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In the title compound, C6H9N2+·C10H9O4·H2O, the N atom in the pyridine ring is protonated in preference to the amino N atom. O—H...O, N—H...O and C—H...O interactions generate a three-dimensional molecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022165/ob6300sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022165/ob6300Isup2.hkl
Contains datablock I

CCDC reference: 226975

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.137
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT353_ALERT_3_C Long N-H Bond (0.87A) N1 - H1 = 1.06 Ang. PLAT417_ALERT_2_C Short Inter D-H..H-D H4 .. H5B = 2.12 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H9 N2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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-5-methylpyridinium 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate monohydrate top
Crystal data top
C6H9N2+·C10H9O4·H2OF(000) = 680
Mr = 320.34Dx = 1.330 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8466 reflections
a = 8.2127 (4) Åθ = 2.2–27.5°
b = 17.9985 (10) ŵ = 0.1 mm1
c = 10.8564 (5) ÅT = 293 K
β = 94.603 (3)°Prism, yellow
V = 1599.58 (14) Å30.30 × 0.15 × 0.14 mm
Z = 4
Data collection top
Rigaku RAXIS-RAPID
diffractometer
2100 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.028
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.908, Tmax = 0.986k = 2323
7122 measured reflectionsl = 1414
3666 independent reflections
Refinement top
Refinement on F2All H-atom parameters refined
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0768P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.049(Δ/σ)max < 0.001
wR(F2) = 0.137Δρmax = 0.38 e Å3
S = 0.93Δρmin = 0.22 e Å3
3666 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
289 parametersExtinction coefficient: 0.0077 (16)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O50.6010 (2)0.67946 (9)0.33719 (19)0.0604 (5)
O40.23192 (18)0.57813 (8)0.53665 (14)0.0504 (4)
O30.11664 (18)0.48866 (8)0.36576 (14)0.0535 (4)
O20.4362 (2)0.75899 (8)0.02043 (14)0.0560 (4)
O10.4047 (2)0.65914 (9)0.13358 (15)0.0673 (5)
N20.3662 (2)0.92177 (13)0.05339 (19)0.0512 (5)
N10.5378 (2)0.85842 (9)0.19450 (16)0.0402 (4)
C160.7711 (4)0.9052 (2)0.4957 (3)0.0678 (8)
C150.6375 (3)0.85378 (11)0.3003 (2)0.0431 (5)
C140.6624 (3)0.91167 (12)0.3780 (2)0.0453 (5)
C130.5815 (3)0.97765 (13)0.3424 (2)0.0505 (6)
C120.4845 (3)0.98337 (12)0.2369 (2)0.0497 (6)
C110.4601 (2)0.92143 (10)0.15938 (19)0.0389 (5)
C100.0648 (4)0.43797 (16)0.2708 (3)0.0641 (7)
C90.3765 (2)0.69591 (12)0.0388 (2)0.0449 (5)
C80.2615 (3)0.66137 (13)0.0585 (2)0.0488 (5)
C70.2038 (3)0.69382 (13)0.1592 (2)0.0482 (5)
C60.0445 (2)0.58799 (12)0.2610 (2)0.0433 (5)
C50.0618 (2)0.56017 (11)0.35451 (18)0.0394 (5)
C40.1247 (2)0.60783 (12)0.44811 (18)0.0422 (5)
C30.0777 (3)0.68110 (12)0.4472 (2)0.0520 (6)
C20.0291 (3)0.70835 (13)0.3522 (2)0.0538 (6)
C10.0904 (2)0.66279 (12)0.25861 (19)0.0447 (5)
