1,10-Phenanthrolinium 2′-carboxy­biphenyl-2-carboxyl­ate

Wang, C.

doi:10.1107/S1600536809036551

organic compounds

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Volume 65| Part 10| October 2009| Page o2478

doi:10.1107/S1600536809036551

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1,10-Phenanthrolinium 2′-carboxybiphenyl-2-carboxylate

Chongchen Wang ^a ^*

^aSchool of Environmental and Energy Engineering, Beijing University of Civil Engineering and Architecture, 100044 Beijing, People's Republic of China
^*Correspondence e-mail: chongchenwang@126.com

(Received 3 August 2009; accepted 9 September 2009; online 16 September 2009)

The title complex, C₁₂H₉N₂⁺·C₁₄H₉O₄⁻ or (Hphen)⁺(Hbptc)⁻ [H₂btc = 2,2′-biphenyldicarboxylic acid and phen = 1,10-phenanthroline], has been synthesized under hydrothermal conditions. The compound is composed of discrete cations (Hphen)⁺ and anions (Hbptc)⁻, which are linked by electrovalent bonding; the molecular and crystal structures are further strengthened by intramolecular O—H⋯O and intermolecular N—H⋯O hydrogen bonds.

Related literature

For the applications of the metal-organic coordination compounds constructed from biphenydicarboxylic acid, see: Gao & Cheng (2004 ).

Experimental

Crystal data

C₁₂H₉N₂⁺·C₁₄H₉O₄⁻
M_r = 422.42
Monoclinic, P 2₁ /c
a = 12.1661 (13) Å
b = 7.389 (1) Å
c = 22.160 (2) Å
β = 91.061 (1)°
V = 1991.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.48 × 0.45 × 0.37 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.955, T_max = 0.965
9415 measured reflections
3479 independent reflections
1771 reflections with I > 2σ(I)
R_int = 0.102

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.243
S = 1.01
3479 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.82	2.643 (4)	161
O3—H3⋯O1	0.82	1.75	2.559 (4)	172
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809036551/ez2179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036551/ez2179Isup2.hkl

checkCIF report

Comment top

1,10-phenanthroline and 2,2'-biphenyldicarboxylic acid are both versatile ligands, which have been used in the self-assembly of various coordination compounds. The crystals of the title compound were obtained unintentionally as the harvested product of the hydrothermal reaction between Ce₂O₃ and 1,10-phenanthroline in the presence of 2,2'-biphenyldicarboxylic acid.

In the crystal of the title compound, 1,10-phenanthroline is protonated into the cation 1,10-phenanthrolinium [(Hphen)⁺], as indicated by the presence of a peak of electron density on the difference Fourier map at an appropriate distance from N1. The 2,2'-biphenydicarboxylic acid has been deprotonated into the anion biphenyldicarboxylate [(Hbptc)^-], with the similar C—O distances on the deprotonated carboxylate indicating delocalisation (O1—C1=1.274 (5); O2—C1=1.221 (5)Å), whereas the C—O distances in the carboxylic acid group (O3—C14=1.315 (5); O4—C14=1.197 (5) Å) correspond to single and double bonds, respectively. The discrete cations (Hphen)⁺ and anions (Hbptc)^- are linked by an electrovalent bond, and further strengthened by intermolecular N1—H1···O1ⁱ(Symmetry operator, i: -x + 1, y + 1/2, -z + 1/2) and intramolecular O3—H3···O1 hydrogen bonds.

The phenyl rings of the 2,2'-biphenyldicarboxylate are not coplanar, but twisted almost perpendicular to each other with a dihedral angle between the planes through the two rings of 86.06(0.13) °.

Related literature top

For the applications of the metal-organic coordination compounds constructed from biphenydicarboxylic acid, see: Gao & Cheng (2004).

