Acridinium 2-hy-droxy-benzoate.

In the title compound, C(13)H(10)N(+)·C(7)H(5)O(3) (-) or (acrH)(+)(Hsal)(-), the asymmetric unit contains one acridinium cation and one salicylate anion. The acridinium N atom is protonated and the carb-oxy-lic acid group of salicylic acid is deprotonated. Both moieties are planar, with an r.m.s. deviation of 0.0127 Å for the acr cation and 0.0235 ° for the sal anion. They are aligned with a dihedral angle of 71.68 (3)° between them. The crystal structure is stabilized by a network of inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds. C-H⋯π inter-actions are also present.

Related literature

For work on mol­ecular self-association, see: Moghimi et al. (2005 ▶); Eshtiagh-Hosseini, Hassanpoor, Canadillas-Delgado & Mirzaei (2010 ▶); Eshtiagh-Hosseini, Mahjoobizadeh & Mirzaei (2010 ▶). For related structures, see: Gellert & Hsu (1988 ▶); Hemamalini & Fun (2010 ▶); Muthiah et al. (2006 ▶).

Experimental

Crystal data

C13H10N+·C7H5O3 −

M = 317.33

Monoclinic,

a = 7.128 (3) Å

b = 9.472 (3) Å

c = 22.637 (9) Å

β = 91.449 (10)°

V = 1527.9 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.973, T max = 0.991

10437 measured reflections

4488 independent reflections

3161 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.04

4488 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S160053681004345X/bq2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004345X/bq2237Isup2.hkl

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

C13H10N+·C7H5O3−	F(000) = 664
Mr = 317.33	Dx = 1.379 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1285 reflections
a = 7.128 (3) Å	θ = 2–25°
b = 9.472 (3) Å	µ = 0.09 mm−1
c = 22.637 (9) Å	T = 100 K
β = 91.449 (10)°	Prism, light-orange
V = 1527.9 (10) Å3	0.30 × 0.25 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4488 independent reflections
Radiation source: fine-focus sealed tube	3161 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→8
Tmin = 0.973, Tmax = 0.991	k = −12→13
10437 measured reflections	l = −32→25

