Acridin-10-ium 6-carb-oxy-pyridine-2-carboxyl-ate.

The title compound, C(13)H(10)N(+)·C(7)H(4)NO(4) (-), consists of a protonated acridinium cation and a 6-carb-oxy-pyridine-2-carboxyl-ate monoanion. The carboxyl-ate group of the anion appears to be delocalized on the basis of the nearly equivalent C-O bond lengths. In the crystal, the anions are connected by strong O-H⋯O hydrogen bonds, forming chains along the b axis. The acridinium cations are linked to the anionic chains by strong N-H⋯O hydrogen bonds between the carboxyl-ate group of the anion and the N-H group of the cation. Along the b axis, successive chains stack in opposite directions. Weak inter-molecular C-H⋯O hydrogen bonds further stabilize the crystal structure.

Related literature

For related crystal structures of acridinium compounds with carboxyl­ate, see: Shaameri et al. (2001 ▶); Derikvand et al. (2009 ▶); Attar Gharamaleki et al. (2010 ▶).

Experimental

Crystal data

C13H10N+·n class="Chemical">C7H4NO4 −

M = 346.33

Monoclinic,

a = 16.6817 (8) Å

b = 8.2872 (4) Å

c = 23.7289 (12) Å

β = 105.582 (1)°

V = 3159.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.29 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.884, T max = 1.000

11354 measured reflections

3894 independent reflections

2198 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.06

3894 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053578/su2350sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053578/su2350Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053578/su2350Isup3.cml

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

C13H10N+·C7H4NO4−	F(000) = 1440
Mr = 346.33	Dx = 1.456 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3018 reflections
a = 16.6817 (8) Å	θ = 2.5–27.8°
b = 8.2872 (4) Å	µ = 0.10 mm−1
c = 23.7289 (12) Å	T = 200 K
β = 105.582 (1)°	Block, yellow
V = 3159.8 (3) Å3	0.29 × 0.18 × 0.17 mm
Z = 8

Bruker SMART 1000 CCD diffractometer	3894 independent reflections
Radiation source: fine-focus sealed tube	2198 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −22→19
Tmin = 0.884, Tmax = 1.000	k = −10→11
11354 measured reflections	l = −29→31