Experimental top

The mixture of 2,2'-biphenydicarboxylic acid (0.04884 g), 1,10-phenanthroline (0.0360 g), Ce₂O₃ (0.0702 g) and deionized water (15 ml) was heated in a 23 ml teflon-lined reaction vessel at 433 K for 120 h to carry out the hydrothermal reaction. After slow cooling to room temperature the mixture was filtered, and the clear solution obtained was allowed to evaporate slowly at room temperature. After about 10 days, yellow block-like crystals of the title compound were harvested.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. ORTEP drawing of the title compound showing the atom labelling scheme. Ellipsoids are drawn at the 30% level.
	Fig. 2. The crystal packing of the title complex. Hydrogen bonds are indicated by dashed lines.

1,10-Phenanthrolinium 2'-carboxybiphenyl-2-carboxylate top

Crystal data top

C₁₂H₉N₂⁺·C₁₄H₉O₄⁻	F(000) = 880
M_r = 422.42	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1661 (13) Å	Cell parameters from 1541 reflections
b = 7.389 (1) Å	θ = 2.5–21.4°
c = 22.160 (2) Å	µ = 0.10 mm⁻¹
β = 91.061 (1)°	T = 298 K
V = 1991.8 (4) Å³	Block, brown
Z = 4	0.48 × 0.45 × 0.37 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3479 independent reflections
Radiation source: fine-focus sealed tube	1771 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.102
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→14
T_min = 0.955, T_max = 0.965	k = −8→7
9415 measured reflections	l = −22→26

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.243	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0849P)² + 0.7223P] where P = (F_o² + 2F_c²)/3
3479 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·C₁₄H₉O₄⁻	V = 1991.8 (4) Å³
M_r = 422.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1661 (13) Å	µ = 0.10 mm⁻¹
b = 7.389 (1) Å	T = 298 K
c = 22.160 (2) Å	0.48 × 0.45 × 0.37 mm
β = 91.061 (1)°