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2765P] where P = (Fo2 + 2Fc2)/3
4488 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 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
C1	0.74651 (19)	0.32545 (14)	0.35776 (6)	0.0186 (3)
C2	0.73287 (18)	0.43221 (14)	0.30953 (6)	0.0163 (3)
C3	0.89699 (18)	0.48889 (14)	0.28532 (6)	0.0183 (3)
C4	0.8833 (2)	0.59342 (15)	0.24213 (7)	0.0218 (3)
C5	0.7091 (2)	0.63934 (16)	0.22190 (7)	0.0228 (3)
C6	0.5458 (2)	0.58278 (16)	0.24467 (6)	0.0212 (3)
C7	0.5587 (2)	0.47998 (15)	0.28815 (6)	0.0186 (3)
C8	0.70546 (18)	0.32647 (15)	0.01980 (6)	0.0169 (3)
C9	0.76980 (18)	0.40801 (15)	0.06919 (6)	0.0171 (3)
C10	0.81472 (18)	0.54997 (15)	0.06022 (6)	0.0181 (3)
H10	0.8588	0.6041	0.0919	0.022*
C11	0.79458 (18)	0.61143 (15)	0.00465 (6)	0.0173 (3)
C12	0.72746 (17)	0.52574 (15)	−0.04321 (6)	0.0171 (3)
C13	0.70495 (19)	0.58406 (16)	−0.10047 (6)	0.0203 (3)
H13	0.6604	0.5286	−0.1317	0.024*
C14	0.74913 (19)	0.72240 (16)	−0.10951 (7)	0.0236 (3)
H14	0.7341	0.7608	−0.1471	0.028*
C15	0.8176 (2)	0.80885 (16)	−0.06248 (7)	0.0237 (3)
H15	0.8473	0.9028	−0.0697	0.028*
C16	0.84006 (19)	0.75551 (15)	−0.00700 (7)	0.0207 (3)
H16	0.8852	0.8130	0.0235	0.025*
C17	0.78718 (19)	0.34000 (16)	0.12514 (6)	0.0210 (3)
H17	0.8286	0.3909	0.1581	0.025*
C18	0.74345 (19)	0.20068 (16)	0.13068 (7)	0.0228 (3)
H18	0.7544	0.1576	0.1675	0.027*
C19	0.6817 (2)	0.12079 (16)	0.08115 (7)	0.0236 (3)
H19	0.6535	0.0256	0.0858	0.028*
C20	0.66274 (19)	0.18115 (15)	0.02653 (6)	0.0203 (3)
H20	0.6224	0.1277	−0.0058	0.024*
N1	0.68547 (15)	0.38796 (13)	−0.03385 (5)	0.0176 (2)
O1	0.90825 (14)	0.28524 (12)	0.37528 (5)	0.0275 (3)
O2	0.59605 (14)	0.28037 (11)	0.37986 (4)	0.0220 (2)
O3	1.06952 (14)	0.44374 (11)	0.30336 (5)	0.0261 (3)
H1	0.647 (3)	0.324 (2)	−0.0700 (10)	0.053 (6)*
H3	1.044 (3)	0.376 (3)	0.3363 (11)	0.072 (8)*
H4	0.994 (3)	0.634 (2)	0.2274 (8)	0.034 (5)*
H5	0.699 (2)	0.7128 (19)	0.1916 (8)	0.029 (5)*
H6	0.421 (2)	0.6185 (18)	0.2298 (8)	0.028 (5)*
H7	0.447 (2)	0.4414 (16)	0.3052 (7)	0.018 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0232 (7)	0.0150 (6)	0.0173 (6)	0.0020 (5)	−0.0033 (5)	−0.0012 (5)
C2	0.0197 (7)	0.0127 (6)	0.0163 (6)	0.0005 (5)	−0.0011 (5)	−0.0011 (5)
C3	0.0179 (6)	0.0156 (6)	0.0214 (7)	0.0018 (5)	−0.0011 (5)	−0.0039 (5)
C4	0.0241 (7)	0.0174 (7)	0.0241 (8)	−0.0019 (5)	0.0046 (6)	−0.0002 (6)
C5	0.0320 (8)	0.0176 (7)	0.0189 (7)	0.0014 (6)	0.0013 (6)	0.0006 (6)
C6	0.0240 (7)	0.0203 (7)	0.0191 (7)	0.0041 (6)	−0.0035 (5)	0.0001 (5)
C7	0.0194 (7)	0.0177 (7)	0.0185 (7)	0.0007 (5)	−0.0010 (5)	−0.0008 (5)
C8	0.0128 (6)	0.0197 (7)	0.0182 (7)	0.0010 (5)	0.0010 (5)	−0.0011 (5)
C9	0.0135 (6)	0.0209 (7)	0.0168 (7)	0.0014 (5)	−0.0004 (5)	−0.0025 (5)
C10	0.0150 (6)	0.0202 (7)	0.0189 (7)	0.0011 (5)	−0.0016 (5)	−0.0043 (5)
C11	0.0132 (6)	0.0185 (7)	0.0202 (7)	0.0017 (5)	0.0000 (5)	−0.0019 (5)
C12	0.0125 (6)	0.0196 (7)	0.0193 (7)	0.0021 (5)	0.0007 (5)	−0.0009 (5)
C13	0.0179 (7)	0.0253 (7)	0.0177 (7)	0.0016 (5)	−0.0006 (5)	−0.0011 (6)
C14	0.0196 (7)	0.0282 (8)	0.0229 (7)	0.0042 (6)	0.0001 (5)	0.0055 (6)
C15	0.0206 (7)	0.0188 (7)	0.0315 (8)	0.0017 (5)	−0.0001 (6)	0.0028 (6)
C16	0.0177 (7)	0.0183 (7)	0.0262 (8)	0.0008 (5)	−0.0010 (5)	−0.0027 (6)
C17	0.0191 (7)	0.0257 (8)	0.0181 (7)	0.0014 (5)	−0.0007 (5)	−0.0019 (6)
C18	0.0211 (7)	0.0268 (8)	0.0206 (7)	0.0012 (6)	0.0006 (5)	0.0039 (6)
C19	0.0217 (7)	0.0210 (7)	0.0282 (8)	−0.0005 (5)	0.0016 (6)	0.0013 (6)
C20	0.0183 (7)	0.0203 (7)	0.0225 (7)	−0.0019 (5)	0.0003 (5)	−0.0033 (5)
N1	0.0158 (5)	0.0195 (6)	0.0176 (6)	0.0008 (4)	0.0000 (4)	−0.0032 (5)
O1	0.0222 (5)	0.0288 (6)	0.0311 (6)	0.0049 (4)	−0.0045 (4)	0.0095 (5)
O2	0.0231 (5)	0.0232 (5)	0.0197 (5)	−0.0012 (4)	−0.0018 (4)	0.0050 (4)
O3	0.0178 (5)	0.0223 (6)	0.0381 (7)	0.0019 (4)	−0.0009 (4)	0.0022 (5)