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.8669P] where P = (Fo2 + 2Fc2)/3
3894 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 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
N1	−0.04881 (10)	0.2361 (2)	−0.00985 (7)	0.0305 (4)
H1N	−0.1001	0.2338	−0.0367	0.046*
C1	−0.04063 (12)	0.1529 (2)	0.04054 (9)	0.0300 (5)
C2	−0.11101 (13)	0.0861 (3)	0.05417 (10)	0.0369 (5)
H2	−0.1648	0.0986	0.0280	0.044*
C3	−0.10107 (14)	0.0039 (3)	0.10497 (10)	0.0410 (6)
H3	−0.1486	−0.0397	0.1143	0.049*
C4	−0.02137 (14)	−0.0185 (3)	0.14456 (10)	0.0408 (6)
H4	−0.0161	−0.0766	0.1799	0.049*
C5	0.04717 (14)	0.0427 (3)	0.13213 (9)	0.0366 (5)
H5	0.1005	0.0258	0.1584	0.044*
C6	0.03965 (13)	0.1322 (3)	0.07986 (9)	0.0308 (5)
C7	0.10755 (13)	0.2029 (3)	0.06581 (9)	0.0338 (5)
H7	0.1617	0.1884	0.0912	0.041*
C8	0.09735 (12)	0.2943 (3)	0.01523 (9)	0.0317 (5)
C9	0.16393 (14)	0.3735 (3)	−0.00016 (10)	0.0413 (6)
H9	0.2183	0.3690	0.0257	0.050*
C10	0.15110 (15)	0.4556 (3)	−0.05128 (11)	0.0446 (6)
H10	0.1965	0.5060	−0.0613	0.054*
C11	0.07003 (14)	0.4662 (3)	−0.08980 (10)	0.0408 (6)
H11	0.0618	0.5243	−0.1254	0.049*
C12	0.00364 (14)	0.3949 (3)	−0.07683 (9)	0.0344 (5)
H12	−0.0504	0.4037	−0.1029	0.041*
C13	0.01634 (12)	0.3078 (2)	−0.02393 (9)	0.0294 (5)
O1	0.24957 (9)	0.82325 (18)	0.32785 (7)	0.0433 (4)
H1O	0.2533	0.9241	0.3311	0.065*
O2	0.13288 (10)	0.87006 (19)	0.25747 (7)	0.0475 (5)
O3	0.30738 (9)	0.32253 (19)	0.41697 (7)	0.0431 (4)
O4	0.29134 (9)	0.11156 (19)	0.35743 (7)	0.0462 (5)
N2	0.22360 (10)	0.5100 (2)	0.32603 (7)	0.0295 (4)
C14	0.17072 (12)	0.5985 (3)	0.28554 (9)	0.0295 (5)
C15	0.10598 (13)	0.5332 (3)	0.24202 (10)	0.0369 (5)
H15	0.0686	0.6007	0.2148	0.044*
C16	0.09746 (14)	0.3678 (3)	0.23931 (10)	0.0407 (6)
H16	0.0540	0.3192	0.2099	0.049*
C17	0.15273 (13)	0.2735 (3)	0.27968 (9)	0.0346 (5)
H17	0.1489	0.1591	0.2779	0.041*
C18	0.21413 (12)	0.3490 (2)	0.32294 (9)	0.0284 (5)
C19	0.18181 (13)	0.7786 (3)	0.28826 (9)	0.0315 (5)
C20	0.27569 (12)	0.2525 (3)	0.36928 (10)	0.0317 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0284 (9)	0.0307 (10)	0.0287 (10)	−0.0019 (8)	0.0014 (8)	−0.0006 (8)
C1	0.0333 (11)	0.0281 (12)	0.0270 (11)	0.0005 (9)	0.0054 (9)	−0.0018 (9)
C2	0.0321 (12)	0.0428 (14)	0.0339 (13)	−0.0032 (10)	0.0056 (10)	0.0001 (11)
C3	0.0422 (13)	0.0437 (15)	0.0396 (14)	−0.0047 (11)	0.0153 (11)	0.0029 (11)
C4	0.0491 (14)	0.0400 (14)	0.0331 (13)	0.0023 (11)	0.0106 (11)	0.0059 (10)
C5	0.0410 (13)	0.0360 (13)	0.0290 (12)	0.0066 (10)	0.0030 (10)	0.0012 (10)
C6	0.0328 (11)	0.0285 (12)	0.0289 (12)	0.0023 (9)	0.0048 (9)	−0.0046 (9)
C7	0.0286 (11)	0.0379 (13)	0.0300 (12)	0.0006 (10)	−0.0005 (9)	−0.0045 (10)
C8	0.0315 (11)	0.0307 (12)	0.0313 (12)	−0.0033 (9)	0.0055 (9)	−0.0052 (10)
C9	0.0309 (12)	0.0485 (15)	0.0416 (14)	−0.0053 (11)	0.0045 (10)	−0.0037 (12)
C10	0.0423 (14)	0.0479 (16)	0.0468 (15)	−0.0110 (12)	0.0173 (11)	−0.0029 (12)
C11	0.0490 (14)	0.0371 (14)	0.0369 (14)	−0.0043 (11)	0.0124 (11)	0.0029 (11)
C12	0.0377 (12)	0.0328 (13)	0.0303 (12)	−0.0004 (10)	0.0047 (10)	−0.0012 (10)
C13	0.0294 (11)	0.0262 (12)	0.0319 (12)	−0.0030 (9)	0.0072 (9)	−0.0048 (9)
O1	0.0412 (9)	0.0265 (9)	0.0531 (11)	0.0000 (7)	−0.0029 (8)	0.0003 (7)
O2	0.0533 (10)	0.0325 (9)	0.0460 (10)	0.0081 (8)	−0.0049 (8)	0.0074 (8)
O3	0.0454 (9)	0.0406 (10)	0.0344 (9)	0.0111 (8)	−0.0047 (7)	−0.0041 (8)
O4	0.0396 (9)	0.0277 (9)	0.0617 (12)	0.0043 (7)	−0.0029 (8)	−0.0070 (8)
N2	0.0277 (9)	0.0319 (10)	0.0283 (10)	0.0035 (8)	0.0063 (7)	0.0020 (8)
C14	0.0302 (11)	0.0292 (12)	0.0292 (12)	0.0011 (9)	0.0082 (9)	0.0007 (9)
C15	0.0375 (12)	0.0381 (14)	0.0305 (12)	0.0037 (10)	0.0010 (10)	0.0012 (10)
C16	0.0375 (12)	0.0389 (14)	0.0375 (14)	−0.0019 (11)	−0.0040 (10)	−0.0047 (11)
C17	0.0349 (12)	0.0292 (12)	0.0354 (13)	−0.0003 (10)	0.0021 (10)	−0.0034 (10)
C18	0.0276 (10)	0.0262 (12)	0.0313 (12)	0.0005 (9)	0.0077 (9)	−0.0008 (9)
C19	0.0330 (11)	0.0324 (12)	0.0285 (12)	0.0009 (10)	0.0071 (9)	0.0023 (10)
C20	0.0270 (11)	0.0295 (13)	0.0371 (13)	0.0002 (9)	0.0057 (10)	−0.0005 (10)

