Acridinium 3,5-dicarboxy­benzoate monohydrate

Derikvand, Z.; Aghabozorg, H.; Attar Gharamaleki, J.

doi:10.1107/S1600536809015529

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1173

doi:10.1107/S1600536809015529

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Acridinium 3,5-dicarboxybenzoate monohydrate

Zohreh Derikvand,^a ^* Hossein Aghabozorg ^b and Jafar Attar Gharamaleki ^c

^aFaculty of Science, Department of Chemistry, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, ^bFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^cFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran
^*Correspondence e-mail: zderik@yahoo.com

(Received 13 April 2009; accepted 25 April 2009; online 30 April 2009)

The title compound, C₁₃H₁₀N⁺·C₉H₅O₆⁻·H₂O, exhibits a wide range of non-covalent interactions, 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 supramolecular 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_r = 407.37
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.130
S = 1.01
4275 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) -x+2, -y, -z; (ii) -x, -y+1, -z; (iii) x-1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Acridine is structurally related to anthracene wherein one of the central CH groups is replaced by nitrogen. It is a raw material used for the production of dyes and some valuable drugs. Our research group has reported the first proton transfer complex with acridine (Tabatabaee et al., 2009). We have also reported many proton transfer compounds with various donor and acceptor fragments; further details and related literature has been presented in a review article (Aghabozorg et al., 2008). In this article, we report the crystal structure of a proton transfer system containing acridine and benzene tricarboxylic acid.

The title structure contains a cation, an anion and a water molecule in an asymmetric unit (Fig. 1). The crystal structure shows that one of the protons of carboxylic groups has been transferred to nitrogen atom of the acridine molecule. Noncovalent interactions cause the structure to form a self-assembled system. A hydrogen bonded motif involving anion and cation fragments and water molecules linked to each other into one-dimensional chains is presented in Fig. 2; details of O–H···O and N–H···O hydrogen bonds are shown in Table 1. In addition, the interactions consisting of ion-pairing, π–π stacking [with centroid-centroid distances = 3.562 (8) and 3.872 (8) Å] between two cations are also present (Fig. 3).

The crystal structures of several acridine derivatives have been reported recently (Zadykowicz, Trzybiński et al., 2009; Zadykowicz, Krzymiński et al., 2009; Trzybiński et al., 2009.

Related literature top

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 top

The reaction between solution benzene tricarboxylic acid (10 mg, 1 mmol) in 10 ml water and acridine (89 mg, 2 mmol) in 10 ml me thanol in 1:2 molar ratios gave brown prism crystals after slow evaporation of the solvent at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. One-dimensional chain that formed by hydrogen bonds between cationic and anionic fragments and water molecules.
	Fig. 3. π–π Stacking interactions between cationic fragments in the title compound.

Acridinium 3,5-dicarboxybenzoate monohydrate top

Crystal data top

C₁₃H₁₀N⁺·C₉H₅O₆⁻·H₂O	Z = 2
M_r = 407.37	F(000) = 424
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.046	Hydrogen site location: mixed
wR(F²) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.08P)² + 0.36P] where P = (F_o² + 2F_c²)/3
4275 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₀N⁺·C₉H₅O₆⁻·H₂O	γ = 103.310 (1)°
M_r = 407.37	V = 901.62 (10) Å³
Triclinic, P1	Z = 2
a = 6.8554 (4) Å	Mo Kα radiation
b = 9.6930 (6) Å	µ = 0.11 mm⁻¹
c = 14.8916 (10) Å	T = 120 K
α = 103.687 (1)°	0.25 × 0.20 × 0.15 mm
β = 101.424 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4275 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	3659 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.980	R_int = 0.018
9138 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.01	Δρ_max = 0.36 e Å⁻³
4275 reflections	Δρ_min = −0.30 e Å⁻³
271 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	0.53402 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z; (ii) −x, −y+1, −z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N⁺·C₉H₅O₆⁻·H₂O
M_r	407.37
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	6.8554 (4), 9.6930 (6), 14.8916 (10)
α, β, γ (°)	103.687 (1), 101.424 (1), 103.310 (1)
V (Å³)	901.62 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.971, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	9138, 4275, 3659
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.130, 1.01
No. of reflections	4275
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z; (ii) −x, −y+1, −z; (iii) x−1, y, z.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1998). 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
Trzybiński, D., Skupień, M., Krzymiński, K., Sikorski, A. & Błażejowski, J. (2009). Acta Cryst. E65, o770–o771. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zadykowicz, B., Krzymiński, K., Trzybiński, D., Sikorski, A. & Błażejowski, J. (2009). Acta Cryst. E65, o768–o769. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zadykowicz, B., Trzybiński, D., Sikorski, A. & Błażejowski, J. (2009). Acta Cryst. E65, o566–o567. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 5| May 2009| Page o1173

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