C1—O1	1.2681 (17)	C11—C12	1.4268 (19)
C1—O2	1.2688 (17)	C11—C16	1.429 (2)
C1—C2	1.4895 (19)	C12—N1	1.3568 (19)
C2—C7	1.3966 (19)	C12—C13	1.414 (2)
C2—C3	1.4105 (19)	C13—C14	1.364 (2)
C3—O3	1.3551 (17)	C13—H13	0.9300
C3—C4	1.393 (2)	C14—C15	1.420 (2)
C4—C5	1.382 (2)	C14—H14	0.9300
C4—H4	0.943 (18)	C15—C16	1.359 (2)
C5—C6	1.392 (2)	C15—H15	0.9300
C5—H5	0.979 (18)	C16—H16	0.9300
C6—C7	1.386 (2)	C17—C18	1.362 (2)
C6—H6	1.002 (17)	C17—H17	0.9300
C7—H7	0.966 (16)	C18—C19	1.414 (2)
C8—N1	1.3511 (18)	C18—H18	0.9300
C8—C20	1.419 (2)	C19—C20	1.366 (2)
C8—C9	1.4252 (19)	C19—H19	0.9300
C9—C10	1.398 (2)	C20—H20	0.9300
C9—C17	1.424 (2)	N1—H1	1.05 (2)
C10—C11	1.3901 (19)	O3—H3	1.01 (3)
C10—H10	0.9300
O1—C1—O2	123.12 (13)	C12—C11—C16	118.46 (13)
O1—C1—C2	118.37 (12)	N1—C12—C13	119.90 (13)
O2—C1—C2	118.51 (12)	N1—C12—C11	119.98 (12)
C7—C2—C3	118.74 (13)	C13—C12—C11	120.12 (13)
C7—C2—C1	121.00 (12)	C14—C13—C12	119.43 (13)
C3—C2—C1	120.25 (12)	C14—C13—H13	120.3
O3—C3—C4	118.87 (13)	C12—C13—H13	120.3
O3—C3—C2	121.19 (13)	C13—C14—C15	121.19 (14)
C4—C3—C2	119.94 (13)	C13—C14—H14	119.4
C5—C4—C3	120.18 (13)	C15—C14—H14	119.4
C5—C4—H4	120.2 (11)	C16—C15—C14	120.57 (14)
C3—C4—H4	119.6 (11)	C16—C15—H15	119.7
C4—C5—C6	120.56 (14)	C14—C15—H15	119.7
C4—C5—H5	120.5 (10)	C15—C16—C11	120.24 (14)
C6—C5—H5	119.0 (10)	C15—C16—H16	119.9
C7—C6—C5	119.50 (14)	C11—C16—H16	119.9
C7—C6—H6	121.3 (10)	C18—C17—C9	120.34 (13)
C5—C6—H6	119.2 (10)	C18—C17—H17	119.8
C6—C7—C2	121.07 (13)	C9—C17—H17	119.8
C6—C7—H7	120.7 (9)	C17—C18—C19	120.86 (14)
C2—C7—H7	118.2 (9)	C17—C18—H18	119.6
N1—C8—C20	119.78 (12)	C19—C18—H18	119.6
N1—C8—C9	119.74 (13)	C20—C19—C18	121.03 (14)
C20—C8—C9	120.47 (13)	C20—C19—H19	119.5
C10—C9—C17	123.32 (13)	C18—C19—H19	119.5
C10—C9—C8	118.52 (13)	C19—C20—C8	119.13 (13)
C17—C9—C8	118.15 (13)	C19—C20—H20	120.4
C11—C10—C9	121.02 (13)	C8—C20—H20	120.4
C11—C10—H10	119.5	C8—N1—C12	122.44 (12)
C9—C10—H10	119.5	C8—N1—H1	118.3 (12)
C10—C11—C12	118.28 (13)	C12—N1—H1	119.1 (12)
