Acridinium 6-carb-oxy-pyridine-2-carboxyl-ate monohydrate.

The title compound, C(13)H(10)N(+)·C(7)H(4)NO(4) (-)·H(2)O or (acrH)(+)(pydcH)(-)·H(2)O, is a monohydrate of acridinium cations and a mono-deprotonated pyridine-2,6-dicarb-oxy-lic acid. The structure contains a range of non-covalent inter-actions, such as O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, as well as π-π stacking [range of centroid-centroid distances = 3.4783 (5)-3.8059 (5) Å]. The N-H⋯O hydrogen bond between the donor acridinium cation and the carboxyl-ate acceptor is particularly strong. The average separation between the π-stacked acridinium planes is 3.42 (3) Å.

Related literature

For structures of acridinium salts, see: Aghabozorg et al. (2010 ▶); Attar Gharamaleki et al. (2010 ▶); Derikvand et al. (2009 ▶, 2010 ▶); Shaameri et al. (2001 ▶); Tabatabaee et al. (2009 ▶).

Experimental

Crystal data

C13H10N+·C7H4NO4 −·H2O

M = 364.35

Triclinic,

a = 7.4842 (3) Å

b = 8.6850 (3) Å

c = 13.0305 (4) Å

α = 100.266 (3)°

β = 93.851 (2)°

γ = 97.766 (2)°

V = 822.16 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 90 K

0.32 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.982

11632 measured reflections

4403 independent reflections

4034 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.105

S = 1.07

4403 reflections

308 parameters

All H-atom parameters refined

Δρmax = 0.48 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053791/hg2777sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053791/hg2777Isup2.hkl

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

C13H10N+·C7H4NO4−·H2O	Z = 2
Mr = 364.35	F(000) = 380
Triclinic, P1	Dx = 1.472 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4842 (3) Å	Cell parameters from 7626 reflections
b = 8.6850 (3) Å	θ = 2.6–32.9°
c = 13.0305 (4) Å	µ = 0.11 mm−1
α = 100.266 (3)°	T = 90 K
β = 93.851 (2)°	Block, yellow
γ = 97.766 (2)°	0.32 × 0.23 × 0.17 mm
V = 822.16 (5) Å3

Bruker SMART APEXII diffractometer	4403 independent reflections
Radiation source: fine-focus sealed tube	4034 reflections with I > 2σ(I)
graphite	Rint = 0.011
Detector resolution: 8.3 pixels mm-1	θmax = 29.1°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.966, Tmax = 0.982	l = −17→17
11632 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	All H-atom parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.1884P] where P = (Fo2 + 2Fc2)/3
4403 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.20 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	0.49045 (9)	0.63220 (8)	0.25575 (5)	0.02109 (15)
O2	0.19185 (9)	0.63670 (8)	0.23357 (5)	0.01783 (14)
O3	0.62172 (10)	0.08319 (8)	−0.08226 (5)	0.02271 (16)
O4	0.75469 (9)	0.23901 (8)	0.06409 (6)	0.02201 (15)
H4A	0.735 (2)	0.320 (2)	0.1097 (13)	0.043 (4)*
O5	0.81245 (10)	0.49602 (9)	0.22739 (6)	0.02321 (16)
H5A	0.721 (2)	0.544 (2)	0.2252 (13)	0.044 (4)*
H5B	0.907 (2)	0.560 (2)	0.2244 (13)	0.043 (4)*
N1	0.22761 (10)	0.86086 (8)	0.39668 (6)	0.01351 (15)
H1	0.215 (2)	0.771 (2)	0.3318 (14)	0.049 (5)*
N2	0.46280 (10)	0.38054 (8)	0.09346 (5)	0.01356 (15)
C1	0.29254 (11)	0.83725 (10)	0.49119 (6)	0.01346 (16)
C2	0.33756 (12)	0.68689 (11)	0.50193 (7)	0.01783 (18)
H2	0.3209 (19)	0.6010 (17)	0.4401 (11)	0.029 (3)*
C3	0.40456 (13)	0.66579 (12)	0.59791 (8)	0.02161 (19)
H3	0.432 (2)	0.5632 (18)	0.6068 (11)	0.034 (4)*
C4	0.43460 (13)	0.79225 (13)	0.68579 (8)	0.0226 (2)
H4	0.486 (2)	0.7719 (18)	0.7514 (12)	0.034 (4)*
C5	0.39282 (12)	0.93759 (12)	0.67742 (7)	0.01935 (18)
H5	0.418 (2)	1.0241 (17)	0.7378 (11)	0.031 (4)*
C6	0.31603 (11)	0.96397 (10)	0.57969 (6)	0.01448 (16)
C7	0.26325 (11)	1.10795 (10)	0.56689 (7)	0.01559 (17)
H7	0.2804 (19)	1.1941 (17)	0.6252 (11)	0.028 (3)*
C8	0.19056 (11)	1.12820 (10)	0.46937 (7)	0.01433 (17)
C9	0.13152 (12)	1.27198 (11)	0.45221 (8)	0.01948 (18)
H9	0.139 (2)	1.3590 (17)	0.5148 (11)	0.031 (3)*
C10	0.06669 (13)	1.28604 (12)	0.35436 (9)	0.0227 (2)
H10	0.026 (2)	1.3839 (18)	0.3435 (12)	0.037 (4)*
C11	0.05946 (13)	1.15875 (12)	0.26824 (8)	0.02219 (19)
H11	0.016 (2)	1.1712 (18)	0.1989 (12)	0.037 (4)*
C12	0.11412 (12)	1.01882 (11)	0.28081 (7)	0.01838 (18)
H12	0.1125 (19)	0.9325 (17)	0.2221 (11)	0.028 (3)*
C13	0.17760 (11)	1.00027 (10)	0.38252 (6)	0.01340 (16)
C14	0.31558 (11)	0.44843 (9)	0.11517 (6)	0.01310 (16)
C15	0.14892 (12)	0.39585 (11)	0.05742 (7)	0.01748 (17)
H15	0.0454 (18)	0.4460 (16)	0.0776 (10)	0.025 (3)*
C16	0.13303 (13)	0.26913 (12)	−0.02620 (7)	0.0224 (2)
H16	0.015 (2)	0.2304 (19)	−0.0658 (12)	0.039 (4)*
C17	0.28452 (13)	0.19891 (11)	−0.04975 (7)	0.02011 (19)
H17	0.280 (2)	0.1079 (17)	−0.1077 (11)	0.032 (4)*
C18	0.44547 (11)	0.25928 (10)	0.01274 (6)	0.01459 (16)
C19	0.33787 (12)	0.58364 (10)	0.20896 (6)	0.01463 (16)
C20	0.61355 (12)	0.18562 (10)	−0.00691 (7)	0.01689 (17)

