2-Amino-5-methylpyridinium 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate monohydrate

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.

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

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Computing details

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

Crystal data

C6H9N2^+·C10H9O4^−·H2O	F(000) = 680
Mr = 320.34	Dx = 1.330 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8466 reflections
a = 8.2127 (4) Å	θ = 2.2–27.5°
b = 17.9985 (10) Å	µ = 0.1 mm^−1
c = 10.8564 (5) Å	T = 293 K
β = 94.603 (3)°	Prism, yellow
V = 1599.58 (14) Å^3	0.30 × 0.15 × 0.14 mm
Z = 4

Data collection

Rigaku RAXIS-RAPID diffractometer	2100 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.908, Tmax = 0.986	k = −23→23
7122 measured reflections	l = −14→14
3666 independent reflections

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0768P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max < 0.001
wR(F^2) = 0.137	Δρmax = 0.38 e Å^−3
S = 0.93	Δρmin = −0.22 e Å^−3
3666 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
289 parameters	Extinction coefficient: 0.0077 (16)
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O5	−0.6010 (2)	0.67946 (9)	−0.33719 (19)	0.0604 (5)
O4	0.23192 (18)	0.57813 (8)	0.53665 (14)	0.0504 (4)
O3	0.11664 (18)	0.48866 (8)	0.36576 (14)	0.0535 (4)
O2	−0.4362 (2)	0.75899 (8)	−0.02043 (14)	0.0560 (4)
O1	−0.4047 (2)	0.65914 (9)	−0.13358 (15)	0.0673 (5)
N2	−0.3662 (2)	0.92177 (13)	−0.05339 (19)	0.0512 (5)
N1	−0.5378 (2)	0.85842 (9)	−0.19450 (16)	0.0402 (4)
C16	−0.7711 (4)	0.9052 (2)	−0.4957 (3)	0.0678 (8)
C15	−0.6375 (3)	0.85378 (11)	−0.3003 (2)	0.0431 (5)
C14	−0.6624 (3)	0.91167 (12)	−0.3780 (2)	0.0453 (5)
C13	−0.5815 (3)	0.97765 (13)	−0.3424 (2)	0.0505 (6)
C12	−0.4845 (3)	0.98337 (12)	−0.2369 (2)	0.0497 (6)
C11	−0.4601 (2)	0.92143 (10)	−0.15938 (19)	0.0389 (5)
C10	0.0648 (4)	0.43797 (16)	0.2708 (3)	0.0641 (7)
C9	−0.3765 (2)	0.69591 (12)	−0.0388 (2)	0.0449 (5)
C8	−0.2615 (3)	0.66137 (13)	0.0585 (2)	0.0488 (5)
C7	−0.2038 (3)	0.69382 (13)	0.1592 (2)	0.0482 (5)
C6	−0.0445 (2)	0.58799 (12)	0.2610 (2)	0.0433 (5)
C5	0.0618 (2)	0.56017 (11)	0.35451 (18)	0.0394 (5)
C4	0.1247 (2)	0.60783 (12)	0.44811 (18)	0.0422 (5)
C3	0.0777 (3)	0.68110 (12)	0.4472 (2)	0.0520 (6)
C2	−0.0291 (3)	0.70835 (13)	0.3522 (2)	0.0538 (6)
C1	−0.0904 (2)	0.66279 (12)	0.25861 (19)	0.0447 (5)
H16A	−0.845 (5)	0.942 (2)	−0.502 (4)	0.145 (16)*
H16B	−0.711 (4)	0.9019 (19)	−0.567 (3)	0.115 (13)*
H16C	−0.838 (5)	0.862 (2)	−0.501 (4)	0.140 (15)*