C10—C11—C16	123.25 (13)	C3—O3—H3	104.2 (14)
O1—C1—C2—C7	179.63 (13)	C10—C11—C12—N1	−0.11 (18)
O2—C1—C2—C7	−1.2 (2)	C16—C11—C12—N1	179.08 (12)
O1—C1—C2—C3	−1.5 (2)	C10—C11—C12—C13	−179.99 (12)
O2—C1—C2—C3	177.62 (12)	C16—C11—C12—C13	−0.79 (18)
C7—C2—C3—O3	−178.30 (12)	N1—C12—C13—C14	−179.43 (12)
C1—C2—C3—O3	2.8 (2)	C11—C12—C13—C14	0.44 (19)
C7—C2—C3—C4	1.8 (2)	C12—C13—C14—C15	0.1 (2)
C1—C2—C3—C4	−177.04 (13)	C13—C14—C15—C16	−0.3 (2)
O3—C3—C4—C5	178.54 (13)	C14—C15—C16—C11	−0.1 (2)
C2—C3—C4—C5	−1.6 (2)	C10—C11—C16—C15	179.77 (13)
C3—C4—C5—C6	0.5 (2)	C12—C11—C16—C15	0.62 (19)
C4—C5—C6—C7	0.2 (2)	C10—C9—C17—C18	−179.08 (13)
C5—C6—C7—C2	0.0 (2)	C8—C9—C17—C18	0.14 (19)
C3—C2—C7—C6	−1.1 (2)	C9—C17—C18—C19	0.5 (2)
C1—C2—C7—C6	177.80 (13)	C17—C18—C19—C20	−0.5 (2)
N1—C8—C9—C10	−1.41 (18)	C18—C19—C20—C8	−0.2 (2)
C20—C8—C9—C10	178.42 (12)	N1—C8—C20—C19	−179.31 (12)
N1—C8—C9—C17	179.33 (12)	C9—C8—C20—C19	0.86 (19)
C20—C8—C9—C17	−0.84 (18)	C20—C8—N1—C12	−178.74 (12)
C17—C9—C10—C11	−179.78 (12)	C9—C8—N1—C12	1.09 (19)
C8—C9—C10—C11	1.00 (19)	C13—C12—N1—C8	179.55 (12)
C9—C10—C11—C12	−0.26 (19)	C11—C12—N1—C8	−0.32 (19)
C9—C10—C11—C16	−179.41 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	1.05 (2)	2.49 (2)	3.100 (2)	116.4 (15)
N1—H1···O2i	1.05 (2)	1.55 (2)	2.5887 (19)	174.8 (18)
O3—H3···O1	1.00 (3)	1.58 (2)	2.5141 (19)	153 (2)
C10—H10···O1ii	0.93	2.49	3.294 (2)	145
C18—H18···O3iii	0.93	2.46	3.135 (2)	129
C14—H14···Cg1iv	0.93	2.76	3.644 (2)	159
C17—H17···Cg1	0.93	2.91	3.716 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring of Hsal−.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	1.05 (2)	2.49 (2)	3.100 (2)	116.4 (15)
N1—H1⋯O2i	1.05 (2)	1.55 (2)	2.5887 (19)	174.8 (18)
O3—H3⋯O1	1.00 (3)	1.58 (2)	2.5141 (19)	153 (2)
C10—H10⋯O1ii	0.93	2.49	3.294 (2)	145
C18—H18⋯O3iii	0.93	2.46	3.135 (2)	129
C14—H14⋯Cg1iv	0.93	2.76	3.644 (2)	159
C17—H17⋯Cg1	0.93	2.91	3.716 (2)	146

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