Acridinium 3,5-dicarboxy-benzoate monohydrate.

The title compound, C(13)H(10)N(+)·C(9)H(5)O(6) (-)·H(2)O, exhibits a wide range of non-covalent inter-actions, such as O-H⋯O and N-H⋯O hydrogen bonds, π-π stacking [centroid-centroid distances = 3.562 (8) and 3.872 (8) Å] and ion pairing, connecting the various components into a supra-molecular structure.

Related literature

For background to proton transfer compounds, see: Aghabozorg et al. (2008 ▶); (Tabatabaee et al. 2009 ▶). For related structures, see: Zadykowicz, Trzybiński et al. (2009 ▶); Zadykowicz, Krzymiński et al. (2009 ▶); Trzybiński et al. (2009 ▶).

Experimental

Crystal data

C13H10N+·C9H5O6 −·H2O

M = 407.37

Triclinic,

a = 6.8554 (4) Å

b = 9.6930 (6) Å

c = 14.8916 (10) Å

α = 103.6870 (10)°

β = 101.4240 (10)°

γ = 103.3100 (10)°

V = 901.62 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.971, T max = 0.980

9138 measured reflections

4275 independent reflections

3659 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.01

4275 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015529/pv2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015529/pv2154Isup2.hkl

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

C13H10N+·C9H5O6−·H2O	Z = 2
Mr = 407.37	F(000) = 424
Triclinic, P1	Dx = 1.501 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8554 (4) Å	Cell parameters from 5147 reflections
b = 9.6930 (6) Å	θ = 2.3–30.0°
c = 14.8916 (10) Å	µ = 0.11 mm−1
α = 103.687 (1)°	T = 120 K
β = 101.424 (1)°	Prism, brown
γ = 103.310 (1)°	0.25 × 0.20 × 0.15 mm
V = 901.62 (10) Å3