H15	−0.684 (2)	0.8058 (12)	−0.3125 (18)	0.047 (6)*
H13	−0.595 (3)	1.0185 (13)	−0.394 (2)	0.056 (7)*
H12	−0.432 (3)	1.0274 (14)	−0.213 (2)	0.063 (7)*
H10A	0.099 (4)	0.4548 (17)	0.184 (3)	0.104 (10)*
H10B	0.113 (3)	0.3924 (13)	0.291 (2)	0.049 (6)*
H10C	−0.053 (4)	0.4303 (14)	0.273 (2)	0.075 (8)*
H8	−0.225 (3)	0.6096 (15)	0.051 (2)	0.069 (7)*
H7	−0.243 (3)	0.7489 (13)	0.165 (2)	0.070 (7)*
H6	−0.082 (3)	0.5543 (12)	0.203 (2)	0.049 (6)*
H5A	−0.541 (3)	0.6729 (14)	−0.272 (3)	0.068 (8)*
H5B	−0.535 (4)	0.700 (2)	−0.396 (3)	0.130 (15)*
H4	0.286 (4)	0.6153 (18)	0.585 (3)	0.096 (10)*
H3	0.120 (3)	0.7157 (13)	0.513 (2)	0.063 (7)*
H2A	−0.347 (3)	0.8783 (16)	−0.013 (2)	0.074 (8)*
H2B	−0.313 (3)	0.9636 (16)	−0.034 (3)	0.082 (9)*
H2	−0.066 (3)	0.7639 (14)	0.353 (2)	0.069 (7)*
H1	−0.516 (3)	0.8130 (15)	−0.133 (2)	0.079 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0752 (12)	0.0506 (10)	0.0508 (11)	−0.0060 (8)	−0.0238 (10)	0.0015 (8)
O4	0.0525 (9)	0.0473 (9)	0.0473 (9)	0.0055 (7)	−0.0216 (7)	0.0039 (7)
O3	0.0575 (9)	0.0484 (9)	0.0515 (10)	0.0048 (7)	−0.0155 (7)	−0.0041 (7)
O2	0.0743 (10)	0.0451 (9)	0.0455 (9)	0.0094 (8)	−0.0136 (8)	0.0047 (7)
O1	0.0913 (13)	0.0558 (10)	0.0498 (10)	0.0119 (8)	−0.0264 (9)	−0.0060 (8)
N2	0.0545 (12)	0.0499 (12)	0.0469 (12)	−0.0072 (9)	−0.0093 (9)	0.0000 (9)
N1	0.0453 (9)	0.0338 (9)	0.0405 (10)	0.0007 (7)	−0.0030 (8)	−0.0006 (7)
C16	0.0672 (18)	0.083 (2)	0.0494 (17)	0.0029 (16)	−0.0172 (14)	0.0005 (15)
C15	0.0469 (12)	0.0351 (11)	0.0463 (13)	−0.0002 (9)	−0.0016 (10)	−0.0063 (9)
C14	0.0425 (11)	0.0496 (13)	0.0428 (12)	0.0051 (9)	−0.0017 (9)	−0.0008 (10)
C13	0.0588 (14)	0.0410 (12)	0.0508 (14)	0.0043 (10)	−0.0011 (11)	0.0089 (10)
C12	0.0578 (13)	0.0339 (11)	0.0563 (15)	−0.0068 (10)	−0.0028 (11)	0.0001 (10)
C11	0.0380 (10)	0.0386 (11)	0.0396 (12)	0.0000 (8)	−0.0001 (9)	−0.0034 (9)
C10	0.0731 (19)	0.0534 (15)	0.0631 (18)	0.0038 (14)	−0.0109 (15)	−0.0115 (13)
C9	0.0488 (12)	0.0434 (12)	0.0405 (12)	−0.0021 (9)	−0.0094 (10)	0.0112 (10)
C8	0.0520 (13)	0.0474 (13)	0.0449 (13)	0.0029 (10)	−0.0083 (10)	0.0054 (10)
C7	0.0484 (12)	0.0469 (12)	0.0479 (13)	0.0020 (10)	−0.0055 (10)	0.0082 (11)
C6	0.0397 (11)	0.0521 (13)	0.0368 (12)	−0.0041 (9)	−0.0042 (9)	−0.0015 (10)
C5	0.0350 (10)	0.0427 (11)	0.0398 (12)	0.0027 (8)	−0.0020 (9)	0.0053 (9)
C4	0.0392 (11)	0.0494 (12)	0.0361 (11)	0.0028 (9)	−0.0082 (9)	0.0065 (9)
C3	0.0569 (13)	0.0462 (13)	0.0497 (14)	0.0050 (10)	−0.0160 (11)	−0.0007 (10)
C2	0.0579 (13)	0.0472 (13)	0.0534 (14)	0.0069 (10)	−0.0146 (11)	0.0038 (11)
C1	0.0429 (11)	0.0484 (12)	0.0414 (12)	0.0036 (9)	−0.0052 (9)	0.0108 (9)

