2-Amino-3-(hy-droxy-meth-yl)pyridinium 2-benzoyl-benzoate monohydrate.

In the title hydrated salt, C(6)H(9)N(2)O(+)·C(14)H(9)O(3) (-)·H(2)O, the dihedral angle between the benzene rings of the 2-benzoyl-benzoate anion is 82.04 (14)°, while the angles between the aromatic ring of the pyridinium cation and each of the benzene rings of the anion are 4.42 (14) and 82.04 (14)°. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, generating a three-dimensional network with R(2) (2)(8), R(6) (6)(16) and R(4) (4)(6) motifs. The crystal packing is further stabilized by two π-π inter-actions, one between pyridinium rings, and another between the benzene benzoate and pyridinium rings of neighbouring mol-ecules, with centroid-to-centroid distances of 3.559 (2) and 3.606 (2) Å, respectively.

Related literature

For general background, see: Lehn (1990 ▶); Mrozek & Glowiak (2004 ▶); Yang et al. (1995 ▶); Goswami & Ghosh (1997 ▶); Goswami et al. (1998 ▶); Lah et al. (2001 ▶); Hong & Sun (2008 ▶). For related structures, see: Büyükgüngör & Odabaşoğlu (2002 ▶); Büyükgüngör et al. (2004 ▶); Odabaşoğlu & Büyükgüngör (2007 ▶, 2008 ▶); Odabaşoğlu et al. (2003b ▶,c ▶). For the synthesis of the title compound, see: Odabaşoğlu et al. (2003a ▶). For ring-motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C6H9N2O+·C14H9O3 −·H2O

M = 368.38

Monoclinic,

a = 15.9259 (11) Å

b = 8.4898 (4) Å

c = 27.6362 (19) Å

β = 93.468 (5)°

V = 3729.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.35 × 0.30 × 0.26 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.967, T max = 0.976

9399 measured reflections

3523 independent reflections

1792 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.156

S = 0.95

3503 reflections

254 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005612/lr2047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005612/lr2047Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005612/lr2047Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H9N2O+·C14H9O3−·H2O	F(000) = 1552
Mr = 368.38	Dx = 1.312 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8608 reflections
a = 15.9259 (11) Å	θ = 1.5–26.1°
b = 8.4898 (4) Å	µ = 0.10 mm−1
c = 27.6362 (19) Å	T = 296 K
β = 93.468 (5)°	Block, colourless
V = 3729.8 (4) Å3	0.35 × 0.30 × 0.26 mm
Z = 8

Stoe IPDS 2 diffractometer	3523 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.117
Detector resolution: 6.67 pixels mm-1	θmax = 25.7°, θmin = 1.5°
ω–scan rotation method	h = −19→15
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→10
Tmin = 0.967, Tmax = 0.976	l = −33→33
9399 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0625P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
3503 reflections	Δρmax = 0.18 e Å−3
254 parameters	Δρmin = −0.21 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (5)

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.