N1—C1	1.355 (3)	C10—H10	0.9500
N1—C13	1.357 (3)	C11—C12	1.361 (3)
N1—H1N	0.9200	C11—H11	0.9500
C1—C2	1.412 (3)	C12—C13	1.414 (3)
C1—C6	1.422 (3)	C12—H12	0.9500
C2—C3	1.355 (3)	O1—C19	1.314 (2)
C2—H2	0.9500	O1—H1O	0.8400
C3—C4	1.419 (3)	O2—C19	1.206 (2)
C3—H3	0.9500	O3—C20	1.255 (2)
C4—C5	1.354 (3)	O4—C20	1.246 (3)
C4—H4	0.9500	N2—C14	1.335 (3)
C5—C6	1.421 (3)	N2—C18	1.344 (3)
C5—H5	0.9500	C14—C15	1.388 (3)
C6—C7	1.393 (3)	C14—C19	1.503 (3)
C7—C8	1.390 (3)	C15—C16	1.378 (3)
C7—H7	0.9500	C15—H15	0.9500
C8—C9	1.420 (3)	C16—C17	1.380 (3)
C8—C13	1.424 (3)	C16—H16	0.9500
C9—C10	1.357 (3)	C17—C18	1.389 (3)
C9—H9	0.9500	C17—H17	0.9500
C10—C11	1.417 (3)	C18—C20	1.515 (3)
C1—N1—C13	122.86 (17)	C12—C11—C10	121.4 (2)
C1—N1—H1N	117.1	C12—C11—H11	119.3
C13—N1—H1N	119.7	C10—C11—H11	119.3
N1—C1—C2	120.59 (18)	C11—C12—C13	119.0 (2)
N1—C1—C6	119.62 (19)	C11—C12—H12	120.5
C2—C1—C6	119.8 (2)	C13—C12—H12	120.5
C3—C2—C1	119.3 (2)	N1—C13—C12	120.22 (18)
C3—C2—H2	120.3	N1—C13—C8	119.18 (19)
C1—C2—H2	120.3	C12—C13—C8	120.60 (19)
C2—C3—C4	121.6 (2)	C19—O1—H1O	112.0
C2—C3—H3	119.2	C14—N2—C18	117.44 (18)
C4—C3—H3	119.2	N2—C14—C15	123.6 (2)
C5—C4—C3	120.2 (2)	N2—C14—C19	117.66 (19)
C5—C4—H4	119.9	C15—C14—C19	118.77 (19)
C3—C4—H4	119.9	C16—C15—C14	118.2 (2)
C4—C5—C6	120.3 (2)	C16—C15—H15	120.9
C4—C5—H5	119.9	C14—C15—H15	120.9
C6—C5—H5	119.9	C15—C16—C17	119.3 (2)
C7—C6—C5	122.78 (19)	C15—C16—H16	120.3
C7—C6—C1	118.4 (2)	C17—C16—H16	120.3
C5—C6—C1	118.8 (2)	C16—C17—C18	118.7 (2)
C8—C7—C6	121.12 (19)	C16—C17—H17	120.6
C8—C7—H7	119.4	C18—C17—H17	120.6
C6—C7—H7	119.4	N2—C18—C17	122.70 (19)
C7—C8—C9	123.4 (2)	N2—C18—C20	115.95 (18)
C7—C8—C13	118.73 (19)	C17—C18—C20	121.34 (19)
C9—C8—C13	117.8 (2)	O2—C19—O1	124.6 (2)
C10—C9—C8	121.0 (2)	O2—C19—C14	122.9 (2)
C10—C9—H9	119.5	O1—C19—C14	112.50 (18)
C8—C9—H9	119.5	O4—C20—O3	125.0 (2)
C9—C10—C11	120.1 (2)	O4—C20—C18	118.25 (19)