Bruker SMART 1000 CCD area-detector diffractometer	4275 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −9→9
Tmin = 0.971, Tmax = 0.980	k = −12→12
9138 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: mixed
wR(F2) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.08P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3
4275 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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
O1	0.53402 (13)	0.57945 (10)	0.27673 (6)	0.0210 (2)
O2	0.84684 (14)	0.54218 (10)	0.30488 (6)	0.0236 (2)
O3	0.76596 (15)	0.03275 (10)	−0.06853 (6)	0.0239 (2)
H3O	0.8501	−0.0268	−0.0766	0.029*
O4	0.96967 (16)	0.12545 (11)	0.08194 (7)	0.0283 (2)
O5	0.07764 (15)	0.36662 (11)	−0.05679 (7)	0.0247 (2)
H5O	−0.0207	0.3674	−0.1061	0.030*
O6	0.16639 (16)	0.20983 (12)	−0.16763 (7)	0.0287 (2)
O7	0.16191 (15)	0.62966 (12)	0.21813 (7)	0.0295 (2)
H7B	0.2751	0.6054	0.2375	0.044*
H7C	0.0765	0.5958	0.2499	0.044*
N1	0.68310 (16)	0.81261 (11)	0.43083 (7)	0.0179 (2)
H1N	0.6431	0.7352	0.3794	0.022*
C1	0.8239 (2)	0.88639 (15)	0.69373 (9)	0.0240 (3)
H1A	0.8669	0.9668	0.7510	0.029*
C2	0.7957 (2)	0.74436 (16)	0.69839 (9)	0.0253 (3)
H2A	0.8134	0.7262	0.7590	0.030*
C3	0.7401 (2)	0.62373 (15)	0.61357 (10)	0.0241 (3)
H3A	0.7253	0.5261	0.6184	0.029*
C4	0.70732 (19)	0.64520 (14)	0.52498 (9)	0.0211 (3)
H4A	0.6729	0.5637	0.4688	0.025*
C4A	0.72531 (18)	0.79041 (13)	0.51809 (9)	0.0181 (2)
C5	0.6491 (2)	0.96360 (15)	0.32571 (9)	0.0225 (3)
H5A	0.6004	0.8784	0.2711	0.027*
C6	0.6712 (2)	1.10214 (16)	0.31508 (10)	0.0264 (3)
H6A	0.6369	1.1125	0.2525	0.032*
C7	0.7447 (2)	1.23140 (15)	0.39604 (11)	0.0266 (3)
H7A	0.7607	1.3267	0.3869	0.032*
C8	0.7923 (2)	1.21908 (14)	0.48666 (10)	0.0246 (3)
H8A	0.8408	1.3058	0.5402	0.029*
C8A	0.76947 (18)	1.07638 (13)	0.50154 (9)	0.0197 (3)
C9	0.81271 (19)	1.05643 (14)	0.59263 (9)	0.0214 (3)
H9A	0.8587	1.1402	0.6481	0.026*
C9A	0.78877 (18)	0.91388 (14)	0.60267 (9)	0.0197 (3)
C10A	0.69968 (19)	0.94890 (14)	0.41914 (9)	0.0188 (2)
C10	0.60515 (18)	0.40594 (13)	0.15426 (8)	0.0175 (2)
C11	0.73036 (19)	0.31547 (13)	0.13153 (9)	0.0186 (2)
H11A	0.8505	0.3220	0.1787	0.022*
C12	0.68132 (19)	0.21555 (13)	0.04031 (9)	0.0180 (2)
C13	0.50674 (19)	0.20648 (13)	−0.02982 (9)	0.0185 (2)
H13A	0.4746	0.1400	−0.0925	0.022*
C14	0.37953 (18)	0.29568 (13)	−0.00735 (8)	0.0179 (2)
