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The title compound, C6H9N2+·C8H5O3·H2O, contains hydrogen-bonded [R22(8)R42(8)R22(8)] motifs involving 2-amino-6-methyl­pyridinium and 2-carbonyl­benzoate ions. These motifs are connected by three O—H...O hydrogen bonds involving two water O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021106/kp2025sup1.cif
Contains datablocks I, orhanm19

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021106/kp2025Isup2.hkl
Contains datablock I

CCDC reference: 613757

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.117
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.71 mm
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-amino-6-methylpyridinium 2-formylbenzoate monohydrate top
Crystal data top
C6H9N2+·C8H5O3·H2OF(000) = 1168
Mr = 276.29Dx = 1.341 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 14925 reflections
a = 34.171 (3) Åθ = 1.4–25.1°
b = 4.9220 (3) ŵ = 0.10 mm1
c = 19.4423 (17) ÅT = 296 K
β = 123.172 (6)°Prism, colourless
V = 2737.1 (4) Å30.71 × 0.38 × 0.12 mm
Z = 8
Data collection top
STOE IPDS 2
diffractometer
2400 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1794 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 6.67 pixels mm-1θmax = 25.1°, θmin = 1.4°
ω scanh = 4040
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 55
Tmin = 0.949, Tmax = 0.991l = 2222
14999 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.2766P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2400 reflectionsΔρmax = 0.23 e Å3
199 parametersΔρmin = 0.18 e Å3
2 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0055 (9)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.37513 (6)0.4018 (3)0.48108 (10)0.0464 (4)
C20.42262 (6)0.4310 (3)0.50971 (10)0.0498 (4)
C30.44175 (7)0.2674 (4)0.47689 (12)0.0612 (5)
H30.47300.28800.49500.073*
C40.41502 (8)0.0762 (4)0.41807 (13)0.0667 (5)
H40.42820.03150.39660.080*
C50.36879 (8)0.0439 (4)0.39092 (12)0.0635 (5)
H50.35080.08760.35170.076*
C60.34902 (7)0.2059 (4)0.42172 (11)0.0545 (4)
H60.31760.18390.40240.065*
C70.35212 (6)0.5721 (3)0.51371 (10)0.0481 (4)
C80.45341 (7)0.6404 (4)0.56985 (12)0.0618 (5)
H80.43970.79110.57730.074*
C90.31534 (6)0.1379 (3)0.62118 (11)0.0486 (4)
C100.30461 (7)0.3376 (4)0.65971 (12)0.0566 (5)
H100.27370.37490.64140.068*
C110.34020 (7)0.4759 (4)0.72435 (12)0.0611 (5)
H110.33340.60950.75010.073*
C120.38653 (7)0.4212 (4)0.75258 (11)0.0593 (5)
H120.41050.51720.79690.071*
C130.39655 (6)0.2262 (4)0.71487 (10)0.0525 (4)
C140.44424 (7)0.1488 (5)0.73689 (14)0.0734 (6)
H14A0.44740.19130.69200.088*
H14B0.44880.04250.74810.088*
H14C0.46720.24790.78480.088*
N10.36046 (5)0.0876 (3)0.65069 (9)0.0481 (4)
H10.36700.03870.62790.058*
N20.28339 (6)0.0062 (3)0.55626 (11)0.0608 (4)
O10.30863 (4)0.6029 (3)0.46957 (8)0.0632 (4)
O20.37815 (5)0.6702 (3)0.58409 (8)0.0633 (4)
O30.49526 (6)0.6246 (4)0.60939 (11)0.0975 (6)
O40.25579 (6)0.6896 (3)0.29248 (10)0.0760 (5)
H2A0.2549 (9)0.001 (5)0.5438 (14)0.075 (7)*
H2B0.2940 (8)0.131 (5)0.5346 (14)0.078 (7)*
H4A0.2722 (8)0.651 (5)0.3414 (11)0.089 (8)*
H4B0.2520 (10)0.545 (4)0.2674 (17)0.104 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0503 (9)0.0436 (8)0.0459 (9)0.0031 (7)0.0266 (8)0.0070 (7)
C20.0509 (10)0.0494 (9)0.0489 (9)0.0031 (7)0.0272 (8)0.0071 (7)
C30.0596 (11)0.0641 (11)0.0680 (11)0.0090 (9)0.0401 (10)0.0085 (10)
C40.0844 (15)0.0603 (11)0.0667 (12)0.0145 (11)0.0486 (12)0.0028 (9)