	x	y	z	Uiso*/Ueq
C1	0.40651 (19)	0.3876 (3)	0.66050 (9)	0.0562 (7)
C2	0.4022 (2)	0.2387 (4)	0.68081 (10)	0.0692 (9)
H2	0.3510	0.2001	0.6902	0.083*
C3	0.4738 (3)	0.1478 (4)	0.68716 (11)	0.0788 (10)
H3	0.4705	0.0477	0.7006	0.095*
C4	0.5489 (2)	0.2034 (4)	0.67396 (11)	0.0755 (10)
H4	0.5970	0.1420	0.6788	0.091*
C5	0.5540 (2)	0.3510 (4)	0.65331 (10)	0.0653 (8)
H5	0.6058	0.3881	0.6443	0.078*
C6	0.48330 (18)	0.4444 (3)	0.64586 (8)	0.0542 (7)
C7	0.4857 (2)	0.5976 (4)	0.61819 (9)	0.0591 (8)
C8	0.32807 (19)	0.4875 (4)	0.65745 (9)	0.0595 (8)
C9	0.32802 (18)	0.6335 (4)	0.68740 (9)	0.0553 (7)
C10	0.27551 (19)	0.7577 (4)	0.67355 (11)	0.0652 (8)
H10	0.2441	0.7532	0.6441	0.078*
C11	0.2694 (2)	0.8874 (4)	0.70280 (13)	0.0767 (10)
H11	0.2342	0.9705	0.6931	0.092*
C12	0.3152 (2)	0.8940 (5)	0.74628 (13)	0.0819 (10)
H12	0.3106	0.9812	0.7663	0.098*
C13	0.3682 (2)	0.7722 (5)	0.76063 (11)	0.0818 (10)
H13	0.3990	0.7771	0.7903	0.098*
C14	0.3757 (2)	0.6423 (4)	0.73080 (10)	0.0689 (9)
H14	0.4126	0.5613	0.7400	0.083*
O1	0.55266 (16)	0.6753 (3)	0.61989 (8)	0.0810 (7)
O2	0.41975 (14)	0.6353 (2)	0.59401 (7)	0.0673 (6)
O3	0.26539 (15)	0.4449 (3)	0.63399 (8)	0.0821 (7)
C15	0.5523 (2)	0.8106 (3)	0.45397 (9)	0.0591 (8)
C16	0.5503 (2)	0.9647 (4)	0.43366 (9)	0.0580 (7)
C17	0.4025 (2)	0.9701 (5)	0.43705 (11)	0.0734 (9)
H17	0.3523	1.0245	0.4307	0.088*
C18	0.4010 (2)	0.8251 (5)	0.45727 (12)	0.0778 (10)
H18	0.3508	0.7790	0.4653	0.093*
C19	0.4776 (2)	0.7474 (4)	0.46559 (10)	0.0730 (9)
H19	0.4776	0.6480	0.4797	0.088*
C20	0.6347 (2)	0.7288 (4)	0.46227 (11)	0.0695 (9)
H20A	0.6627	0.7266	0.4321	0.083*
H20B	0.6698	0.7890	0.4855	0.083*
N1	0.47595 (17)	1.0371 (3)	0.42587 (8)	0.0639 (7)
H1	0.4748	1.1297	0.4133	0.077*
N2	0.61927 (17)	1.0410 (3)	0.42175 (8)	0.0683 (7)
H2A	0.6152	1.1340	0.4094	0.082*
H2B	0.6678	0.9973	0.4264	0.082*
O4	0.62787 (17)	0.5725 (3)	0.47963 (7)	0.0814 (7)
H4A	0.619 (3)	0.514 (4)	0.4545 (11)	0.122*
O5	0.70194 (16)	0.5481 (4)	0.57409 (9)	0.0921 (8)
H5A	0.673 (3)	0.560 (5)	0.5473 (9)	0.138*
H5B	0.682 (3)	0.614 (5)	0.5941 (12)	0.138*