Geometric parameters (Å, º)

O4—C4	1.360 (2)	O5—H5A	0.84 (3)
O3—C5	1.366 (2)	O5—H5B	0.94 (4)
O3—C10	1.416 (3)	O4—H4	0.94 (3)
O2—C9	1.259 (3)	N2—H2A	0.91 (3)
O1—C9	1.230 (3)	N2—H2B	0.89 (3)
N2—C11	1.333 (3)	N1—H1	1.06 (3)
N1—C11	1.342 (2)	C16—H16A	0.90 (4)
N1—C15	1.358 (3)	C16—H16B	0.95 (4)
C9—C8	1.494 (3)	C16—H16C	0.96 (4)
C7—C8	1.296 (3)	C15—H15	0.95 (2)
C1—C7	1.477 (3)	C13—H13	0.93 (2)
C15—C14	1.346 (3)	C12—H12	0.93 (2)
C12—C13	1.345 (3)	C10—H10A	1.05 (3)
C11—C12	1.402 (3)	C10—H10B	0.93 (2)
C6—C1	1.398 (3)	C10—H10C	0.98 (3)
C5—C6	1.379 (3)	C8—H8	0.98 (3)
C5—C4	1.397 (3)	C7—H7	1.05 (2)
C4—C3	1.374 (3)	C6—H6	0.91 (2)
C2—C3	1.388 (3)	C3—H3	0.99 (2)
C1—C2	1.370 (3)	C2—H2	1.04 (2)
C5—O3—C10	117.67 (18)	C11—N1—C15	122.21 (18)
O4—C4—C3	123.24 (19)	C11—N1—H1	114.9 (14)
O4—C4—C5	116.97 (18)	C9—C8—H8	120.8 (14)
O3—C5—C6	126.35 (18)	C8—C7—C1	127.8 (2)
O3—C5—C4	114.43 (16)	C8—C7—H7	112.6 (13)
O3—C10—H10B	107.2 (14)	C7—C8—C9	125.2 (2)
O3—C10—H10C	108.4 (16)	C7—C8—H8	114.0 (14)
O3—C10—H10A	112.5 (17)	C6—C5—C4	119.21 (18)
O2—C9—C8	119.7 (2)	C6—C1—C7	122.08 (19)
O1—C9—O2	124.61 (19)	C5—C6—C1	121.2 (2)
O1—C9—C8	115.68 (19)	C5—C6—H6	115.4 (14)
N2—C11—N1	118.59 (19)	C5—O3—C10	117.67 (18)
N2—C11—C12	124.06 (19)	C4—O4—H4	111.3 (18)
N1—C11—C12	117.35 (19)	C4—C3—C2	120.3 (2)
N1—C15—H15	112.6 (12)	C4—C3—H3	121.2 (14)
C15—N1—H1	122.9 (14)	C3—C4—C5	119.79 (18)
C15—C14—C13	116.0 (2)	C3—C2—H2	120.1 (13)
C15—C14—C16	121.5 (2)	C2—C1—C6	118.68 (18)
C14—C16—H16A	111 (3)	C2—C1—C7	119.23 (19)
C14—C16—H16B	113 (2)	C2—C3—H3	118.5 (14)
C14—C16—H16C	114 (2)	C1—C6—H6	123.5 (14)
C14—C15—N1	122.24 (19)	C1—C7—H7	119.6 (13)
C14—C15—H15	125.2 (12)	C1—C2—C3	120.8 (2)
C14—C13—H13	118.5 (14)	C1—C2—H2	119.1 (13)
C13—C14—C16	122.4 (2)	H16B—C16—H16C	104 (3)
C13—C12—C11	119.8 (2)	H16B—C16—H16A	112 (3)
C13—C12—H12	122.3 (15)	H16C—C16—H16A	103 (3)
