (1) | 0.0308 (5) | |
C10 | 0.0447 (1) | 0.5515 (4) | 0.6547 (1) | 0.0278 (4) | |
C11 | 0.0670 (1) | 0.3836 (4) | 0.7136 (1) | 0.0324 (5) | |
C12 | 0.1367 (1) | 0.2012 (4) | 0.7271 (1) | 0.0340 (5) | |
C13 | 0.1869 (1) | 0.1830 (4) | 0.6835 (1) | 0.0328 (5) | |
C14 | −0.0514 (1) | 0.8971 (4) | 0.5857 (1) | 0.0323 (5) | |
C15 | −0.1257 (1) | 1.0870 (5) | 0.5866 (1) | 0.0336 (5) | |
H1o | 0.577 (2) | 0.156 (5) | 0.402 (1) | 0.09 (1)* | |
H7o | −0.191 (1) | 1.348 (5) | 0.530 (2) | 0.09 (1)* | |
H1n | 0.334 (2) | 0.466 (6) | 0.421 (1) | 0.07 (1)* | |
H1 | 0.4632 | 0.2488 | 0.4443 | 0.050* | |
H3 | 0.4807 | 0.5989 | 0.2711 | 0.054* | |
H4 | 0.3472 | 0.8209 | 0.2540 | 0.070* | |
H5 | 0.2747 | 0.7581 | 0.3332 | 0.071* | |
H7a | 0.2630 | −0.0084 | 0.5882 | 0.042* | |
H7b | 0.3280 | 0.2184 | 0.6343 | 0.042* | |
H9 | 0.0779 | 0.6497 | 0.5702 | 0.037* | |
H11 | 0.0348 | 0.3945 | 0.7437 | 0.039* | |
H12 | 0.1508 | 0.0871 | 0.7664 | 0.041* | |
H13 | 0.2343 | 0.0594 | 0.6931 | 0.039* | |
H14a | −0.0714 | 0.7845 | 0.5435 | 0.039* | |
H14b | −0.0004 | 1.0051 | 0.5854 | 0.039* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.052 (1) | 0.068 (1) | 0.049 (1) | 0.025 (1) | 0.031 (1) | 0.018 (1) |
O2 | 0.048 (1) | 0.056 (1) | 0.044 (1) | 0.023 (1) | 0.028 (1) | 0.020 (1) |
O3 | 0.047 (1) | 0.060 (1) | 0.050 (1) | 0.025 (1) | 0.030 (1) | 0.017 (1) |
O4 | 0.046 (1) | 0.058 (1) | 0.045 (1) | 0.027 (1) | 0.031 (1) | 0.022 (1) |
O5 | 0.040 (1) | 0.038 (1) | 0.036 (1) | 0.012 (1) | 0.022 (1) | 0.008 (1) |
O6 | 0.054 (1) | 0.072 (1) | 0.053 (1) | 0.027 (1) | 0.034 (1) | 0.014 (1) |
O7 | 0.048 (1) | 0.048 (1) | 0.042 (1) | 0.021 (1) | 0.023 (1) | 0.013 (1) |
N1 | 0.049 (1) | 0.063 (1) | 0.047 (1) | 0.007 (1) | 0.032 (1) | 0.001 (1) |
C1 | 0.047 (1) | 0.050 (1) | 0.034 (1) | 0.007 (1) | 0.021 (1) | 0.004 (1) |
C2 | 0.041 (1) | 0.042 (1) | 0.034 (1) | 0.006 (1) | 0.018 (1) | 0.002 (1) |
C3 | 0.050 (1) | 0.056 (2) | 0.037 (1) | 0.011 (1) | 0.025 (1) | 0.010 (1) |
C4 | 0.059 (2) | 0.070 (2) | 0.050 (2) | 0.023 (2) | 0.023 (1) | 0.020 (1) |
C5 | 0.049 (1) | 0.074 (2) | 0.061 (2) | 0.026 (2) | 0.027 (1) | 0.013 (2) |
C6 | 0.034 (1) | 0.041 (1) | 0.034 (1) | 0.008 (1) | 0.016 (1) | 0.004 (1) |
C7 | 0.032 (1) | 0.041 (1) | 0.035 (1) | 0.010 (1) | 0.015 (1) | 0.005 (1) |
C8 | 0.030 (1) | 0.033 (1) | 0.031 (1) | 0.002 (1) | 0.015 (1) | 0.001 (1) |
C9 | 0.033 (1) | 0.032 (1) | 0.029 (1) | 0.006 (1) | 0.014 (1) | 0.007 (1) |
C10 | 0.030 (1) | 0.027 (1) | 0.029 (1) | 0.001 (1) | 0.012 (1) | −0.002 (1) |
C11 | 0.037 (1) | 0.036 (1) | 0.030 (1) | 0.001 (1) | 0.018 (1) | 0.002 (1) |
C12 | 0.038 (1) | 0.035 (1) | 0.029 (1) | 0.002 (1) | 0.011 (1) | 0.008 (1) |
C13 | 0.031 (1) | 0.032 (1) | 0.035 (1) | 0.005 (1) | 0.011 (1) | 0.005 (1) |
C14 | 0.035 (1) | 0.034 (1) | 0.031 (1) | 0.006 (1) | 0.015 (1) | 0.004 (1) |
C15 | 0.032 (1) | 0.036 (1) | 0.035 (1) | 0.003 (1) | 0.013 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
O1—C2 | 1.334 (3) | C10—C11 | 1.385 (3) |