	U11	U22	U33	U12	U13	U23
O1	0.0156 (3)	0.0221 (3)	0.0213 (3)	0.0021 (2)	−0.0019 (2)	−0.0053 (2)
O2	0.0154 (3)	0.0174 (3)	0.0187 (3)	0.0044 (2)	0.0012 (2)	−0.0031 (2)
O3	0.0247 (3)	0.0232 (3)	0.0206 (3)	0.0092 (3)	0.0066 (3)	−0.0007 (3)
O4	0.0159 (3)	0.0220 (3)	0.0267 (4)	0.0062 (2)	0.0003 (3)	−0.0013 (3)
O5	0.0150 (3)	0.0245 (4)	0.0307 (4)	0.0020 (3)	0.0008 (3)	0.0078 (3)
N1	0.0133 (3)	0.0131 (3)	0.0137 (3)	0.0024 (2)	0.0012 (2)	0.0011 (2)
N2	0.0139 (3)	0.0140 (3)	0.0130 (3)	0.0031 (2)	0.0014 (2)	0.0025 (2)
C1	0.0110 (3)	0.0146 (4)	0.0150 (4)	0.0015 (3)	0.0024 (3)	0.0034 (3)
C2	0.0157 (4)	0.0162 (4)	0.0233 (4)	0.0040 (3)	0.0048 (3)	0.0060 (3)
C3	0.0154 (4)	0.0251 (5)	0.0297 (5)	0.0067 (3)	0.0061 (3)	0.0153 (4)
C4	0.0149 (4)	0.0363 (5)	0.0199 (4)	0.0036 (4)	0.0020 (3)	0.0145 (4)
C5	0.0147 (4)	0.0290 (5)	0.0139 (4)	0.0005 (3)	0.0011 (3)	0.0052 (3)
C6	0.0117 (4)	0.0182 (4)	0.0127 (4)	−0.0002 (3)	0.0014 (3)	0.0025 (3)
C7	0.0145 (4)	0.0149 (4)	0.0153 (4)	−0.0005 (3)	0.0025 (3)	−0.0012 (3)
C8	0.0124 (4)	0.0128 (4)	0.0173 (4)	0.0006 (3)	0.0028 (3)	0.0020 (3)
C9	0.0169 (4)	0.0134 (4)	0.0286 (5)	0.0026 (3)	0.0049 (3)	0.0040 (3)
C10	0.0172 (4)	0.0194 (4)	0.0352 (5)	0.0051 (3)	0.0037 (4)	0.0126 (4)
C11	0.0169 (4)	0.0288 (5)	0.0237 (4)	0.0034 (3)	0.0001 (3)	0.0132 (4)
C12	0.0164 (4)	0.0230 (4)	0.0158 (4)	0.0024 (3)	−0.0001 (3)	0.0045 (3)
C13	0.0112 (3)	0.0141 (4)	0.0149 (4)	0.0015 (3)	0.0017 (3)	0.0029 (3)
C14	0.0145 (4)	0.0134 (4)	0.0114 (3)	0.0028 (3)	0.0012 (3)	0.0020 (3)
C15	0.0147 (4)	0.0221 (4)	0.0145 (4)	0.0056 (3)	−0.0003 (3)	−0.0011 (3)
C16	0.0162 (4)	0.0297 (5)	0.0172 (4)	0.0049 (3)	−0.0026 (3)	−0.0062 (3)
C17	0.0188 (4)	0.0231 (4)	0.0156 (4)	0.0041 (3)	0.0012 (3)	−0.0042 (3)
C18	0.0156 (4)	0.0152 (4)	0.0135 (4)	0.0041 (3)	0.0031 (3)	0.0022 (3)
C19	0.0159 (4)	0.0135 (4)	0.0139 (4)	0.0023 (3)	0.0011 (3)	0.0009 (3)
C20	0.0161 (4)	0.0170 (4)	0.0185 (4)	0.0040 (3)	0.0041 (3)	0.0038 (3)