Data collection top

Bruker SMART CCD area detector diffractometer	3479 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1771 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.965	R_int = 0.102
9415 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.243	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
3479 reflections	Δρ_min = −0.29 e Å⁻³
289 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
N1	0.4893 (3)	0.7686 (4)	0.46216 (17)	0.0382 (9)
H1	0.5462	0.8170	0.4464	0.046*
N2	0.6719 (3)	0.8548 (5)	0.52863 (18)	0.0486 (11)
O1	0.3597 (2)	0.4014 (4)	0.10974 (14)	0.0472 (8)
O2	0.4735 (2)	0.3641 (5)	0.18797 (16)	0.0674 (11)
O3	0.1925 (2)	0.5887 (4)	0.07606 (14)	0.0491 (9)
H3	0.2419	0.5210	0.0878	0.074*
O4	0.0140 (3)	0.5855 (4)	0.06817 (18)	0.0685 (11)
C1	0.3850 (3)	0.4087 (6)	0.1657 (2)	0.0411 (11)
C2	0.3001 (3)	0.4868 (5)	0.20651 (19)	0.0349 (10)
C3	0.3300 (3)	0.6209 (6)	0.2472 (2)	0.0447 (12)
H3A	0.4031	0.6573	0.2498	0.054*
C4	0.2558 (4)	0.7001 (6)	0.2831 (2)	0.0493 (12)
H4	0.2780	0.7916	0.3095	0.059*
C5	0.1464 (4)	0.6457 (6)	0.2811 (2)	0.0505 (13)
H5	0.0950	0.7002	0.3057	0.061*
C6	0.1159 (3)	0.5112 (6)	0.2422 (2)	0.0438 (11)
H6	0.0433	0.4714	0.2417	0.053*
C7	0.1900 (3)	0.4322 (5)	0.20367 (19)	0.0344 (10)
C8	0.1484 (3)	0.2851 (5)	0.1628 (2)	0.0347 (10)
C9	0.1496 (3)	0.1076 (6)	0.1828 (2)	0.0442 (12)
H9	0.1820	0.0787	0.2199	0.053*
C10	0.1030 (4)	−0.0250 (6)	0.1479 (2)	0.0505 (13)
H10	0.1074	−0.1447	0.1607	0.061*
C11	0.0497 (4)	0.0149 (6)	0.0943 (2)	0.0548 (13)
H11	0.0156	−0.0762	0.0718	0.066*
C12	0.0474 (3)	0.1894 (6)	0.0745 (2)	0.0466 (12)
H12	0.0116	0.2177	0.0383	0.056*
C13	0.0983 (3)	0.3256 (5)	0.1082 (2)	0.0358 (10)
C14	0.0970 (3)	0.5087 (6)	0.0828 (2)	0.0413 (11)
C15	0.4040 (3)	0.7289 (6)	0.4267 (2)	0.0461 (12)
H15	0.4063	0.7534	0.3856	0.055*
C16	0.3115 (3)	0.6510 (6)	0.4508 (3)	0.0526 (14)
H16	0.2507	0.6248	0.4263	0.063*
C17	0.3104 (4)	0.6130 (6)	0.5107 (3)	0.0517 (13)
H17	0.2485	0.5592	0.5270	0.062*
C18	0.4003 (3)	0.6533 (5)	0.5482 (2)	0.0417 (11)
C19	0.4904 (3)	0.7367 (5)	0.5213 (2)	0.0371 (11)
C20	0.5865 (3)	0.7782 (6)	0.5575 (2)	0.0421 (11)
C21	0.5874 (4)	0.7370 (6)	0.6186 (2)	0.0503 (13)
C22	0.6842 (5)	0.7747 (7)	0.6519 (2)	0.0632 (15)
H22	0.6893	0.7497	0.6930	0.076*
C23	0.7701 (4)	0.8488 (7)	0.6223 (3)	0.0667 (16)
H23	0.8354	0.8736	0.6431	0.080*
C24	0.7609 (4)	0.8868 (7)	0.5623 (2)	0.0568 (14)
H24	0.8211	0.9386	0.5436	0.068*
C25	0.4055 (4)	0.6151 (7)	0.6106 (3)	0.0570 (14)
H25	0.3450	0.5622	0.6287	0.068*
C26	0.4940 (4)	0.6525 (7)	0.6443 (3)	0.0590 (14)
H26	0.4951	0.6231	0.6851	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0245 (18)	0.044 (2)	0.046 (3)	−0.0031 (15)	0.0015 (16)	0.0019 (18)
N2	0.033 (2)	0.061 (3)	0.052 (3)	−0.0009 (18)	−0.0029 (18)	0.0035 (19)
O1	0.0283 (16)	0.074 (2)	0.039 (2)	0.0077 (14)	0.0005 (14)	−0.0034 (17)
O2	0.0330 (18)	0.106 (3)	0.063 (3)	0.0231 (18)	−0.0067 (16)	0.001 (2)
O3	0.0361 (17)	0.0474 (18)	0.064 (2)	0.0008 (14)	−0.0022 (15)	0.0129 (16)
O4	0.0416 (19)	0.052 (2)	0.111 (3)	0.0062 (16)	−0.0257 (19)	0.004 (2)
C1	0.026 (2)	0.047 (3)	0.050 (3)	0.0011 (19)	0.005 (2)	0.001 (2)
C2	0.029 (2)	0.037 (2)	0.038 (3)	0.0025 (18)	−0.0028 (18)	0.001 (2)
C3	0.031 (2)	0.053 (3)	0.050 (3)	−0.005 (2)	−0.009 (2)	0.003 (2)
C4	0.056 (3)	0.047 (3)	0.045 (3)	0.007 (2)	−0.009 (2)	−0.008 (2)
C5	0.041 (3)	0.059 (3)	0.051 (3)	0.007 (2)	0.001 (2)	−0.012 (2)
C6	0.032 (2)	0.052 (3)	0.047 (3)	0.004 (2)	0.003 (2)	−0.002 (2)
C7	0.027 (2)	0.038 (2)	0.038 (3)	0.0013 (18)	−0.0018 (18)	0.0033 (19)
C8	0.024 (2)	0.034 (2)	0.046 (3)	0.0014 (17)	0.0036 (19)	−0.004 (2)
C9	0.038 (2)	0.042 (3)	0.053 (3)	0.001 (2)	0.003 (2)	0.001 (2)
C10	0.055 (3)	0.034 (3)	0.063 (4)	0.000 (2)	0.012 (3)	0.001 (2)
C11	0.055 (3)	0.044 (3)	0.065 (4)	−0.010 (2)	0.002 (3)	−0.014 (3)
C12	0.038 (3)	0.043 (3)	0.059 (4)	−0.004 (2)	−0.002 (2)	−0.011 (2)
C13	0.026 (2)	0.037 (2)	0.044 (3)	0.0005 (18)	−0.0017 (19)	−0.001 (2)
C14	0.033 (3)	0.042 (3)	0.049 (3)	0.002 (2)	−0.009 (2)	−0.007 (2)
C15	0.033 (2)	0.051 (3)	0.055 (3)	0.001 (2)	−0.005 (2)	0.000 (2)
C16	0.026 (2)	0.059 (3)	0.073 (4)	−0.007 (2)	0.000 (2)	−0.011 (3)
C17	0.038 (3)	0.046 (3)	0.072 (4)	−0.005 (2)	0.016 (3)	−0.008 (3)
C18	0.038 (3)	0.035 (2)	0.053 (3)	0.0052 (19)	0.013 (2)	−0.001 (2)
C19	0.032 (2)	0.035 (2)	0.044 (3)	0.0055 (18)	0.005 (2)	0.001 (2)
C20	0.039 (3)	0.038 (2)	0.049 (3)	0.011 (2)	0.004 (2)	−0.002 (2)
C21	0.061 (3)	0.045 (3)	0.045 (3)	0.010 (2)	0.000 (2)	0.000 (2)
C22	0.073 (4)	0.072 (4)	0.045 (4)	0.010 (3)	−0.009 (3)	0.002 (3)
C23	0.055 (3)	0.083 (4)	0.062 (4)	0.000 (3)	−0.012 (3)	−0.001 (3)
C24	0.038 (3)	0.073 (4)	0.059 (4)	−0.002 (2)	−0.009 (2)	0.002 (3)
C25	0.055 (3)	0.056 (3)	0.061 (4)	0.007 (3)	0.021 (3)	0.009 (3)
C26	0.068 (4)	0.060 (3)	0.050 (4)	0.015 (3)	0.016 (3)	0.012 (3)