C15	0.42717 (18)	0.39407 (13)	0.08446 (9)	0.0180 (2)
H15A	0.3385	0.4532	0.0996	0.022*
C16	0.66843 (19)	0.51724 (13)	0.25273 (8)	0.0182 (2)
C17	0.8191 (2)	0.12108 (14)	0.01994 (9)	0.0197 (2)
C18	0.19722 (19)	0.28509 (14)	−0.08559 (9)	0.0197 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0199 (4)	0.0232 (4)	0.0190 (4)	0.0101 (3)	0.0046 (3)	0.0011 (3)
O2	0.0210 (4)	0.0291 (5)	0.0181 (4)	0.0119 (4)	0.0008 (3)	0.0015 (4)
O3	0.0269 (5)	0.0273 (5)	0.0181 (4)	0.0167 (4)	0.0040 (4)	0.0010 (4)
O4	0.0307 (5)	0.0337 (5)	0.0201 (5)	0.0215 (4)	0.0013 (4)	0.0003 (4)
O5	0.0235 (5)	0.0319 (5)	0.0203 (4)	0.0166 (4)	0.0029 (4)	0.0047 (4)
O6	0.0282 (5)	0.0354 (5)	0.0193 (5)	0.0166 (4)	0.0011 (4)	−0.0005 (4)
O7	0.0228 (5)	0.0415 (6)	0.0279 (5)	0.0168 (4)	0.0044 (4)	0.0119 (4)
N1	0.0181 (5)	0.0184 (5)	0.0162 (5)	0.0060 (4)	0.0052 (4)	0.0019 (4)
C1	0.0213 (6)	0.0289 (6)	0.0169 (6)	0.0050 (5)	0.0031 (5)	0.0019 (5)
C2	0.0211 (6)	0.0337 (7)	0.0192 (6)	0.0067 (5)	0.0030 (5)	0.0080 (5)
C3	0.0214 (6)	0.0248 (6)	0.0252 (6)	0.0060 (5)	0.0040 (5)	0.0083 (5)
C4	0.0197 (6)	0.0205 (6)	0.0204 (6)	0.0048 (4)	0.0042 (5)	0.0029 (5)
C4A	0.0138 (5)	0.0211 (6)	0.0180 (6)	0.0046 (4)	0.0047 (4)	0.0034 (4)
C5	0.0237 (6)	0.0256 (6)	0.0202 (6)	0.0102 (5)	0.0080 (5)	0.0059 (5)
C6	0.0262 (7)	0.0314 (7)	0.0287 (7)	0.0137 (5)	0.0109 (5)	0.0142 (6)
C7	0.0233 (6)	0.0223 (6)	0.0388 (8)	0.0098 (5)	0.0121 (6)	0.0114 (6)
C8	0.0209 (6)	0.0197 (6)	0.0324 (7)	0.0076 (5)	0.0079 (5)	0.0041 (5)
C8A	0.0147 (5)	0.0193 (6)	0.0242 (6)	0.0061 (4)	0.0065 (4)	0.0028 (5)
C9	0.0187 (6)	0.0203 (6)	0.0205 (6)	0.0047 (4)	0.0047 (5)	−0.0012 (5)
C9A	0.0162 (6)	0.0217 (6)	0.0186 (6)	0.0042 (4)	0.0049 (4)	0.0022 (5)
C10A	0.0166 (5)	0.0207 (6)	0.0200 (6)	0.0070 (4)	0.0068 (4)	0.0048 (5)
C10	0.0188 (6)	0.0189 (5)	0.0160 (5)	0.0079 (4)	0.0049 (4)	0.0045 (4)
C11	0.0191 (6)	0.0195 (6)	0.0175 (5)	0.0086 (4)	0.0037 (4)	0.0042 (4)
C12	0.0197 (6)	0.0185 (5)	0.0182 (6)	0.0096 (4)	0.0065 (4)	0.0050 (4)
C13	0.0205 (6)	0.0195 (5)	0.0162 (5)	0.0085 (4)	0.0051 (4)	0.0036 (4)
C14	0.0187 (5)	0.0196 (6)	0.0165 (5)	0.0082 (4)	0.0047 (4)	0.0049 (4)
C15	0.0180 (6)	0.0189 (5)	0.0177 (5)	0.0076 (4)	0.0054 (4)	0.0040 (4)
C16	0.0201 (6)	0.0198 (5)	0.0170 (5)	0.0086 (4)	0.0055 (4)	0.0062 (4)
C17	0.0222 (6)	0.0202 (6)	0.0181 (6)	0.0103 (5)	0.0054 (5)	0.0040 (4)
C18	0.0191 (6)	0.0207 (6)	0.0199 (6)	0.0085 (4)	0.0045 (4)	0.0053 (4)