O1—C19	1.2403 (11)	C6—C7	1.3952 (12)
O2—C19	1.2806 (10)	C7—C8	1.3980 (12)
O3—C20	1.2126 (11)	C7—H7	0.955 (14)
O4—C20	1.3305 (11)	C8—C13	1.4256 (11)
O4—H4A	0.869 (17)	C8—C9	1.4282 (12)
O5—H5A	0.849 (18)	C9—C10	1.3655 (14)
O5—H5B	0.845 (18)	C9—H9	1.002 (14)
N1—C1	1.3533 (11)	C10—C11	1.4204 (15)
N1—C13	1.3538 (11)	C10—H10	0.972 (16)
N1—H1	1.031 (17)	C11—C12	1.3665 (13)
N2—C18	1.3350 (11)	C11—H11	0.970 (16)
N2—C14	1.3415 (11)	C12—C13	1.4215 (12)
C1—C2	1.4199 (12)	C12—H12	0.969 (14)
C1—C6	1.4283 (11)	C14—C15	1.3885 (12)
C2—C3	1.3680 (13)	C14—C19	1.5194 (11)
C2—H2	0.984 (14)	C15—C16	1.3901 (12)
C3—C4	1.4208 (15)	C15—H15	0.968 (14)
C3—H3	0.966 (15)	C16—C17	1.3850 (13)
C4—C5	1.3617 (14)	C16—H16	0.977 (16)
C4—H4	0.969 (15)	C17—C18	1.3908 (12)
C5—C6	1.4303 (12)	C17—H17	0.987 (15)
C5—H5	0.975 (14)	C18—C20	1.5032 (12)
C20—O4—H4A	112.1 (11)	C9—C10—C11	120.43 (9)
H5A—O5—H5B	109.3 (16)	C9—C10—H10	119.8 (9)
C1—N1—C13	122.44 (7)	C11—C10—H10	119.7 (9)
C1—N1—H1	120.2 (10)	C12—C11—C10	121.37 (9)
C13—N1—H1	117.3 (10)	C12—C11—H11	119.0 (9)
C18—N2—C14	117.75 (7)	C10—C11—H11	119.6 (9)
N1—C1—C2	119.91 (8)	C11—C12—C13	119.08 (9)
N1—C1—C6	119.81 (8)	C11—C12—H12	121.8 (8)
C2—C1—C6	120.28 (8)	C13—C12—H12	119.1 (8)
C3—C2—C1	119.03 (9)	N1—C13—C12	119.76 (8)
C3—C2—H2	121.8 (8)	N1—C13—C8	119.91 (7)
C1—C2—H2	119.2 (8)	C12—C13—C8	120.32 (8)
C2—C3—C4	121.31 (9)	N2—C14—C15	122.24 (8)
C2—C3—H3	119.9 (9)	N2—C14—C19	116.69 (7)
C4—C3—H3	118.8 (9)	C15—C14—C19	121.05 (7)
C5—C4—C3	120.73 (8)	C14—C15—C16	119.29 (8)
C5—C4—H4	121.3 (9)	C14—C15—H15	119.3 (8)
C3—C4—H4	118.0 (9)	C16—C15—H15	121.4 (8)
C4—C5—C6	120.05 (9)	C17—C16—C15	118.93 (8)
C4—C5—H5	119.8 (9)	C17—C16—H16	121.7 (9)
C6—C5—H5	120.1 (9)	C15—C16—H16	119.3 (9)
C7—C6—C1	118.53 (8)	C16—C17—C18	117.69 (8)
C7—C6—C5	122.96 (8)	C16—C17—H17	122.0 (9)
C1—C6—C5	118.52 (8)	C18—C17—H17	120.3 (9)
C6—C7—C8	120.73 (8)	N2—C18—C17	124.10 (8)
C6—C7—H7	119.2 (9)	N2—C18—C20	115.58 (7)
C8—C7—H7	120.0 (9)	C17—C18—C20	120.31 (8)
C7—C8—C13	118.48 (8)	O1—C19—O2	125.44 (8)
C7—C8—C9	123.10 (8)	O1—C19—C14	119.23 (8)
