2-Amino-6-methyl­pyridinium 2-formyl­benzoate monohydrate

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.

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

No syntax errors found



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

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

Crystal data

C6H9N2^+·C8H5O3^−·H2O	F(000) = 1168
Mr = 276.29	Dx = 1.341 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14925 reflections
a = 34.171 (3) Å	θ = 1.4–25.1°
b = 4.9220 (3) Å	µ = 0.10 mm^−1
c = 19.4423 (17) Å	T = 296 K
β = 123.172 (6)°	Prism, colourless
V = 2737.1 (4) Å^3	0.71 × 0.38 × 0.12 mm
Z = 8

Data collection

STOE IPDS 2 diffractometer	2400 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1794 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 6.67 pixels mm^-1	θmax = 25.1°, θmin = 1.4°
ω scan	h = −40→40
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.949, Tmax = 0.991	l = −22→22
14999 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0679P)^2 + 0.2766P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2400 reflections	Δρmax = 0.23 e Å^−3
199 parameters	Δρmin = −0.18 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (9)

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.37513 (6)	0.4018 (3)	0.48108 (10)	0.0464 (4)
C2	0.42262 (6)	0.4310 (3)	0.50971 (10)	0.0498 (4)
C3	0.44175 (7)	0.2674 (4)	0.47689 (12)	0.0612 (5)
H3	0.4730	0.2880	0.4950	0.073*
C4	0.41502 (8)	0.0762 (4)	0.41807 (13)	0.0667 (5)
H4	0.4282	−0.0315	0.3966	0.080*
C5	0.36879 (8)	0.0439 (4)	0.39092 (12)	0.0635 (5)
H5	0.3508	−0.0876	0.3517	0.076*
C6	0.34902 (7)	0.2059 (4)	0.42172 (11)	0.0545 (4)
H6	0.3176	0.1839	0.4024	0.065*
C7	0.35212 (6)	0.5721 (3)	0.51371 (10)	0.0481 (4)
C8	0.45341 (7)	0.6404 (4)	0.56985 (12)	0.0618 (5)
H8	0.4397	0.7911	0.5773	0.074*
C9	0.31534 (6)	0.1379 (3)	0.62118 (11)	0.0486 (4)
C10	0.30461 (7)	0.3376 (4)	0.65971 (12)	0.0566 (5)
H10	0.2737	0.3749	0.6414	0.068*
C11	0.34020 (7)	0.4759 (4)	0.72435 (12)	0.0611 (5)
H11	0.3334	0.6095	0.7501	0.073*
C12	0.38653 (7)	0.4212 (4)	0.75258 (11)	0.0593 (5)
H12	0.4105	0.5172	0.7969	0.071*
C13	0.39655 (6)	0.2262 (4)	0.71487 (10)	0.0525 (4)
C14	0.44424 (7)	0.1488 (5)	0.73689 (14)	0.0734 (6)