C9—C10—H10	119.9	O3—C20—C18	116.73 (19)
C11—C10—H10	119.9
C13—N1—C1—C2	177.4 (2)	C11—C12—C13—N1	179.8 (2)
C13—N1—C1—C6	−2.9 (3)	C11—C12—C13—C8	−0.1 (3)
N1—C1—C2—C3	−179.8 (2)	C7—C8—C13—N1	2.3 (3)
C6—C1—C2—C3	0.5 (3)	C9—C8—C13—N1	−178.68 (19)
C1—C2—C3—C4	−0.8 (4)	C7—C8—C13—C12	−177.8 (2)
C2—C3—C4—C5	0.0 (4)	C9—C8—C13—C12	1.2 (3)
C3—C4—C5—C6	1.1 (4)	C18—N2—C14—C15	1.8 (3)
C4—C5—C6—C7	177.6 (2)	C18—N2—C14—C19	−179.12 (18)
C4—C5—C6—C1	−1.4 (3)	N2—C14—C15—C16	−2.2 (3)
N1—C1—C6—C7	1.8 (3)	C19—C14—C15—C16	178.8 (2)
C2—C1—C6—C7	−178.5 (2)	C14—C15—C16—C17	0.3 (4)
N1—C1—C6—C5	−179.16 (19)	C15—C16—C17—C18	1.7 (3)
C2—C1—C6—C5	0.6 (3)	C14—N2—C18—C17	0.4 (3)
C5—C6—C7—C8	−177.7 (2)	C14—N2—C18—C20	179.50 (18)
C1—C6—C7—C8	1.2 (3)	C16—C17—C18—N2	−2.2 (3)
C6—C7—C8—C9	177.8 (2)	C16—C17—C18—C20	178.8 (2)
C6—C7—C8—C13	−3.2 (3)	N2—C14—C19—O2	−172.6 (2)
C7—C8—C9—C10	177.2 (2)	C15—C14—C19—O2	6.5 (3)
C13—C8—C9—C10	−1.8 (3)	N2—C14—C19—O1	6.8 (3)
C8—C9—C10—C11	1.3 (4)	C15—C14—C19—O1	−174.07 (19)
C9—C10—C11—C12	−0.2 (4)	N2—C18—C20—O4	−153.4 (2)
C10—C11—C12—C13	−0.4 (3)	C17—C18—C20—O4	25.7 (3)
C1—N1—C13—C12	−179.1 (2)	N2—C18—C20—O3	26.3 (3)
C1—N1—C13—C8	0.8 (3)	C17—C18—C20—O3	−154.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.92	1.70	2.602 (2)	165.
O1—H1O···O4ii	0.84	1.73	2.535 (2)	160.
C7—H7···O1iii	0.95	2.37	3.132 (2)	137.
C10—H10···O3iv	0.95	2.49	3.435 (3)	171.
C12—H12···O4i	0.95	2.56	3.466 (3)	160.
C17—H17···O2v	0.95	2.44	3.387 (3)	171.

O1—C19	1.314 (2)
O2—C19	1.206 (2)
O3—C20	1.255 (2)
O4—C20	1.246 (3)

O2—C19—O1	124.6 (2)
O4—C20—O3	125.0 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.92	1.70	2.602 (2)	165
O1—H1O⋯O4ii	0.84	1.73	2.535 (2)	160
C7—H7⋯O1iii	0.95	2.37	3.132 (2)	137
C10—H10⋯O3iv	0.95	2.49	3.435 (3)	171
C12—H12⋯O4i	0.95	2.56	3.466 (3)	160
C17—H17⋯O2v	0.95	2.44	3.387 (3)	171

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