C12—C13—C14	122.4 (2)	H10B—C10—H10C	106 (2)
C12—C13—H13	119.1 (14)	H10B—C10—H10A	109 (2)
C11—C12—H12	117.9 (15)	H10C—C10—H10A	113 (2)
C11—N2—H2A	119.0 (17)	H5A—O5—H5B	107 (3)
C11—N2—H2B	116.3 (18)	H2A—N2—H2B	124 (2)
O4—C4—C3—C2	178.3 (2)	C10—O3—C5—C6	2.3 (3)
O3—C5—C6—C1	−179.2 (2)	C10—O3—C5—C4	−176.8 (2)
O3—C5—C4—O4	0.6 (3)	C7—C1—C2—C3	179.9 (2)
O3—C5—C4—C3	−179.6 (2)	C6—C5—C4—O4	−178.55 (18)
O2—C9—C8—C7	−6.6 (3)	C6—C5—C4—C3	1.3 (3)
O1—C9—C8—C7	172.9 (2)	C6—C1—C2—C3	0.5 (3)
N2—C11—C12—C13	179.9 (2)	C6—C1—C7—C8	−7.6 (4)
N1—C11—C12—C13	−0.7 (3)	C5—C6—C1—C2	−0.8 (3)
N1—C15—C14—C13	−1.0 (3)	C5—C4—C3—C2	−1.5 (3)
N1—C15—C14—C16	179.0 (2)	C5—C6—C1—C7	179.9 (2)
C15—N1—C11—N2	179.07 (19)	C4—C5—C6—C1	−0.2 (3)
C15—N1—C11—C12	−0.3 (3)	C2—C1—C7—C8	173.0 (2)
C16—C14—C13—C12	179.9 (3)	C2—C1—C7—C8	173.0 (2)
C15—C14—C13—C12	−0.1 (3)	C1—C7—C8—C9	179.9 (2)
C11—N1—C15—C14	1.3 (3)	C1—C2—C3—C4	0.6 (4)
C11—C12—C13—C14	1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.84 (3)	1.82 (3)	2.655 (2)	178 (3)
O5—H5B···O2^i	0.94 (4)	1.79 (4)	2.729 (3)	171 (3)
O4—H4···O5^ii	0.94 (3)	1.67 (3)	2.604 (2)	174 (3)
N2—H2A···O2	0.91 (3)	2.27 (3)	3.013 (3)	139 (2)
N2—H2B···O4^iii	0.89 (3)	2.17 (3)	3.023 (3)	162 (2)
N2—H2B···O3^iii	0.89 (3)	2.39 (3)	3.021 (2)	129 (2)
N1—H1···O2	1.06 (3)	1.66 (3)	2.687 (2)	162 (2)
N1—H1···O1	1.06 (3)	2.91 (3)	3.792 (2)	140.4 (18)
C16—H16B···O1^i	0.95 (4)	2.89 (4)	3.654 (4)	138 (3)
C15—H15···O5	0.95 (2)	2.40 (2)	3.180 (3)	139.7 (16)
C13—H13···O1^iv	0.93 (2)	2.55 (2)	3.278 (3)	136.0 (18)
C12—H12···O5^iv	0.93 (2)	2.80 (2)	3.675 (3)	157.4 (19)
C10—H10C···O4^v	0.98 (3)	2.64 (3)	3.348 (4)	130 (2)
C12—H12···O4^iii	0.93 (2)	2.59 (2)	3.349 (3)	139.6 (19)
C7—H7···O2	1.05 (2)	2.47 (2)	2.868 (2)	101.6 (15)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, y, z+1; (iii) −x, y+1/2, −z+1/2; (iv) −x−1, y+1/2, −z−1/2; (v) −x, −y+1, −z+1.