H14A	0.4474	0.1913	0.6920	0.088*
H14B	0.4488	−0.0425	0.7481	0.088*
H14C	0.4672	0.2479	0.7848	0.088*
N1	0.36046 (5)	0.0876 (3)	0.65069 (9)	0.0481 (4)
H1	0.3670	−0.0387	0.6279	0.058*
N2	0.28339 (6)	−0.0062 (3)	0.55626 (11)	0.0608 (4)
O1	0.30863 (4)	0.6029 (3)	0.46957 (8)	0.0632 (4)
O2	0.37815 (5)	0.6702 (3)	0.58409 (8)	0.0633 (4)
O3	0.49526 (6)	0.6246 (4)	0.60939 (11)	0.0975 (6)
O4	0.25579 (6)	0.6896 (3)	0.29248 (10)	0.0760 (5)
H2A	0.2549 (9)	−0.001 (5)	0.5438 (14)	0.075 (7)*
H2B	0.2940 (8)	−0.131 (5)	0.5346 (14)	0.078 (7)*
H4A	0.2722 (8)	0.651 (5)	0.3414 (11)	0.089 (8)*
H4B	0.2520 (10)	0.545 (4)	0.2674 (17)	0.104 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0503 (9)	0.0436 (8)	0.0459 (9)	0.0031 (7)	0.0266 (8)	0.0070 (7)
C2	0.0509 (10)	0.0494 (9)	0.0489 (9)	0.0031 (7)	0.0272 (8)	0.0071 (7)
C3	0.0596 (11)	0.0641 (11)	0.0680 (11)	0.0090 (9)	0.0401 (10)	0.0085 (10)
C4	0.0844 (15)	0.0603 (11)	0.0667 (12)	0.0145 (11)	0.0486 (12)	0.0028 (9)
C5	0.0778 (14)	0.0516 (10)	0.0561 (11)	0.0039 (9)	0.0334 (10)	−0.0031 (8)
C6	0.0551 (10)	0.0493 (9)	0.0536 (10)	−0.0016 (8)	0.0261 (9)	0.0009 (8)
C7	0.0493 (10)	0.0473 (9)	0.0509 (10)	0.0006 (7)	0.0294 (9)	0.0033 (7)
C8	0.0578 (12)	0.0663 (12)	0.0601 (11)	−0.0063 (9)	0.0315 (10)	0.0001 (9)
C9	0.0461 (9)	0.0459 (9)	0.0529 (9)	−0.0009 (7)	0.0265 (8)	0.0022 (7)
C10	0.0553 (11)	0.0551 (10)	0.0654 (11)	0.0038 (8)	0.0368 (10)	0.0006 (9)
C11	0.0748 (13)	0.0559 (10)	0.0619 (11)	0.0004 (9)	0.0434 (11)	−0.0052 (9)
C12	0.0640 (12)	0.0582 (11)	0.0500 (10)	−0.0074 (9)	0.0275 (9)	−0.0063 (8)
C13	0.0483 (10)	0.0557 (10)	0.0472 (9)	−0.0052 (8)	0.0223 (8)	0.0020 (8)
C14	0.0466 (11)	0.0877 (15)	0.0712 (13)	−0.0038 (10)	0.0227 (10)	−0.0092 (11)
N1	0.0441 (8)	0.0483 (8)	0.0508 (8)	−0.0005 (6)	0.0253 (7)	−0.0022 (6)
N2	0.0430 (9)	0.0605 (10)	0.0724 (11)	−0.0044 (7)	0.0275 (8)	−0.0156 (8)
O1	0.0489 (8)	0.0750 (9)	0.0668 (8)	0.0026 (6)	0.0325 (7)	−0.0054 (6)
O2	0.0636 (8)	0.0696 (8)	0.0538 (7)	0.0080 (6)	0.0303 (7)	−0.0068 (6)
O3	0.0549 (10)	0.1075 (14)	0.0928 (12)	−0.0070 (8)	0.0165 (9)	−0.0067 (10)
O4	0.0941 (12)	0.0596 (9)	0.0636 (9)	0.0079 (8)	0.0363 (9)	0.0053 (8)

Geometric parameters (Å, º)