C50.0778 (14)0.0516 (10)0.0561 (11)0.0039 (9)0.0334 (10)0.0031 (8)
C60.0551 (10)0.0493 (9)0.0536 (10)0.0016 (8)0.0261 (9)0.0009 (8)
C70.0493 (10)0.0473 (9)0.0509 (10)0.0006 (7)0.0294 (9)0.0033 (7)
C80.0578 (12)0.0663 (12)0.0601 (11)0.0063 (9)0.0315 (10)0.0001 (9)
C90.0461 (9)0.0459 (9)0.0529 (9)0.0009 (7)0.0265 (8)0.0022 (7)
C100.0553 (11)0.0551 (10)0.0654 (11)0.0038 (8)0.0368 (10)0.0006 (9)
C110.0748 (13)0.0559 (10)0.0619 (11)0.0004 (9)0.0434 (11)0.0052 (9)
C120.0640 (12)0.0582 (11)0.0500 (10)0.0074 (9)0.0275 (9)0.0063 (8)
C130.0483 (10)0.0557 (10)0.0472 (9)0.0052 (8)0.0223 (8)0.0020 (8)
C140.0466 (11)0.0877 (15)0.0712 (13)0.0038 (10)0.0227 (10)0.0092 (11)
N10.0441 (8)0.0483 (8)0.0508 (8)0.0005 (6)0.0253 (7)0.0022 (6)
N20.0430 (9)0.0605 (10)0.0724 (11)0.0044 (7)0.0275 (8)0.0156 (8)
O10.0489 (8)0.0750 (9)0.0668 (8)0.0026 (6)0.0325 (7)0.0054 (6)
O20.0636 (8)0.0696 (8)0.0538 (7)0.0080 (6)0.0303 (7)0.0068 (6)
O30.0549 (10)0.1075 (14)0.0928 (12)0.0070 (8)0.0165 (9)0.0067 (10)
O40.0941 (12)0.0596 (9)0.0636 (9)0.0079 (8)0.0363 (9)0.0053 (8)
Geometric parameters (Å, º) top
C1—C61.389 (2)C9—C101.401 (3)
C1—C21.405 (2)C10—C111.360 (3)
C1—C71.506 (2)C10—H100.9300
C2—C31.393 (3)C11—C121.389 (3)
C2—C81.480 (3)C11—H110.9300
C3—C41.373 (3)C12—C131.361 (3)
C3—H30.9300C12—H120.9300
C4—C51.374 (3)C13—N11.364 (2)
C4—H40.9300C13—C141.490 (3)
C5—C61.376 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—O21.251 (2)N1—H10.8600
C7—O11.254 (2)N2—H2A0.87 (2)
C8—O31.200 (2)N2—H2B0.92 (3)
C8—H80.9300O4—H4A0.820 (17)
C9—N21.334 (2)O4—H4B0.834 (17)
C9—N11.341 (2)
C6—C1—C2118.52 (16)N1—C9—C10118.46 (16)
C6—C1—C7119.35 (15)C11—C10—C9118.83 (17)
C2—C1—C7122.13 (15)C11—C10—H10120.6
C3—C2—C1119.29 (17)C9—C10—H10120.6
C3—C2—C8117.09 (17)C10—C11—C12121.17 (17)
C1—C2—C8123.50 (16)C10—C11—H11119.4
C4—C3—C2120.85 (19)C12—C11—H11119.4
C4—C3—H3119.6C13—C12—C11119.49 (17)
C2—C3—H3119.6C13—C12—H12120.3
C3—C4—C5120.04 (18)C11—C12—H12120.3
C3—C4—H4120.0C12—C13—N1118.53 (17)
C5—C4—H4120.0C12—C13—C14125.70 (17)
C4—C5—C6120.05 (19)N1—C13—C14115.77 (17)
C4—C5—H5120.0C13—C14—H14A109.5
C6—C5—H5120.0C13—C14—H14B109.5
C5—C6—C1121.24 (18)H14A—C14—H14B109.5
C5—C6—H6119.4C13—C14—H14C109.5
C1—C6—H6119.4H14A—C14—H14C109.5
O2—C7—O1124.67 (16)H14B—C14—H14C109.5
O2—C7—C1116.94 (15)C9—N1—C13123.49 (15)
O1—C7—C1118.38 (15)C9—N1—H1118.3
O3—C8—C2123.0 (2)C13—N1—H1118.3
O3—C8—H8118.5C9—N2—H2A117.5 (15)
C2—C8—H8118.5C9—N2—H2B117.5 (14)
N2—C9—N1117.44 (16)H2A—N2—H2B124 (2)
N2—C9—C10124.11 (17)H4A—O4—H4B106 (3)
C6—C1—C2—C31.2 (2)C2—C1—C7—O1156.85 (16)
C7—C1—C2—C3179.90 (15)C3—C2—C8—O323.4 (3)
C6—C1—C2—C8177.07 (16)C1—C2—C8—O3160.6 (2)
C7—C1—C2—C84.0 (2)N2—C9—C10—C11178.46 (18)
C1—C2—C3—C41.0 (3)N1—C9—C10—C111.2 (3)
C8—C2—C3—C4177.14 (18)C9—C10—C11—C120.3 (3)
C2—C3—C4—C50.1 (3)C10—C11—C12—C130.1 (3)
C3—C4—C5—C61.0 (3)C11—C12—C13—N10.8 (3)
C4—C5—C6—C10.8 (3)C11—C12—C13—C14178.67 (19)
C2—C1—C6—C50.3 (3)N2—C9—N1—C13177.73 (16)
C7—C1—C6—C5179.26 (16)C10—C9—N1—C132.0 (3)
C6—C1—C7—O2154.87 (16)C12—C13—N1—C91.7 (3)
C2—C1—C7—O224.0 (2)C14—C13—N1—C9177.74 (17)
C6—C1—C7—O124.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.87 (2)2.10 (2)2.939 (2)163 (2)
N2—H2B···O1ii0.92 (3)2.06 (3)2.980 (2)171 (2)
O4—H4A···O10.82 (2)2.10 (2)2.914 (2)171 (3)
O4—H4B···O4iii0.83 (2)2.03 (2)2.8681 (17)179 (3)
N1—H1···O2ii0.861.812.6683 (19)174
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x, y1, z; (iii) x+1/2, y1/2, z+1/2.
 

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