Geometric parameters (Å, º) top

N1—C15	1.324 (5)	C10—H10	0.9300
N1—C19	1.332 (5)	C11—C12	1.363 (6)
N1—H1	0.8600	C11—H11	0.9300
N2—C24	1.324 (6)	C12—C13	1.392 (6)
N2—C20	1.354 (5)	C12—H12	0.9300
O1—C1	1.274 (5)	C13—C14	1.465 (6)
O2—C1	1.221 (5)	C15—C16	1.380 (6)
O3—C14	1.315 (5)	C15—H15	0.9300
O3—H3	0.8200	C16—C17	1.356 (7)
O4—C14	1.197 (5)	C16—H16	0.9300
C1—C2	1.501 (6)	C17—C18	1.395 (6)
C2—C3	1.384 (6)	C17—H17	0.9300
C2—C7	1.399 (5)	C18—C19	1.401 (6)
C3—C4	1.348 (6)	C18—C25	1.412 (7)
C3—H3A	0.9300	C19—C20	1.437 (6)
C4—C5	1.391 (6)	C20—C21	1.390 (7)
C4—H4	0.9300	C21—C22	1.406 (7)
C5—C6	1.361 (6)	C21—C26	1.424 (7)
C5—H5	0.9300	C22—C23	1.359 (7)
C6—C7	1.383 (6)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.363 (7)
C7—C8	1.497 (6)	C23—H23	0.9300
C8—C13	1.379 (6)	C24—H24	0.9300
C8—C9	1.384 (6)	C25—C26	1.328 (7)
C9—C10	1.364 (6)	C25—H25	0.9300
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.376 (7)