O1—C16	1.2747 (15)	C5—C10A	1.4148 (17)
O2—C16	1.2474 (15)	C5—H5A	0.9500
O3—C17	1.3167 (15)	C6—C7	1.425 (2)
O3—H3O	0.9102	C6—H6A	0.9500
O4—C17	1.2261 (16)	C7—C8	1.364 (2)
O5—C18	1.3258 (15)	C7—H7A	0.9500
O5—H5O	0.8953	C8—C8A	1.4303 (18)
O6—C18	1.2143 (16)	C8—H8A	0.9500
O7—H7B	0.8764	C8A—C9	1.3988 (18)
O7—H7C	0.8773	C8A—C10A	1.4280 (17)
N1—C4A	1.3529 (16)	C9—C9A	1.4006 (18)
N1—C10A	1.3550 (16)	C9—H9A	0.9500
N1—H1N	0.8800	C10—C11	1.3934 (16)
C1—C2	1.366 (2)	C10—C15	1.3995 (17)
C1—C9A	1.4280 (18)	C10—C16	1.5120 (16)
C1—H1A	0.9500	C11—C12	1.3938 (16)
C2—C3	1.4188 (19)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.3942 (17)
C3—C4	1.3668 (18)	C12—C17	1.4844 (16)
C3—H3A	0.9500	C13—C14	1.3950 (16)
C4—C4A	1.4144 (17)	C13—H13A	0.9500
C4—H4A	0.9500	C14—C15	1.3957 (17)
C4A—C9A	1.4275 (17)	C14—C18	1.4958 (17)
C5—C6	1.3667 (19)	C15—H15A	0.9500
C17—O3—H3O	111.8	C8A—C9—C9A	120.49 (11)
C18—O5—H5O	111.9	C8A—C9—H9A	119.8
H7B—O7—H7C	105.4	C9A—C9—H9A	119.8
C4A—N1—C10A	122.85 (11)	C9—C9A—C4A	118.55 (11)
C4A—N1—H1N	118.6	C9—C9A—C1	122.95 (12)
C10A—N1—H1N	118.6	C4A—C9A—C1	118.50 (12)
C2—C1—C9A	119.94 (12)	N1—C10A—C5	119.81 (11)
C2—C1—H1A	120.0	N1—C10A—C8A	119.46 (11)
C9A—C1—H1A	120.0	C5—C10A—C8A	120.73 (12)
C1—C2—C3	120.64 (12)	C11—C10—C15	119.08 (11)
C1—C2—H2A	119.7	C11—C10—C16	119.12 (10)
C3—C2—H2A	119.7	C15—C10—C16	121.77 (11)
C4—C3—C2	121.31 (12)	C10—C11—C12	120.76 (11)
C4—C3—H3A	119.3	C10—C11—H11A	119.6
C2—C3—H3A	119.3	C12—C11—H11A	119.6
C3—C4—C4A	119.08 (12)	C13—C12—C11	120.05 (11)
C3—C4—H4A	120.5	C13—C12—C17	121.31 (11)
C4A—C4—H4A	120.5	C11—C12—C17	118.63 (11)
N1—C4A—C4	119.84 (11)	C12—C13—C14	119.52 (11)
N1—C4A—C9A	119.77 (11)	C12—C13—H13A	120.2
C4—C4A—C9A	120.39 (11)	C14—C13—H13A	120.2
C6—C5—C10A	119.08 (12)	C13—C14—C15	120.32 (11)
C6—C5—H5A	120.5	C13—C14—C18	117.62 (11)
C10A—C5—H5A	120.5	C15—C14—C18	122.02 (11)
C5—C6—C7	121.30 (13)	C14—C15—C10	120.23 (11)
C5—C6—H6A	119.3	C14—C15—H15A	119.9
C7—C6—H6A	119.3	C10—C15—H15A	119.9
C8—C7—C6	120.37 (12)	O2—C16—O1	124.40 (11)
C8—C7—H7A	119.8	O2—C16—C10	118.44 (11)
C6—C7—H7A	119.8	O1—C16—C10	117.17 (10)
C7—C8—C8A	120.42 (12)	O4—C17—O3	123.27 (11)
C7—C8—H8A	119.8	O4—C17—C12	121.71 (11)
C8A—C8—H8A	119.8	O3—C17—C12	115.01 (10)
C9—C8A—C10A	118.83 (11)	O6—C18—O5	124.18 (11)
C9—C8A—C8	123.08 (12)	O6—C18—C14	122.11 (11)
C10A—C8A—C8	118.09 (12)	O5—C18—C14	113.70 (11)
C9A—C1—C2—C3	2.7 (2)	C8—C8A—C10A—N1	177.85 (10)
C1—C2—C3—C4	−1.9 (2)	C9—C8A—C10A—C5	178.37 (11)
C2—C3—C4—C4A	−1.30 (19)	C8—C8A—C10A—C5	−1.77 (18)
C10A—N1—C4A—C4	−179.17 (11)	C15—C10—C11—C12	0.76 (18)
C10A—N1—C4A—C9A	0.52 (18)	C16—C10—C11—C12	−177.54 (11)
C3—C4—C4A—N1	−176.65 (11)	C10—C11—C12—C13	0.80 (19)
C3—C4—C4A—C9A	3.66 (18)	C10—C11—C12—C17	−179.65 (11)
C10A—C5—C6—C7	0.2 (2)	C11—C12—C13—C14	−1.38 (18)
C5—C6—C7—C8	−0.9 (2)	C17—C12—C13—C14	179.08 (11)
C6—C7—C8—C8A	0.2 (2)	C12—C13—C14—C15	0.41 (18)
C7—C8—C8A—C9	−179.04 (12)	C12—C13—C14—C18	178.41 (11)
C7—C8—C8A—C10A	1.11 (18)	C13—C14—C15—C10	1.15 (18)
C10A—C8A—C9—C9A	0.28 (18)	C18—C14—C15—C10	−176.75 (11)
C8—C8A—C9—C9A	−179.57 (11)	C11—C10—C15—C14	−1.73 (18)
C8A—C9—C9A—C4A	1.79 (18)	C16—C10—C15—C14	176.53 (11)
C8A—C9—C9A—C1	−177.87 (11)	C11—C10—C16—O2	11.75 (17)
N1—C4A—C9A—C9	−2.23 (17)	C15—C10—C16—O2	−166.50 (11)
C4—C4A—C9A—C9	177.46 (11)	C11—C10—C16—O1	−168.22 (11)
N1—C4A—C9A—C1	177.44 (11)	C15—C10—C16—O1	13.52 (17)
C4—C4A—C9A—C1	−2.87 (18)	C13—C12—C17—O4	−177.96 (12)
C2—C1—C9A—C9	179.34 (12)	C11—C12—C17—O4	2.49 (19)
C2—C1—C9A—C4A	−0.32 (19)	C13—C12—C17—O3	1.45 (17)
C4A—N1—C10A—C5	−178.76 (11)	C11—C12—C17—O3	−178.10 (11)
C4A—N1—C10A—C8A	1.62 (18)	C13—C14—C18—O6	−4.89 (18)
C6—C5—C10A—N1	−178.51 (11)	C15—C14—C18—O6	173.07 (12)
C6—C5—C10A—C8A	1.10 (19)	C13—C14—C18—O5	176.13 (11)
C9—C8A—C10A—N1	−2.01 (17)	C15—C14—C18—O5	−5.91 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88	1.76	2.6403 (14)	174
O3—H3O···O4i	0.91	1.73	2.6370 (15)	174
O5—H5O···O7ii	0.90	1.77	2.6412 (14)	165
O7—H7B···O1	0.88	1.85	2.7197 (14)	172
O7—H7C···O2iii	0.88	1.94	2.7989 (15)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.88	1.76	2.6403 (14)	174
O3—H3O⋯O4i	0.91	1.73	2.6370 (15)	174
O5—H5O⋯O7ii	0.90	1.77	2.6412 (14)	165
O7—H7B⋯O1	0.88	1.85	2.7197 (14)	172
O7—H7C⋯O2iii	0.88	1.94	2.7989 (15)	167

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