H16A0.845 (5)0.942 (2)0.502 (4)0.145 (16)*
H16B0.711 (4)0.9019 (19)0.567 (3)0.115 (13)*
H16C0.838 (5)0.862 (2)0.501 (4)0.140 (15)*
H150.684 (2)0.8058 (12)0.3125 (18)0.047 (6)*
H130.595 (3)1.0185 (13)0.394 (2)0.056 (7)*
H120.432 (3)1.0274 (14)0.213 (2)0.063 (7)*
H10A0.099 (4)0.4548 (17)0.184 (3)0.104 (10)*
H10B0.113 (3)0.3924 (13)0.291 (2)0.049 (6)*
H10C0.053 (4)0.4303 (14)0.273 (2)0.075 (8)*
H80.225 (3)0.6096 (15)0.051 (2)0.069 (7)*
H70.243 (3)0.7489 (13)0.165 (2)0.070 (7)*
H60.082 (3)0.5543 (12)0.203 (2)0.049 (6)*
H5A0.541 (3)0.6729 (14)0.272 (3)0.068 (8)*
H5B0.535 (4)0.700 (2)0.396 (3)0.130 (15)*
H40.286 (4)0.6153 (18)0.585 (3)0.096 (10)*
H30.120 (3)0.7157 (13)0.513 (2)0.063 (7)*
H2A0.347 (3)0.8783 (16)0.013 (2)0.074 (8)*
H2B0.313 (3)0.9636 (16)0.034 (3)0.082 (9)*
H20.066 (3)0.7639 (14)0.353 (2)0.069 (7)*
H10.516 (3)0.8130 (15)0.133 (2)0.079 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0752 (12)0.0506 (10)0.0508 (11)0.0060 (8)0.0238 (10)0.0015 (8)
O40.0525 (9)0.0473 (9)0.0473 (9)0.0055 (7)0.0216 (7)0.0039 (7)
O30.0575 (9)0.0484 (9)0.0515 (10)0.0048 (7)0.0155 (7)0.0041 (7)
O20.0743 (10)0.0451 (9)0.0455 (9)0.0094 (8)0.0136 (8)0.0047 (7)
O10.0913 (13)0.0558 (10)0.0498 (10)0.0119 (8)0.0264 (9)0.0060 (8)
N20.0545 (12)0.0499 (12)0.0469 (12)0.0072 (9)0.0093 (9)0.0000 (9)
N10.0453 (9)0.0338 (9)0.0405 (10)0.0007 (7)0.0030 (8)0.0006 (7)
C160.0672 (18)0.083 (2)0.0494 (17)0.0029 (16)0.0172 (14)0.0005 (15)
C150.0469 (12)0.0351 (11)0.0463 (13)0.0002 (9)0.0016 (10)0.0063 (9)
C140.0425 (11)0.0496 (13)0.0428 (12)0.0051 (9)0.0017 (9)0.0008 (10)
C130.0588 (14)0.0410 (12)0.0508 (14)0.0043 (10)0.0011 (11)0.0089 (10)
C120.0578 (13)0.0339 (11)0.0563 (15)0.0068 (10)0.0028 (11)0.0001 (10)
C110.0380 (10)0.0386 (11)0.0396 (12)0.0000 (8)0.0001 (9)0.0034 (9)
C100.0731 (19)0.0534 (15)0.0631 (18)0.0038 (14)0.0109 (15)0.0115 (13)
C90.0488 (12)0.0434 (12)0.0405 (12)0.0021 (9)0.0094 (10)0.0112 (10)
C80.0520 (13)0.0474 (13)0.0449 (13)0.0029 (10)0.0083 (10)0.0054 (10)
C70.0484 (12)0.0469 (12)0.0479 (13)0.0020 (10)0.0055 (10)0.0082 (11)
C60.0397 (11)0.0521 (13)0.0368 (12)0.0041 (9)0.0042 (9)0.0015 (10)
C50.0350 (10)0.0427 (11)0.0398 (12)0.0027 (8)0.0020 (9)0.0053 (9)
C40.0392 (11)0.0494 (12)0.0361 (11)0.0028 (9)0.0082 (9)0.0065 (9)
C30.0569 (13)0.0462 (13)0.0497 (14)0.0050 (10)0.0160 (11)0.0007 (10)
C20.0579 (13)0.0472 (13)0.0534 (14)0.0069 (10)0.0146 (11)0.0038 (11)
C10.0429 (11)0.0484 (12)0.0414 (12)0.0036 (9)0.0052 (9)0.0108 (9)
Geometric parameters (Å, º) top
O4—C41.360 (2)O5—H5A0.84 (3)
O3—C51.366 (2)O5—H5B0.94 (4)
O3—C101.416 (3)O4—H40.94 (3)
O2—C91.259 (3)N2—H2A0.91 (3)
O1—C91.230 (3)N2—H2B0.89 (3)
N2—C111.333 (3)N1—H11.06 (3)
N1—C111.342 (2)C16—H16A0.90 (4)
N1—C151.358 (3)C16—H16B0.95 (4)
C9—C81.494 (3)C16—H16C0.96 (4)
C7—C81.296 (3)C15—H150.95 (2)
C1—C71.477 (3)C13—H130.93 (2)
C15—C141.346 (3)C12—H120.93 (2)
C12—C131.345 (3)C10—H10A1.05 (3)
C11—C121.402 (3)C10—H10B0.93 (2)
C6—C11.398 (3)C10—H10C0.98 (3)