O2—C6 | 1.257 (3) | C11—C12 | 1.370 (3) |
O3—C6 | 1.250 (2) | C12—C13 | 1.391 (3) |
O4—C8 | 1.374 (2) | C14—C15 | 1.506 (3) |
O4—C7 | 1.416 (2) | O1—H1o | 0.86 (1) |
O5—C10 | 1.371 (2) | O7—H7o | 0.85 (1) |
O5—C14 | 1.410 (2) | N1—H1n | 0.87 (1) |
O6—C15 | 1.196 (2) | C1—H1 | 0.93 |
O7—C15 | 1.318 (3) | C3—H3 | 0.93 |
N1—C1 | 1.327 (3) | C4—H4 | 0.93 |
N1—C5 | 1.331 (3) | C5—H5 | 0.93 |
C1—C2 | 1.383 (3) | C7—H7a | 0.97 |
C2—C3 | 1.385 (3) | C7—H7b | 0.97 |
C3—C4 | 1.372 (3) | C9—H9 | 0.93 |
C4—C5 | 1.369 (4) | C11—H11 | 0.93 |
C6—C7 | 1.514 (3) | C12—H12 | 0.93 |
C8—C9 | 1.391 (3) | C13—H13 | 0.93 |
C8—C13 | 1.382 (3) | C14—H14a | 0.97 |
C9—C10 | 1.384 (3) | C14—H14b | 0.97 |
C7—O4—C8 | 118.7 (2) | C15—O7—H7o | 108 (2) |
C10—O5—C14 | 116.7 (2) | C1—N1—H1n | 119 (2) |
C1—N1—C5 | 123.4 (2) | C5—N1—H1n | 117 (2) |
N1—C1—C2 | 119.7 (2) | N1—C1—H1 | 120.2 |
O1—C2—C1 | 122.7 (2) | C2—C1—H1 | 120.2 |
O1—C2—C3 | 119.1 (2) | C4—C3—H3 | 120.0 |
C1—C2—C3 | 118.2 (2) | C2—C3—H3 | 120.0 |
C2—C3—C4 | 120.0 (2) | C5—C4—H4 | 120.0 |
C3—C4—C5 | 120.0 (2) | C3—C4—H4 | 120.0 |
N1—C5—C4 | 118.8 (2) | N1—C5—H5 | 120.6 |
O3—C6—O2 | 124.0 (2) | C4—C5—H5 | 120.6 |
O3—C6—C7 | 116.8 (2) | O4—C7—H7a | 110.0 |
O2—C6—C7 | 119.2 (2) | C6—C7—H7a | 110.0 |
O4—C7—C6 | 108.5 (2) | O4—C7—H7b | 110.0 |
O4—C8—C13 | 124.4 (2) | C6—C7—H7b | 110.0 |
O4—C8—C9 | 114.0 (2) | H7a—C7—H7b | 108.4 |
C9—C8—C13 | 121.6 (2) | C10—C9—H9 | 120.6 |
C8—C9—C10 | 118.8 (2) | C8—C9—H9 | 120.6 |
O5—C10—C9 | 124.4 (2) | C12—C11—H11 | 120.1 |
O5—C10—C11 | 115.2 (2) | C10—C11—H11 | 120.1 |
C9—C10—C11 | 120.4 (2) | C11—C12—H12 | 119.3 |
C10—C11—C12 | 119.7 (2) | C13—C12—H12 | 119.3 |
C11—C12—C13 | 121.4 (2) | C8—C13—H13 | 121.0 |
C8—C13—C12 | 118.0 (2) | C12—C13—H13 | 121.0 |
O5—C14—C15 | 109.6 (2) | O5—C14—H14a | 109.8 |
O6—C15—O7 | 125.8 (2) | C15—C14—H14a | 109.7 |
O6—C15—C14 | 125.8 (2) | O5—C14—H14b | 109.7 |
O7—C15—C14 | 108.4 (2) | C15—C14—H14b | 109.8 |
C2—O1—H1o | 111 (2) | H14a—C14—H14b | 108.2 |
C5—N1—C1—C2 | −0.1 (4) | C13—C8—C9—C10 | 1.0 (3) |
N1—C1—C2—O1 | 178.2 (2) | C14—O5—C10—C9 | 1.1 (3) |
N1—C1—C2—C3 | −0.8 (4) | C14—O5—C10—C11 | −179.2 (2) |
O1—C2—C3—C4 | −178.3 (2) | C8—C9—C10—O5 | 179.3 (2) |
C1—C2—C3—C4 | 0.9 (4) | C8—C9—C10—C11 | −0.4 (3) |
C2—C3—C4—C5 | 0.0 (4) | O5—C10—C11—C12 | 179.7 (2) |
C1—N1—C5—C4 | 1.0 (4) | C9—C10—C11—C12 | −0.6 (3) |
C3—C4—C5—N1 | −1.0 (4) | C10—C11—C12—C13 | 0.9 (3) |
C8—O4—C7—C6 | −179.8 (2) | O4—C8—C13—C12 | 179.0 (2) |
O3—C6—C7—O4 | 179.7 (2) | C9—C8—C13—C12 | −0.7 (3) |
O2—C6—C7—O4 | −0.2 (3) | C11—C12—C13—C8 | −0.3 (3) |
C7—O4—C8—C13 | 0.5 (3) | C10—O5—C14—C15 | −176.2 (2) |
C7—O4—C8—C9 | −179.8 (2) | O5—C14—C15—O6 | 1.2 (3) |
O4—C8—C9—C10 | −178.7 (2) | O5—C14—C15—O7 | −179.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O2 | 0.87 (1) | 1.77 (1) | 2.638 (3) | 173 (3) |
O1—H1o···O3i | 0.86 (1) | 1.72 (1) | 2.569 (2) | 172 (3) |
O7—H7o···O2ii | 0.85 (1) | 1.82 (1) | 2.663 (2) | 170 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z+1. |