	U11	U22	U33	U12	U13	U23
C1	0.0573 (19)	0.0569 (18)	0.0540 (14)	0.0035 (15)	−0.0003 (12)	−0.0019 (13)
C2	0.071 (2)	0.064 (2)	0.0729 (18)	−0.0044 (19)	0.0066 (16)	0.0111 (15)
C3	0.099 (3)	0.065 (2)	0.0708 (19)	0.008 (2)	−0.0016 (18)	0.0184 (16)
C4	0.077 (3)	0.077 (2)	0.0709 (18)	0.019 (2)	−0.0068 (17)	0.0096 (17)
C5	0.060 (2)	0.073 (2)	0.0624 (16)	0.0054 (18)	−0.0011 (14)	0.0028 (15)
C6	0.0581 (19)	0.0530 (17)	0.0508 (13)	0.0011 (16)	−0.0013 (12)	0.0000 (12)
C7	0.060 (2)	0.065 (2)	0.0524 (14)	−0.0022 (18)	0.0044 (14)	−0.0041 (13)
C8	0.0519 (19)	0.069 (2)	0.0577 (15)	−0.0028 (16)	0.0015 (14)	0.0013 (14)
C9	0.0474 (17)	0.0605 (18)	0.0587 (15)	−0.0024 (15)	0.0077 (12)	−0.0002 (13)
C10	0.0555 (19)	0.070 (2)	0.0700 (17)	0.0042 (18)	0.0025 (14)	−0.0030 (16)
C11	0.064 (2)	0.065 (2)	0.102 (3)	0.0034 (18)	0.0106 (18)	−0.0143 (18)
C12	0.077 (3)	0.080 (2)	0.090 (2)	−0.004 (2)	0.0145 (19)	−0.0252 (19)
C13	0.086 (3)	0.098 (3)	0.0616 (17)	−0.011 (2)	0.0015 (17)	−0.0127 (19)
C14	0.072 (2)	0.072 (2)	0.0623 (17)	0.0015 (18)	−0.0006 (15)	0.0027 (16)
O1	0.0715 (16)	0.0775 (16)	0.0936 (15)	−0.0159 (14)	0.0010 (12)	0.0102 (12)
O2	0.0696 (15)	0.0594 (13)	0.0715 (11)	0.0024 (11)	−0.0063 (11)	0.0074 (10)
O3	0.0630 (15)	0.0853 (16)	0.0960 (15)	0.0009 (14)	−0.0107 (12)	−0.0177 (13)
C15	0.074 (2)	0.0551 (17)	0.0477 (13)	−0.0081 (17)	−0.0011 (13)	0.0004 (13)
C16	0.065 (2)	0.0583 (19)	0.0498 (14)	−0.0058 (18)	0.0005 (13)	−0.0007 (13)
C17	0.064 (2)	0.087 (3)	0.0703 (18)	−0.003 (2)	0.0061 (15)	−0.0099 (18)
C18	0.073 (3)	0.082 (3)	0.0789 (19)	−0.019 (2)	0.0095 (17)	−0.0024 (19)
C19	0.088 (3)	0.069 (2)	0.0620 (17)	−0.013 (2)	0.0050 (16)	0.0052 (15)
C20	0.088 (2)	0.0548 (19)	0.0637 (16)	−0.0058 (18)	−0.0081 (16)	0.0051 (14)
N1	0.0685 (18)	0.0597 (16)	0.0633 (13)	−0.0001 (15)	0.0019 (12)	0.0000 (12)
N2	0.0722 (18)	0.0584 (16)	0.0741 (15)	−0.0010 (15)	0.0036 (13)	0.0116 (13)
O4	0.118 (2)	0.0554 (13)	0.0679 (12)	−0.0034 (14)	−0.0144 (13)	0.0085 (10)
O5	0.0718 (17)	0.113 (2)	0.0909 (16)	0.0031 (16)	0.0009 (13)	0.0184 (15)