C5—C61.379 (3)C8—H80.98 (3)
C5—C41.397 (3)C7—H71.05 (2)
C4—C31.374 (3)C6—H60.91 (2)
C2—C31.388 (3)C3—H30.99 (2)
C1—C21.370 (3)C2—H21.04 (2)
C5—O3—C10117.67 (18)C11—N1—C15122.21 (18)
O4—C4—C3123.24 (19)C11—N1—H1114.9 (14)
O4—C4—C5116.97 (18)C9—C8—H8120.8 (14)
O3—C5—C6126.35 (18)C8—C7—C1127.8 (2)
O3—C5—C4114.43 (16)C8—C7—H7112.6 (13)
O3—C10—H10B107.2 (14)C7—C8—C9125.2 (2)
O3—C10—H10C108.4 (16)C7—C8—H8114.0 (14)
O3—C10—H10A112.5 (17)C6—C5—C4119.21 (18)
O2—C9—C8119.7 (2)C6—C1—C7122.08 (19)
O1—C9—O2124.61 (19)C5—C6—C1121.2 (2)
O1—C9—C8115.68 (19)C5—C6—H6115.4 (14)
N2—C11—N1118.59 (19)C5—O3—C10117.67 (18)
N2—C11—C12124.06 (19)C4—O4—H4111.3 (18)
N1—C11—C12117.35 (19)C4—C3—C2120.3 (2)
N1—C15—H15112.6 (12)C4—C3—H3121.2 (14)
C15—N1—H1122.9 (14)C3—C4—C5119.79 (18)
C15—C14—C13116.0 (2)C3—C2—H2120.1 (13)
C15—C14—C16121.5 (2)C2—C1—C6118.68 (18)
C14—C16—H16A111 (3)C2—C1—C7119.23 (19)
C14—C16—H16B113 (2)C2—C3—H3118.5 (14)
C14—C16—H16C114 (2)C1—C6—H6123.5 (14)
C14—C15—N1122.24 (19)C1—C7—H7119.6 (13)
C14—C15—H15125.2 (12)C1—C2—C3120.8 (2)
C14—C13—H13118.5 (14)C1—C2—H2119.1 (13)
C13—C14—C16122.4 (2)H16B—C16—H16C104 (3)
C13—C12—C11119.8 (2)H16B—C16—H16A112 (3)
C13—C12—H12122.3 (15)H16C—C16—H16A103 (3)
C12—C13—C14122.4 (2)H10B—C10—H10C106 (2)
C12—C13—H13119.1 (14)H10B—C10—H10A109 (2)
C11—C12—H12117.9 (15)H10C—C10—H10A113 (2)
C11—N2—H2A119.0 (17)H5A—O5—H5B107 (3)
C11—N2—H2B116.3 (18)H2A—N2—H2B124 (2)
O4—C4—C3—C2178.3 (2)C10—O3—C5—C62.3 (3)
O3—C5—C6—C1179.2 (2)C10—O3—C5—C4176.8 (2)
O3—C5—C4—O40.6 (3)C7—C1—C2—C3179.9 (2)
O3—C5—C4—C3179.6 (2)C6—C5—C4—O4178.55 (18)
O2—C9—C8—C76.6 (3)C6—C5—C4—C31.3 (3)
O1—C9—C8—C7172.9 (2)C6—C1—C2—C30.5 (3)
N2—C11—C12—C13179.9 (2)C6—C1—C7—C87.6 (4)
N1—C11—C12—C130.7 (3)C5—C6—C1—C20.8 (3)
N1—C15—C14—C131.0 (3)C5—C4—C3—C21.5 (3)
N1—C15—C14—C16179.0 (2)C5—C6—C1—C7179.9 (2)
C15—N1—C11—N2179.07 (19)C4—C5—C6—C10.2 (3)
C15—N1—C11—C120.3 (3)C2—C1—C7—C8173.0 (2)
C16—C14—C13—C12179.9 (3)C2—C1—C7—C8173.0 (2)
C15—C14—C13—C120.1 (3)C1—C7—C8—C9179.9 (2)
C11—N1—C15—C141.3 (3)C1—C2—C3—C40.6 (4)
C11—C12—C13—C141.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O10.84 (3)1.82 (3)2.655 (2)178 (3)
O5—H5B···O2i0.94 (4)1.79 (4)2.729 (3)171 (3)
O4—H4···O5ii0.94 (3)1.67 (3)2.604 (2)174 (3)
N2—H2A···O20.91 (3)2.27 (3)3.013 (3)139 (2)
N2—H2B···O4iii0.89 (3)2.17 (3)3.023 (3)162 (2)
N2—H2B···O3iii0.89 (3)2.39 (3)3.021 (2)129 (2)
N1—H1···O21.06 (3)1.66 (3)2.687 (2)162 (2)
N1—H1···O11.06 (3)2.91 (3)3.792 (2)140.4 (18)
C16—H16B···O1i0.95 (4)2.89 (4)3.654 (4)138 (3)
C15—H15···O50.95 (2)2.40 (2)3.180 (3)139.7 (16)
C13—H13···O1iv0.93 (2)2.55 (2)3.278 (3)136.0 (18)
C12—H12···O5iv0.93 (2)2.80 (2)3.675 (3)157.4 (19)
C10—H10C···O4v0.98 (3)2.64 (3)3.348 (4)130 (2)
C12—H12···O4iii0.93 (2)2.59 (2)3.349 (3)139.6 (19)
C7—H7···O21.05 (2)2.47 (2)2.868 (2)101.6 (15)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y, z+1; (iii) x, y+1/2, z+1/2; (iv) x1, y+1/2, z1/2; (v) x, y+1, z+1.
 

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