C1—C6	1.389 (2)	C9—C10	1.401 (3)
C1—C2	1.405 (2)	C10—C11	1.360 (3)
C1—C7	1.506 (2)	C10—H10	0.9300
C2—C3	1.393 (3)	C11—C12	1.389 (3)
C2—C8	1.480 (3)	C11—H11	0.9300
C3—C4	1.373 (3)	C12—C13	1.361 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (3)	C13—N1	1.364 (2)
C4—H4	0.9300	C13—C14	1.490 (3)
C5—C6	1.376 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O2	1.251 (2)	N1—H1	0.8600
C7—O1	1.254 (2)	N2—H2A	0.87 (2)
C8—O3	1.200 (2)	N2—H2B	0.92 (3)
C8—H8	0.9300	O4—H4A	0.820 (17)
C9—N2	1.334 (2)	O4—H4B	0.834 (17)
C9—N1	1.341 (2)
C6—C1—C2	118.52 (16)	N1—C9—C10	118.46 (16)
C6—C1—C7	119.35 (15)	C11—C10—C9	118.83 (17)
C2—C1—C7	122.13 (15)	C11—C10—H10	120.6
C3—C2—C1	119.29 (17)	C9—C10—H10	120.6
C3—C2—C8	117.09 (17)	C10—C11—C12	121.17 (17)
C1—C2—C8	123.50 (16)	C10—C11—H11	119.4
C4—C3—C2	120.85 (19)	C12—C11—H11	119.4
C4—C3—H3	119.6	C13—C12—C11	119.49 (17)
C2—C3—H3	119.6	C13—C12—H12	120.3
C3—C4—C5	120.04 (18)	C11—C12—H12	120.3
C3—C4—H4	120.0	C12—C13—N1	118.53 (17)
C5—C4—H4	120.0	C12—C13—C14	125.70 (17)
C4—C5—C6	120.05 (19)	N1—C13—C14	115.77 (17)
C4—C5—H5	120.0	C13—C14—H14A	109.5
C6—C5—H5	120.0	C13—C14—H14B	109.5
C5—C6—C1	121.24 (18)	H14A—C14—H14B	109.5
C5—C6—H6	119.4	C13—C14—H14C	109.5
C1—C6—H6	119.4	H14A—C14—H14C	109.5
O2—C7—O1	124.67 (16)	H14B—C14—H14C	109.5
O2—C7—C1	116.94 (15)	C9—N1—C13	123.49 (15)
O1—C7—C1	118.38 (15)	C9—N1—H1	118.3
O3—C8—C2	123.0 (2)	C13—N1—H1	118.3
O3—C8—H8	118.5	C9—N2—H2A	117.5 (15)
C2—C8—H8	118.5	C9—N2—H2B	117.5 (14)
N2—C9—N1	117.44 (16)	H2A—N2—H2B	124 (2)
N2—C9—C10	124.11 (17)	H4A—O4—H4B	106 (3)
C6—C1—C2—C3	1.2 (2)	C2—C1—C7—O1	156.85 (16)
C7—C1—C2—C3	−179.90 (15)	C3—C2—C8—O3	−23.4 (3)
C6—C1—C2—C8	177.07 (16)	C1—C2—C8—O3	160.6 (2)
C7—C1—C2—C8	−4.0 (2)	N2—C9—C10—C11	−178.46 (18)
C1—C2—C3—C4	−1.0 (3)	N1—C9—C10—C11	1.2 (3)
C8—C2—C3—C4	−177.14 (18)	C9—C10—C11—C12	−0.3 (3)
C2—C3—C4—C5	−0.1 (3)	C10—C11—C12—C13	0.1 (3)
C3—C4—C5—C6	1.0 (3)	C11—C12—C13—N1	−0.8 (3)
C4—C5—C6—C1	−0.8 (3)	C11—C12—C13—C14	178.67 (19)
C2—C1—C6—C5	−0.3 (3)	N2—C9—N1—C13	177.73 (16)
C7—C1—C6—C5	−179.26 (16)	C10—C9—N1—C13	−2.0 (3)
C6—C1—C7—O2	154.87 (16)	C12—C13—N1—C9	1.7 (3)
C2—C1—C7—O2	−24.0 (2)	C14—C13—N1—C9	−177.74 (17)
C6—C1—C7—O1	−24.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^i	0.87 (2)	2.10 (2)	2.939 (2)	163 (2)
N2—H2B···O1^ii	0.92 (3)	2.06 (3)	2.980 (2)	171 (2)
O4—H4A···O1	0.82 (2)	2.10 (2)	2.914 (2)	171 (3)
O4—H4B···O4^iii	0.83 (2)	2.03 (2)	2.8681 (17)	179 (3)
N1—H1···O2^ii	0.86	1.81	2.6683 (19)	174

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