C1—C6	1.397 (4)	C13—C14	1.386 (5)
C1—C2	1.386 (4)	C13—H13	0.9300
C1—C8	1.508 (4)	C14—H14	0.9300
C2—C3	1.379 (5)	C15—C19	1.361 (4)
C2—H2	0.9300	C15—C16	1.423 (4)
C3—C4	1.356 (5)	C15—C20	1.491 (5)
C3—H3	0.9300	C16—N2	1.333 (4)
C4—C5	1.382 (5)	C16—N1	1.340 (4)
C4—H4	0.9300	C17—N1	1.353 (4)
C5—C6	1.383 (4)	C17—C18	1.353 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.511 (4)	C18—C19	1.393 (5)
C7—O1	1.252 (4)	C18—H18	0.9300
C7—O2	1.252 (3)	C19—H19	0.9300
C8—O3	1.212 (3)	C20—O4	1.417 (4)
C8—C9	1.490 (4)	C20—H20A	0.9700
C9—C14	1.382 (4)	C20—H20B	0.9700
C9—C10	1.385 (4)	N1—H1	0.8600
C10—C11	1.373 (4)	N2—H2A	0.8600
C10—H10	0.9300	N2—H2B	0.8600
C11—C12	1.369 (5)	O4—H4A	0.859 (19)
C11—H11	0.9300	O5—H5A	0.858 (18)
C12—C13	1.378 (5)	O5—H5B	0.858 (19)
C12—H12	0.9300
C6—C1—C2	119.8 (3)	C12—C13—C14	119.9 (3)
C6—C1—C8	121.8 (3)	C12—C13—H13	120.0
C2—C1—C8	118.3 (3)	C14—C13—H13	120.0
C3—C2—C1	120.1 (3)	C9—C14—C13	119.8 (3)
C3—C2—H2	120.0	C9—C14—H14	120.1
C1—C2—H2	120.0	C13—C14—H14	120.1
C4—C3—C2	120.4 (3)	C19—C15—C16	117.2 (3)
C4—C3—H3	119.8	C19—C15—C20	123.7 (3)
C2—C3—H3	119.8	C16—C15—C20	119.1 (3)
C3—C4—C5	120.1 (3)	N2—C16—N1	118.1 (3)
C3—C4—H4	119.9	N2—C16—C15	123.1 (3)
C5—C4—H4	119.9	N1—C16—C15	118.8 (3)
C4—C5—C6	120.9 (3)	N1—C17—C18	120.9 (3)
C4—C5—H5	119.6	N1—C17—H17	119.5
C6—C5—H5	119.6	C18—C17—H17	119.5
C1—C6—C5	118.6 (3)	C17—C18—C19	117.5 (4)
C1—C6—C7	119.6 (3)	C17—C18—H18	121.2
C5—C6—C7	121.6 (3)	C19—C18—H18	121.2
O1—C7—O2	124.8 (3)	C15—C19—C18	122.9 (3)
O1—C7—C6	118.8 (3)	C15—C19—H19	118.5
O2—C7—C6	116.3 (3)	C18—C19—H19	118.5
O3—C8—C9	121.2 (3)	O4—C20—C15	113.8 (3)
O3—C8—C1	121.0 (3)	O4—C20—H20A	108.8
C9—C8—C1	117.7 (2)	C15—C20—H20A	108.8
C14—C9—C10	119.3 (3)	O4—C20—H20B	108.8
C14—C9—C8	120.5 (3)	C15—C20—H20B	108.8
C10—C9—C8	120.0 (3)	H20A—C20—H20B	107.7
C11—C10—C9	120.7 (3)	C16—N1—C17	122.6 (3)
C11—C10—H10	119.6	C16—N1—H1	118.7
C9—C10—H10	119.6	C17—N1—H1	118.7
C12—C11—C10	119.7 (3)	C16—N2—H2A	120.0
C12—C11—H11	120.1	C16—N2—H2B	120.0
C10—C11—H11	120.1	H2A—N2—H2B	120.0
C11—C12—C13	120.5 (3)	C20—O4—H4A	106 (3)
C11—C12—H12	119.8	H5A—O5—H5B	106 (3)
C13—C12—H12	119.8
C6—C1—C2—C3	0.9 (4)	C1—C8—C9—C10	155.1 (3)
C8—C1—C2—C3	−175.8 (3)	C14—C9—C10—C11	−1.1 (5)
C1—C2—C3—C4	0.5 (5)	C8—C9—C10—C11	174.4 (3)
C2—C3—C4—C5	−1.0 (5)	C9—C10—C11—C12	−0.4 (5)
C3—C4—C5—C6	0.1 (5)	C10—C11—C12—C13	0.8 (5)
C2—C1—C6—C5	−1.7 (4)	C11—C12—C13—C14	0.3 (5)
C8—C1—C6—C5	174.8 (2)	C10—C9—C14—C13	2.2 (5)
C2—C1—C6—C7	172.4 (3)	C8—C9—C14—C13	−173.3 (3)
C8—C1—C6—C7	−11.0 (4)	C12—C13—C14—C9	−1.9 (5)
C4—C5—C6—C1	1.2 (4)	C19—C15—C16—N2	178.5 (3)
C4—C5—C6—C7	−172.8 (3)	C20—C15—C16—N2	−0.4 (4)
C1—C6—C7—O1	155.1 (3)	C19—C15—C16—N1	−1.8 (4)
C5—C6—C7—O1	−30.9 (4)	C20—C15—C16—N1	179.4 (2)
C1—C6—C7—O2	−26.5 (4)	N1—C17—C18—C19	−0.7 (5)
C5—C6—C7—O2	147.4 (3)	C16—C15—C19—C18	1.7 (4)
C6—C1—C8—O3	121.8 (3)	C20—C15—C19—C18	−179.6 (3)
C2—C1—C8—O3	−61.6 (4)	C17—C18—C19—C15	−0.5 (5)
C6—C1—C8—C9	−63.1 (3)	C19—C15—C20—O4	5.2 (4)
C2—C1—C8—C9	113.5 (3)	C16—C15—C20—O4	−176.1 (2)
O3—C8—C9—C14	145.7 (3)	N2—C16—N1—C17	−179.5 (2)
C1—C8—C9—C14	−29.5 (4)	C15—C16—N1—C17	0.8 (4)
O3—C8—C9—C10	−29.8 (4)	C18—C17—N1—C16	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.93	2.775 (3)	167
N1—H1···O2i	0.86	2.62	3.303 (3)	137
N2—H2A···O2i	0.86	2.04	2.845 (3)	156
N2—H2B···O5ii	0.86	2.11	2.942 (4)	162
O4—H4A···O2iii	0.86 (2)	1.92 (2)	2.765 (3)	168 (4)
O5—H5A···O4	0.86 (2)	1.96 (2)	2.807 (3)	167 (4)
O5—H5B···O1	0.86 (2)	2.28 (4)	2.964 (4)	136 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.93	2.775 (3)	167
N1—H1⋯O2i	0.86	2.62	3.303 (3)	137
N2—H2A⋯O2i	0.86	2.04	2.845 (3)	156
N2—H2B⋯O5ii	0.86	2.11	2.942 (4)	162
O4—H4A⋯O2iii	0.86 (2)	1.92 (2)	2.765 (3)	168 (4)
O5—H5A⋯O4	0.86 (2)	1.96 (2)	2.807 (3)	167 (4)
O5—H5B⋯O1	0.86 (2)	2.28 (4)	2.964 (4)	136 (4)

Symmetry codes: (i) ; (ii) ; (iii) .