Acridinium 6-carb­oxy­pyridine-2-carboxyl­ate monohydrate

Derikvand, Z.; Olmstead, M.M.; Attar Gharamaleki, J.

doi:10.1107/S1600536810053791

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o416

doi:10.1107/S1600536810053791

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Acridinium 6-carboxypyridine-2-carboxylate monohydrate

Zohreh Derikvand,^a ^* Marilyn M. Olmstead ^b and Jafar Attar Gharamaleki ^c

^aDepartment of Chemistry, Faculty of Sciences, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, ^bDepartment of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA, and ^cYoung Researchers Club, Islamic Azad University, North Tehran Branch, Tehran, Iran
^*Correspondence e-mail: zderik@yahoo.com

(Received 18 December 2010; accepted 22 December 2010; online 15 January 2011)

The title compound, C₁₃H₁₀N⁺·C₇H₄NO₄⁻·H₂O or (acrH)⁺(pydcH)⁻·H₂O, is a monohydrate of acridinium cations and a mono-deprotonated pyridine-2,6-dicarboxylic acid. The structure contains a range of non-covalent interactions, 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 carboxylate 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_r = 364.35
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.105
S = 1.07
4403 reflections
308 parameters
All H-atom parameters refined
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) x+1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

We have reported a number of crystal structures of protonated acridine and pyridine dicarboxylates (Derikvand et al., 2009, 2010; Aghabozorg et al., 2010; Attar Gharamaleki et al., 2010; Tabatabaee et al., 2009). Many other examples of acridinium salts are known, and they have π–π stacking of the acridinium ions and various types of hydrogen bonding in common. The molecular structure of the title compound, the 1:1 salt of acridinium and pydridine-2,6-dicarboylate is illustrated in Fig. 1. The crystal structure shows one of the protons of the two carboxylic groups has been transferred to the nitrogen atom of the acridine molecule.

As expected, bond lengths of the –CO₂ groups reflect the presence or lack of an acidic H atom. At distances of 1.2403 (11) Å and 1.2806 (1)) Å, respectively, the O1—C19 and O2—C19 bond lengths are much closer to equality than O3—C20 and O4—C20, at 1.226 (11) Å and 1.3305 (11) Å. However, we can also point out that the O2—C19 bond is slightly longer than the O1—C19 bond, possibly due to there being two classical hydrogen bonds involving O2 and only one involving O1 (see Table 1). In fact, one of the hydrogen bonds for O2 can be classified as a very strong hydrogen bond, with an N···O distance of 2.5859 (9) Å. In a similar structure involving the acridinium salt of isophthalate (Shaameri et al., 2001), the analogous arrangement of cation and anion gives rise to a similar short hydrogen bond with N···O distance of 2.553 (2) Å. A depiction of the hydrogen bonded motif involving anion and cation fragments and water molecules is presented in Fig. 2. The hydrogen bonds between the water molecule and O2 serve to link the anions into a chain along the a axis direction. Symmetry code: i = x - 1, y, z.

Additional noncovalent interactions cause the structure to form a self assembled system. In the structure π–π stacking interactions between the acridinium ions average 3.42[3]Å (average deviation in square brackets). Sideways strong hydrogen bonds between O2 and the the proton of acridine gather the π-stack and the anionic chain together as shown in Fig. 3.

Related literature top

For structure of acridinium salts, see: Aghabozorg et al. (2010); Attar Gharamaleki Derikvand & Stoeckli-Evans (2010); Derikvand et al. (2009, 2010); Shaameri et al. (2001); Tabatabaee et al. (2009).

Experimental top

A solution of pyridine-2,6-dicarboxylic acid (167 mg, 1 mmol) in water (10 ml) was added to a solution of acridine(179 mg, 1 mmol) in methanol (5 ml) and stirring for 30 minutes, a clear solution was obtained (Scheme 1). Yellow-gold block crystals suitable for X-ray crystallography were produced by slow evaporation of the solvent at room temperature after a week.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (acrH)⁺(pydcH)^-. H₂O. Displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. Hydrogen bonding interactions. Symmetry code: i = x - 1, y, z.
	Fig. 3. π–π Stacking interactions between cationic fragments and their link to anionic chains as viewed along [0 1 1].

Acridinium 6-carboxypyridine-2-carboxylate monohydrate top

Crystal data top

C₁₃H₁₀N⁺·C₇H₄NO₄⁻·H₂O	Z = 2
M_r = 364.35	F(000) = 380
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0621P)² + 0.1884P] where P = (F_o² + 2F_c²)/3
4403 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₁₀N⁺·C₇H₄NO₄⁻·H₂O	γ = 97.766 (2)°
M_r = 364.35	V = 822.16 (5) Å³
Triclinic, P1	Z = 2
a = 7.4842 (3) Å	Mo Kα radiation
b = 8.6850 (3) Å	µ = 0.11 mm⁻¹
c = 13.0305 (4) Å	T = 90 K
α = 100.266 (3)°	0.32 × 0.23 × 0.17 mm
β = 93.851 (2)°

Data collection top

Bruker SMART APEXII diffractometer	4403 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4034 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.982	R_int = 0.011
11632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.105	All H-atom parameters refined
S = 1.07	Δρ_max = 0.48 e Å⁻³
4403 reflections	Δρ_min = −0.20 e Å⁻³
308 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N⁺·C₇H₄NO₄⁻·H₂O
M_r	364.35
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	7.4842 (3), 8.6850 (3), 13.0305 (4)
α, β, γ (°)	100.266 (3), 93.851 (2), 97.766 (2)
V (Å³)	822.16 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.23 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	11632, 4403, 4034
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.105, 1.07
No. of reflections	4403
No. of parameters	308
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

References

Aghabozorg, H., Attar Gharamaleki, J., Parvizi, M. & Derikvand, Z. (2010). Acta Cryst. E66, m83–m84. Web of Science CSD CrossRef IUCr Journals Google Scholar
Attar Gharamaleki, J., Derikvand, Z. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, o2231. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Derikvand, Z., Aghabozorg, H. & Attar Gharamaleki, J. (2009). Acta Cryst. E65, o1173. Web of Science CSD CrossRef IUCr Journals Google Scholar
Derikvand, Z., Attar Gharamaleki, J. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, m1316–m1317. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shaameri, Z., Shan, N. & Jones, W. (2001). Acta Cryst. E57, o945–o946. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tabatabaee, M., Aghabozorg, H., Attar Gharamaleki, J. & Sharif, M. A. (2009). Acta Cryst. E65, m473–m474. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o416

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