C13—C8—C9	118.42 (8)	O2—C19—C14	115.33 (7)
C10—C9—C8	120.32 (9)	O3—C20—O4	121.35 (8)
C10—C9—H9	122.8 (8)	O3—C20—C18	122.73 (8)
C8—C9—H9	116.9 (8)	O4—C20—C18	115.92 (7)
C13—N1—C1—C2	178.05 (7)	C11—C12—C13—N1	178.23 (8)
C13—N1—C1—C6	−2.15 (12)	C11—C12—C13—C8	−2.42 (13)
N1—C1—C2—C3	179.41 (8)	C7—C8—C13—N1	2.91 (12)
C6—C1—C2—C3	−0.39 (13)	C9—C8—C13—N1	−178.14 (7)
C1—C2—C3—C4	−1.84 (13)	C7—C8—C13—C12	−176.43 (8)
C2—C3—C4—C5	1.74 (14)	C9—C8—C13—C12	2.51 (12)
C3—C4—C5—C6	0.66 (14)	C18—N2—C14—C15	0.51 (12)
N1—C1—C6—C7	2.80 (12)	C18—N2—C14—C19	178.61 (7)
C2—C1—C6—C7	−177.40 (8)	N2—C14—C15—C16	−0.32 (14)
N1—C1—C6—C5	−177.12 (7)	C19—C14—C15—C16	−178.35 (8)
C2—C1—C6—C5	2.68 (12)	C14—C15—C16—C17	−0.15 (15)
C4—C5—C6—C7	177.28 (8)	C15—C16—C17—C18	0.39 (15)
C4—C5—C6—C1	−2.80 (13)	C14—N2—C18—C17	−0.24 (13)
C1—C6—C7—C8	−0.59 (12)	C14—N2—C18—C20	−178.89 (7)
C5—C6—C7—C8	179.32 (8)	C16—C17—C18—N2	−0.21 (15)
C6—C7—C8—C13	−2.20 (12)	C16—C17—C18—C20	178.38 (9)
C6—C7—C8—C9	178.91 (8)	N2—C14—C19—O1	5.15 (12)
C7—C8—C9—C10	178.03 (8)	C15—C14—C19—O1	−176.72 (8)
C13—C8—C9—C10	−0.87 (13)	N2—C14—C19—O2	−173.96 (7)
C8—C9—C10—C11	−0.86 (14)	C15—C14—C19—O2	4.17 (12)
C9—C10—C11—C12	0.97 (14)	N2—C18—C20—O3	−173.96 (8)
C10—C11—C12—C13	0.68 (14)	C17—C18—C20—O3	7.33 (14)
C1—N1—C13—C12	178.61 (7)	N2—C18—C20—O4	6.37 (11)
C1—N1—C13—C8	−0.74 (12)	C17—C18—C20—O4	−172.34 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O5	0.869 (17)	1.958 (17)	2.7604 (10)	152.9 (16)
O4—H4A···N2	0.869 (17)	2.182 (17)	2.6646 (10)	114.6 (14)
O5—H5A···O1	0.849 (18)	2.016 (18)	2.8421 (10)	164.0 (16)
O5—H5B···O2i	0.845 (18)	2.134 (18)	2.9255 (10)	155.8 (16)
N1—H1···O2	1.031 (17)	1.555 (18)	2.5859 (9)	178.6 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O5	0.869 (17)	1.958 (17)	2.7604 (10)	152.9 (16)
O4—H4A⋯N2	0.869 (17)	2.182 (17)	2.6646 (10)	114.6 (14)
O5—H5A⋯O1	0.849 (18)	2.016 (18)	2.8421 (10)	164.0 (16)
O5—H5B⋯O2i	0.845 (18)	2.134 (18)	2.9255 (10)	155.8 (16)
N1—H1⋯O2	1.031 (17)	1.555 (18)	2.5859 (9)	178.6 (16)

Symmetry code: (i) .