C15—N1—C19	122.6 (4)	C8—C13—C14	122.6 (4)
C15—N1—H1	118.7	C12—C13—C14	117.4 (4)
C19—N1—H1	118.7	O4—C14—O3	119.9 (4)
C24—N2—C20	115.8 (4)	O4—C14—C13	123.0 (4)
C14—O3—H3	109.5	O3—C14—C13	117.1 (4)
O2—C1—O1	125.2 (4)	N1—C15—C16	119.9 (5)
O2—C1—C2	118.2 (4)	N1—C15—H15	120.1
O1—C1—C2	116.5 (4)	C16—C15—H15	120.1
C3—C2—C7	118.4 (4)	C17—C16—C15	119.3 (4)
C3—C2—C1	119.5 (4)	C17—C16—H16	120.4
C7—C2—C1	122.1 (4)	C15—C16—H16	120.4
C4—C3—C2	121.7 (4)	C16—C17—C18	121.1 (4)
C4—C3—H3A	119.2	C16—C17—H17	119.4
C2—C3—H3A	119.2	C18—C17—H17	119.4
C3—C4—C5	120.4 (4)	C17—C18—C19	116.9 (5)
C3—C4—H4	119.8	C17—C18—C25	124.2 (5)
C5—C4—H4	119.8	C19—C18—C25	118.9 (4)
C6—C5—C4	118.8 (4)	N1—C19—C18	120.2 (4)
C6—C5—H5	120.6	N1—C19—C20	120.3 (4)
C4—C5—H5	120.6	C18—C19—C20	119.4 (4)
C5—C6—C7	121.7 (4)	N2—C20—C21	124.1 (4)
C5—C6—H6	119.2	N2—C20—C19	116.7 (4)
C7—C6—H6	119.2	C21—C20—C19	119.2 (4)
C6—C7—C2	119.0 (4)	C20—C21—C22	117.4 (5)
C6—C7—C8	117.6 (3)	C20—C21—C26	119.6 (5)
C2—C7—C8	123.4 (4)	C22—C21—C26	123.0 (5)
C13—C8—C9	119.2 (4)	C23—C22—C21	118.1 (5)
C13—C8—C7	120.8 (4)	C23—C22—H22	121.0
C9—C8—C7	119.6 (4)	C21—C22—H22	121.0
C10—C9—C8	119.9 (5)	C22—C23—C24	120.3 (5)
C10—C9—H9	120.1	C22—C23—H23	119.9
C8—C9—H9	120.1	C24—C23—H23	119.9
C9—C10—C11	121.3 (4)	N2—C24—C23	124.4 (5)
C9—C10—H10	119.4	N2—C24—H24	117.8
C11—C10—H10	119.4	C23—C24—H24	117.8
C12—C11—C10	119.2 (4)	C26—C25—C18	122.0 (5)
C12—C11—H11	120.4	C26—C25—H25	119.0
C10—C11—H11	120.4	C18—C25—H25	119.0
C11—C12—C13	120.3 (5)	C25—C26—C21	120.8 (5)
C11—C12—H12	119.8	C25—C26—H26	119.6
C13—C12—H12	119.8	C21—C26—H26	119.6
C8—C13—C12	120.0 (4)

O2—C1—C2—C3	47.2 (6)	C12—C13—C14—O3	−123.8 (4)
O1—C1—C2—C3	−130.0 (4)	C19—N1—C15—C16	−0.1 (6)
O2—C1—C2—C7	−134.7 (5)	N1—C15—C16—C17	−1.3 (7)
O1—C1—C2—C7	48.1 (6)	C15—C16—C17—C18	0.8 (7)
C7—C2—C3—C4	−0.8 (7)	C16—C17—C18—C19	0.9 (6)
C1—C2—C3—C4	177.4 (4)	C16—C17—C18—C25	−179.0 (4)
C2—C3—C4—C5	1.3 (7)	C15—N1—C19—C18	1.9 (6)
C3—C4—C5—C6	0.1 (7)	C15—N1—C19—C20	178.3 (4)
C4—C5—C6—C7	−2.2 (7)	C17—C18—C19—N1	−2.2 (6)
C5—C6—C7—C2	2.7 (7)	C25—C18—C19—N1	177.7 (4)
C5—C6—C7—C8	179.9 (4)	C17—C18—C19—C20	−178.7 (4)
C3—C2—C7—C6	−1.2 (6)	C25—C18—C19—C20	1.2 (6)
C1—C2—C7—C6	−179.4 (4)	C24—N2—C20—C21	1.4 (6)
C3—C2—C7—C8	−178.2 (4)	C24—N2—C20—C19	−177.9 (4)
C1—C2—C7—C8	3.7 (6)	N1—C19—C20—N2	1.9 (6)
C6—C7—C8—C13	84.8 (5)	C18—C19—C20—N2	178.4 (4)
C2—C7—C8—C13	−98.2 (5)	N1—C19—C20—C21	−177.4 (4)
C6—C7—C8—C9	−88.3 (5)	C18—C19—C20—C21	−0.9 (6)
C2—C7—C8—C9	88.7 (5)	N2—C20—C21—C22	−1.2 (7)
C13—C8—C9—C10	1.1 (6)	C19—C20—C21—C22	178.1 (4)
C7—C8—C9—C10	174.3 (4)	N2—C20—C21—C26	−178.5 (4)
C8—C9—C10—C11	−3.2 (7)	C19—C20—C21—C26	0.8 (6)
C9—C10—C11—C12	2.8 (7)	C20—C21—C22—C23	0.0 (7)
C10—C11—C12—C13	−0.1 (7)	C26—C21—C22—C23	177.2 (5)
C9—C8—C13—C12	1.5 (6)	C21—C22—C23—C24	0.9 (8)
C7—C8—C13—C12	−171.6 (4)	C20—N2—C24—C23	−0.4 (7)
C9—C8—C13—C14	−177.7 (4)	C22—C23—C24—N2	−0.7 (8)
C7—C8—C13—C14	9.2 (6)	C17—C18—C25—C26	178.5 (4)
C11—C12—C13—C8	−2.0 (6)	C19—C18—C25—C26	−1.4 (7)
C11—C12—C13—C14	177.2 (4)	C18—C25—C26—C21	1.3 (7)
C8—C13—C14—O4	−124.9 (5)	C20—C21—C26—C25	−1.0 (7)
C12—C13—C14—O4	55.9 (6)	C22—C21—C26—C25	−178.2 (5)
C8—C13—C14—O3	55.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.82	2.643 (4)	161
O3—H3···O1	0.82	1.75	2.559 (4)	172

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₁₄H₉O₄⁻
M_r	422.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.1661 (13), 7.389 (1), 22.160 (2)
β (°)	91.061 (1)
V (Å³)	1991.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.45 × 0.37

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.955, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	9415, 3479, 1771
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.243, 1.01
No. of reflections	3479
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

O1—C1	1.274 (5)	O3—C14	1.315 (5)
O2—C1	1.221 (5)	O4—C14	1.197 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.82	2.643 (4)	160.8
O3—H3···O1	0.82	1.75	2.559 (4)	171.8

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

The author gratefully acknowledges the financial support of the Research Fund of Beijing University of Civil Engineering and Architecture, the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of the Beijing Municipality.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gao, H.-W. & Cheng, P. (2004). Chin. J. Inorg. Chem. 20, 1145–1149. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar