1,3-Di-4-pyridylpropane–4,4′-oxy­dibenzoic acid (1/1)

Li, G.; Salim, C.; Hinode, H.

doi:10.1107/S160053680803331X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2251

doi:10.1107/S160053680803331X

Open

access

1,3-Di-4-pyridylpropane–4,4′-oxydibenzoic acid (1/1)

Guangzhe Li,^a Chris Salim ^a and Hirofumi Hinode ^a ^*

^aDepartment of International Development Engineering, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8550, Japan
^*Correspondence e-mail: HirofumiHinode@yahoo.com

(Received 2 September 2008; accepted 14 October 2008; online 8 November 2008)

The hydrothermal reaction of Cd(NO₃)₂·4H₂O, 1,3-di-4-pyridylpropane (BPP) and 4,4′-oxydibenzoic acid (OBA) led to the formation of the title compound, C₁₃H₁₄N₂·C₁₄H₁₀O₅. The asymmetric unit consists of one molecule of OBA and one of BPP. In the OBA molecule, one COOH group is nearly planar with its attached benzene ring [dihedral angle = 0.9 (1)°], while the other COOH group is slightly twisted with a dihedral angle of 10.8 (3)°. The carboxyl groups form strong intermolecular O—H⋯N hydrogen bonds with N atoms of the pyridine rings in BPP, linking the molecules into zigzag chains.

Related literature

For general background see: Belcher et al. (2002 ); Hagrman et al. (1999 ); Han et al. (2007 ); Luan et al. (2005 ); Nguyen et al. (2006 ); Wang et al. (2005 ); Yaghi et al. (1998 ). For related structures, see: Dai et al. (2005 ); Ma et al. (2006 ); Hou et al. (2008 ); Lee et al. (2003 ); Wang et al. (2008 ); Najafpour et al. (2008 ). For an idependent determination of this structure, see: Dong et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₄N₂·C₁₄H₁₀O₅
M_r = 456.48
Triclinic, $[P \overline 1]$
a = 6.8938 (3) Å
b = 11.5869 (6) Å
c = 14.9570 (9) Å
α = 86.493 (4)°
β = 81.157 (4)°
γ = 74.016 (3)°
V = 1134.67 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.47 × 0.45 × 0.45 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.957, T_max = 0.962
8404 measured reflections
5645 independent reflections
2932 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.147
S = 1.01
5645 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1ⁱ	0.82	1.78	2.598 (2)	174
O5—H5⋯N2ⁱⁱ	0.82	1.87	2.685 (2)	177
Symmetry codes: (i) x+1, y, z; (ii) x-1, y-1, z-1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXS97; software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803331X/fl2221sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803331X/fl2221Isup2.hkl

checkCIF report

Comment top

Over the past decades, the rational design and synthesis of metal-organic frameworks have received extensive attention in the fields of supramolecular chemistry and crystal engineering (Hagrman et al., 1999; Yaghi et al., 1998). These materials exhibit interesting functions such as catalysis, biology, electrical conductivity, magnetism and photochemistry. In the past five years, there has been a growing interest in metal-organic frameworks based on 1,3-di-4-pyridylpropane and 4,4'-oxydibenzoic acid ligands (Wang et al., 2005; Luan et al., 2005; Belcher et al., 2002; Han et al., 2007; Nguyen et al., 2006). Recently, we have focused on preparing metal-organic frameworks containing such organic ligands and metal ions. During the process, a new cocrystal of 1,3-di-4-pyridylpropane and 4,4'-oxydibenzoic acid was obtained which assembled by H-bondin and we report its synthesis and crystal structure here. The structures of some similar molecular materials have been reported (Dai et al., 2005; Lee et al., 2003; Ma et al., 2006; Wang et al., 2008; Hou et al., 2008; Najafpour et al., 2008). An independent study of (I) has also been published (Dong et al., 2008).

As shown in Fig. 1, the asymmetric unit contains one 1,3-di-4-pyridylpropane molecule and one 4,4'-oxydibenzoic acid molecule. The bond lengths and angles are within normal ranges. In 4,4'-oxydibenzoic acid molecule, one COOH group (C7/O2/O3) is nearly planar with one benzene ring (C1/C2/C3/C4/C5/C6, dihedral angle of 0.9 °), while another COOH group (C14/O4/O5) has a dihedral angle of 10.8 ° with another benzene ring (C8/C9/C10/C11/C12/C13). The dihedral angle between two benzene ring of a 4,4'-oxydibenzoic acid molecule is 57.0 °. In 1,3-di-4-pyridylpropane molecule, the dihedral angle between two pyridyl rings is 26.9 °. The carboxylic acid groups form strong intermolecular O—H···N hydrogen bonds (Table 1) with N atoms of the pyriding rings, linking the molecules into one-dimensional zigzag chains (Fig.2). Intermolecular C—H···O hydrogen bonds may be effective in the stabilization of the crystal structure.

Related literature top

For general background see: Belcher et al. (2002); Hagrman et al. (1999); Han et al. (2007); Luan et al. (2005); Nguyen et al. (2006); Wang et al. (2005); Yaghi et al. (1998). For related structures, see: Dai et al. (2005); Ma et al. (2006); Hou et al. (2008); Lee et al. (2003); Wang et al. (2008); Najafpour et al. (2008). For an idependent determination of this structure, see: Dong et al. (2008).

Experimental top

In a typical synthesis for the title compound, a mixture of Cd(NO₃)₂.4H₂O 120 mg, 4,4'-oxydibenzoic acid 52 mg, 1,3-bis(4-pyridyl)propane 20 mg, HCl (38%) 0.1 ml, NH₃.H₂O 0.08 ml, N,N-dimethylformamide (DMF) 3.0 ml and H₂O 6.0 ml were sealed in a 15 ml Teflon-lined stainless steel autoclave and heated under autogenous pressure for five days at 393 K. After slow cooling to room temperature, the block-shaped colourless crystalline product was filtered, washed with distilled water, and dried at ambient temperature. The crystal used for data collection was obtained directly from the sample that was washed and dried without further re-crystallization.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXS97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A one-dimensional zigzag chain formed by intermolecular O—H···N hydrogen bonds. (Hydrogen bonds are indicated by dashed lines)

1,3-Di-4-pyridylpropane–4,4'-oxydibenzoic acid (1/1) top

Crystal data top

C₁₃H₁₄N₂·C₁₄H₁₀O₅	Z = 2
M_r = 456.48	F(000) = 480
Triclinic, P1	D_x = 1.336 Mg m⁻³
Hall symbol: -P1	Melting point: not measured K
a = 6.8938 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5869 (6) Å	Cell parameters from 5645 reflections
c = 14.9570 (9) Å	θ = 1.8–28.4°
α = 86.493 (4)°	µ = 0.09 mm⁻¹
β = 81.157 (4)°	T = 298 K
γ = 74.016 (3)°	Block, colourless
V = 1134.67 (10) Å³	0.47 × 0.45 × 0.45 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5645 independent reflections
Radiation source: fine-focus sealed tube	2932 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 9.00cm pixels mm^-1	θ_max = 28.4°, θ_min = 1.8°
ϕ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −14→15
T_min = 0.957, T_max = 0.962	l = −19→16
8404 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0616P)² + 0.0668P] where P = (F_o² + 2F_c²)/3
5645 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₃H₁₄N₂·C₁₄H₁₀O₅	γ = 74.016 (3)°
M_r = 456.48	V = 1134.67 (10) Å³
Triclinic, P1	Z = 2
a = 6.8938 (3) Å	Mo Kα radiation
b = 11.5869 (6) Å	µ = 0.09 mm⁻¹
c = 14.9570 (9) Å	T = 298 K
α = 86.493 (4)°	0.47 × 0.45 × 0.45 mm
β = 81.157 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5645 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2932 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.962	R_int = 0.022
8404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
5645 reflections	Δρ_min = −0.28 e Å⁻³
307 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	−0.1086 (2)	0.38623 (14)	0.57527 (11)	0.0497 (4)
N2	0.6799 (2)	0.69499 (14)	0.97352 (11)	0.0497 (4)
C15	0.0705 (3)	0.38146 (18)	0.59963 (16)	0.0580 (6)
H15	0.1800	0.3156	0.5827	0.080*
C16	0.1014 (3)	0.46960 (19)	0.64881 (16)	0.0571 (6)
H16	0.2301	0.4623	0.6640	0.080*
C17	−0.0570 (3)	0.56910 (16)	0.67593 (13)	0.0427 (5)
C18	−0.2430 (3)	0.57321 (17)	0.64994 (14)	0.0488 (5)
H18	−0.3553	0.6379	0.6662	0.080*
C19	−0.2627 (3)	0.48237 (19)	0.60034 (15)	0.0527 (5)
H19	−0.3893	0.4879	0.5834	0.080*
C20	−0.0312 (3)	0.67052 (17)	0.72756 (14)	0.0508 (5)
H20A	−0.1531	0.6990	0.7709	0.080*
H20B	−0.0205	0.7362	0.6854	0.080*
C21	0.1517 (3)	0.63922 (18)	0.77781 (15)	0.0541 (5)
H21A	0.1416	0.5743	0.8209	0.080*
H21B	0.2747	0.6112	0.7350	0.080*
C22	0.1678 (3)	0.74500 (17)	0.82751 (15)	0.0538 (5)
H22A	0.0454	0.7708	0.8710	0.080*
H22B	0.1703	0.8106	0.7842	0.080*
C23	0.6401 (3)	0.60151 (18)	0.93963 (15)	0.0564 (6)
H23	0.7250	0.5252	0.9483	0.080*
C24	0.4788 (3)	0.61262 (17)	0.89228 (15)	0.0539 (6)
H24	0.4566	0.5445	0.8705	0.080*
C25	0.3504 (3)	0.72434 (17)	0.87710 (13)	0.0437 (5)
C26	0.3944 (3)	0.82112 (17)	0.91119 (15)	0.0504 (5)
H26	0.3140	0.8986	0.9022	0.080*
C27	0.5568 (3)	0.80294 (18)	0.95832 (15)	0.0528 (5)
H27	0.5821	0.8696	0.9808	0.080*
O1	0.6084 (2)	−0.16655 (12)	0.27513 (10)	0.0580 (4)
O2	0.5302 (2)	0.29158 (14)	0.50942 (13)	0.0798 (6)
O3	0.8616 (2)	0.20798 (13)	0.48596 (12)	0.0716 (5)
H3	0.8631	0.2642	0.5163	0.080*
O4	−0.1236 (2)	−0.11337 (12)	0.04949 (11)	0.0666 (5)
O5	−0.0307 (2)	−0.31076 (12)	0.07640 (11)	0.0603 (4)
H5	−0.1219	−0.3094	0.0467	0.080*
C1	0.6118 (3)	−0.06807 (16)	0.32224 (13)	0.0440 (5)
C2	0.4410 (3)	0.01727 (18)	0.35955 (14)	0.0496 (5)
H2	0.3120	0.0137	0.3510	0.080*
C3	0.4625 (3)	0.10781 (17)	0.40961 (14)	0.0477 (5)
H3A	0.3471	0.1655	0.4346	0.080*
C4	0.6537 (3)	0.11418 (16)	0.42333 (13)	0.0412 (4)
C5	0.8235 (3)	0.02569 (18)	0.38713 (14)	0.0487 (5)
H5A	0.9524	0.0275	0.3972	0.080*
C6	0.8041 (3)	−0.06484 (17)	0.33646 (14)	0.0500 (5)
H6	0.9190	−0.1232	0.3120	0.080*
C7	0.6739 (3)	0.21355 (17)	0.47726 (14)	0.0481 (5)
C8	0.4451 (3)	−0.16717 (17)	0.23154 (13)	0.0454 (5)
C9	0.3450 (3)	−0.07097 (17)	0.18192 (14)	0.0519 (5)
H9	0.3782	0.0018	0.1802	0.080*
C10	0.1958 (3)	−0.08367 (16)	0.13509 (14)	0.0486 (5)
H10	0.1277	−0.0188	0.1019	0.080*
C11	0.1450 (3)	−0.19174 (16)	0.13651 (13)	0.0408 (4)
C12	0.2458 (3)	−0.28742 (16)	0.18693 (14)	0.0481 (5)
H12	0.2126	−0.3602	0.1889	0.080*
C13	0.3958 (3)	−0.27513 (17)	0.23433 (15)	0.0513 (5)
H13	0.4635	−0.3396	0.2681	0.080*
C14	−0.0170 (3)	−0.20004 (17)	0.08383 (13)	0.0442 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0480 (10)	0.0533 (10)	0.0517 (11)	−0.0151 (8)	−0.0135 (8)	−0.0097 (8)
N2	0.0498 (10)	0.0505 (10)	0.0547 (11)	−0.0163 (8)	−0.0186 (8)	−0.0058 (8)
C15	0.0486 (12)	0.0560 (13)	0.0700 (16)	−0.0095 (10)	−0.0119 (11)	−0.0195 (11)
C16	0.0407 (11)	0.0625 (13)	0.0725 (15)	−0.0109 (10)	−0.0191 (10)	−0.0214 (11)
C17	0.0419 (10)	0.0467 (11)	0.0425 (11)	−0.0126 (9)	−0.0128 (9)	−0.0054 (8)
C18	0.0422 (11)	0.0497 (11)	0.0563 (13)	−0.0094 (9)	−0.0166 (10)	−0.0059 (9)
C19	0.0462 (11)	0.0579 (13)	0.0600 (14)	−0.0157 (10)	−0.0210 (10)	−0.0052 (10)
C20	0.0483 (11)	0.0509 (12)	0.0578 (13)	−0.0129 (9)	−0.0184 (10)	−0.0124 (10)
C21	0.0516 (12)	0.0544 (12)	0.0625 (14)	−0.0151 (10)	−0.0207 (10)	−0.0132 (10)
C22	0.0558 (12)	0.0519 (12)	0.0594 (14)	−0.0136 (10)	−0.0236 (10)	−0.0101 (10)
C23	0.0604 (13)	0.0476 (12)	0.0682 (15)	−0.0155 (10)	−0.0284 (11)	−0.0020 (10)
C24	0.0617 (13)	0.0434 (11)	0.0655 (15)	−0.0189 (10)	−0.0251 (11)	−0.0083 (10)
C25	0.0470 (11)	0.0456 (11)	0.0423 (11)	−0.0156 (9)	−0.0111 (9)	−0.0052 (8)
C26	0.0489 (11)	0.0431 (11)	0.0625 (14)	−0.0116 (9)	−0.0165 (10)	−0.0099 (9)
C27	0.0516 (12)	0.0496 (12)	0.0635 (14)	−0.0171 (10)	−0.0155 (10)	−0.0157 (10)
O1	0.0535 (8)	0.0512 (8)	0.0755 (11)	−0.0093 (6)	−0.0305 (7)	−0.0179 (7)
O2	0.0523 (9)	0.0721 (11)	0.1135 (15)	0.0026 (8)	−0.0246 (9)	−0.0481 (10)
O3	0.0488 (9)	0.0740 (10)	0.0991 (13)	−0.0148 (7)	−0.0181 (8)	−0.0448 (9)
O4	0.0742 (10)	0.0471 (8)	0.0893 (12)	−0.0147 (7)	−0.0498 (9)	0.0038 (8)
O5	0.0661 (9)	0.0437 (8)	0.0821 (11)	−0.0164 (7)	−0.0396 (8)	−0.0061 (7)
C1	0.0472 (11)	0.0451 (11)	0.0449 (12)	−0.0148 (9)	−0.0160 (9)	−0.0064 (8)
C2	0.0375 (10)	0.0591 (12)	0.0571 (13)	−0.0141 (9)	−0.0171 (9)	−0.0078 (10)
C3	0.0368 (10)	0.0536 (12)	0.0527 (13)	−0.0070 (9)	−0.0124 (9)	−0.0098 (9)
C4	0.0405 (10)	0.0450 (10)	0.0398 (11)	−0.0110 (8)	−0.0104 (8)	−0.0057 (8)
C5	0.0359 (10)	0.0578 (12)	0.0559 (13)	−0.0147 (9)	−0.0084 (9)	−0.0147 (10)
C6	0.0392 (10)	0.0552 (12)	0.0563 (13)	−0.0104 (9)	−0.0074 (9)	−0.0156 (10)
C7	0.0460 (11)	0.0496 (12)	0.0513 (13)	−0.0100 (10)	−0.0171 (10)	−0.0086 (9)
C8	0.0463 (11)	0.0472 (11)	0.0471 (12)	−0.0127 (9)	−0.0166 (9)	−0.0089 (9)
C9	0.0659 (13)	0.0433 (11)	0.0557 (13)	−0.0234 (10)	−0.0220 (11)	0.0014 (9)
C10	0.0596 (12)	0.0423 (11)	0.0493 (12)	−0.0155 (9)	−0.0212 (10)	0.0001 (9)
C11	0.0438 (10)	0.0393 (10)	0.0418 (11)	−0.0115 (8)	−0.0109 (9)	−0.0059 (8)
C12	0.0533 (11)	0.0383 (10)	0.0581 (13)	−0.0142 (9)	−0.0199 (10)	−0.0021 (9)
C13	0.0551 (12)	0.0412 (11)	0.0613 (14)	−0.0104 (9)	−0.0256 (10)	0.0009 (9)
C14	0.0453 (11)	0.0411 (11)	0.0484 (12)	−0.0112 (9)	−0.0118 (9)	−0.0071 (9)

Geometric parameters (Å, º) top

N1—C15	1.326 (2)	O1—C1	1.385 (2)
N1—C19	1.337 (2)	O1—C8	1.387 (2)
N2—C27	1.333 (2)	O2—C7	1.202 (2)
N2—C23	1.334 (2)	O3—C7	1.304 (2)
C15—C16	1.375 (3)	O3—H3	0.8200
C15—H15	0.9300	O4—C14	1.208 (2)
C16—C17	1.383 (3)	O5—C14	1.325 (2)
C16—H16	0.9300	O5—H5	0.8200
C17—C18	1.384 (2)	C1—C2	1.379 (3)
C17—C20	1.509 (2)	C1—C6	1.385 (2)
C18—C19	1.372 (3)	C2—C3	1.378 (3)
C18—H18	0.9300	C2—H2	0.9300
C19—H19	0.9300	C3—C4	1.387 (2)
C20—C21	1.514 (3)	C3—H3A	0.9300
C20—H20A	0.9700	C4—C5	1.388 (2)
C20—H20B	0.9700	C4—C7	1.494 (2)
C21—C22	1.510 (3)	C5—C6	1.378 (2)
C21—H21A	0.9700	C5—H5A	0.9300
C21—H21B	0.9700	C6—H6	0.9300
C22—C25	1.514 (3)	C8—C9	1.379 (3)
C22—H22A	0.9700	C8—C13	1.380 (3)
C22—H22B	0.9700	C9—C10	1.374 (3)
C23—C24	1.381 (3)	C9—H9	0.9300
C23—H23	0.9300	C10—C11	1.388 (2)
C24—C25	1.380 (3)	C10—H10	0.9300
C24—H24	0.9300	C11—C12	1.384 (3)
C25—C26	1.384 (2)	C11—C14	1.489 (2)
C26—C27	1.374 (3)	C12—C13	1.382 (3)
C26—H26	0.9300	C12—H12	0.9300
C27—H27	0.9300	C13—H13	0.9300

C15—N1—C19	117.07 (16)	N2—C27—H27	118.2
C27—N2—C23	116.59 (16)	C26—C27—H27	118.2
N1—C15—C16	122.91 (18)	C1—O1—C8	122.02 (14)
N1—C15—H15	118.5	C7—O3—H3	109.5
C16—C15—H15	118.5	C14—O5—H5	109.5
C15—C16—C17	120.72 (17)	C2—C1—C6	120.44 (16)
C15—C16—H16	119.6	C2—C1—O1	124.67 (16)
C17—C16—H16	119.6	C6—C1—O1	114.70 (16)
C16—C17—C18	115.85 (17)	C3—C2—C1	119.62 (17)
C16—C17—C20	123.19 (16)	C3—C2—H2	120.2
C18—C17—C20	120.92 (16)	C1—C2—H2	120.2
C19—C18—C17	120.35 (17)	C2—C3—C4	120.95 (17)
C19—C18—H18	119.8	C2—C3—H3A	119.5
C17—C18—H18	119.8	C4—C3—H3A	119.5
N1—C19—C18	123.10 (17)	C3—C4—C5	118.54 (16)
N1—C19—H19	118.4	C3—C4—C7	120.15 (16)
C18—C19—H19	118.4	C5—C4—C7	121.30 (16)
C17—C20—C21	115.27 (16)	C6—C5—C4	121.02 (16)
C17—C20—H20A	108.5	C6—C5—H5A	119.5
C21—C20—H20A	108.5	C4—C5—H5A	119.5
C17—C20—H20B	108.5	C5—C6—C1	119.39 (17)
C21—C20—H20B	108.5	C5—C6—H6	120.3
H20A—C20—H20B	107.5	C1—C6—H6	120.3
C22—C21—C20	112.25 (16)	O2—C7—O3	123.16 (17)
C22—C21—H21A	109.2	O2—C7—C4	122.99 (17)
C20—C21—H21A	109.2	O3—C7—C4	113.85 (16)
C22—C21—H21B	109.2	C9—C8—C13	120.40 (17)
C20—C21—H21B	109.2	C9—C8—O1	123.73 (17)
H21A—C21—H21B	107.9	C13—C8—O1	115.68 (17)
C21—C22—C25	116.41 (17)	C10—C9—C8	119.34 (17)
C21—C22—H22A	108.2	C10—C9—H9	120.3
C25—C22—H22A	108.2	C8—C9—H9	120.3
C21—C22—H22B	108.2	C9—C10—C11	121.15 (18)
C25—C22—H22B	108.2	C9—C10—H10	119.4
H22A—C22—H22B	107.3	C11—C10—H10	119.4
N2—C23—C24	123.12 (18)	C12—C11—C10	118.96 (17)
N2—C23—H23	118.4	C12—C11—C14	122.47 (17)
C24—C23—H23	118.4	C10—C11—C14	118.57 (17)
C25—C24—C23	120.29 (17)	C13—C12—C11	120.16 (17)
C25—C24—H24	119.9	C13—C12—H12	119.9
C23—C24—H24	119.9	C11—C12—H12	119.9
C24—C25—C26	116.32 (17)	C8—C13—C12	119.99 (18)
C24—C25—C22	124.00 (16)	C8—C13—H13	120.0
C26—C25—C22	119.67 (17)	C12—C13—H13	120.0
C27—C26—C25	120.08 (18)	O4—C14—O5	123.14 (17)
C27—C26—H26	120.0	O4—C14—C11	122.70 (17)
C25—C26—H26	120.0	O5—C14—C11	114.15 (16)
N2—C27—C26	123.58 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1ⁱ	0.82	1.78	2.598 (2)	174.0
O5—H5···N2ⁱⁱ	0.82	1.87	2.685 (2)	176.9

Symmetry codes: (i) x+1, y, z; (ii) x−1, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂·C₁₄H₁₀O₅
M_r	456.48
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.8938 (3), 11.5869 (6), 14.9570 (9)
α, β, γ (°)	86.493 (4), 81.157 (4), 74.016 (3)
V (Å³)	1134.67 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.45 × 0.45

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.957, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	8404, 5645, 2932
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.147, 1.01
No. of reflections	5645
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.28

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1ⁱ	0.82	1.78	2.598 (2)	174.0
O5—H5···N2ⁱⁱ	0.82	1.87	2.685 (2)	176.9

Symmetry codes: (i) x+1, y, z; (ii) x−1, y−1, z−1.

Acknowledgements

The authors thank Tokyo Institute of Technology and MEXT for the financial support of this work.

References

Belcher, W. J., Longstaff, C. A., Neckenig, M. R. & Steed, J. W. (2002). Chem. Commun. pp. 1602–1603. Web of Science CSD CrossRef Google Scholar
Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dai, Y.-M., Shen, H.-Y. & Huang, J.-F. (2005). Acta Cryst. E61, o3410–o3411. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, W.-W., Li, D.-S., Zhao, J., Tang, L. & Hou, X.-Y. (2008). Acta Cryst. E64, o2252. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hagrman, P. J., Hagrman, D. & Zubieta, J. (1999). Angew. Chem. Int. Ed. 38, 2638–2684. CrossRef Google Scholar
Han, L., Valle, H. & Bu, X. H. (2007). Inorg. Chem. 46, 1511–1513. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hou, G.-G., Liu, L.-L., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2008). Acta Cryst. E64, o997. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lee, T. W., Lau, J. P. K. & Szeto, L. (2003). Acta Cryst. E59, o792–o793. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luan, X. J., Wang, Y. Y., Li, D. S., Liu, P., Hu, H. M., Shi, Q. Z. & Peng, S. M. (2005). Angew. Chem. Int. Ed. 44, 3864–3867. Web of Science CSD CrossRef CAS Google Scholar
Ma, Z.-C., Ma, A.-Q. & Wang, G.-P. (2006). Acta Cryst. E62, o1165–o1166. Web of Science CSD CrossRef IUCr Journals Google Scholar
Najafpour, M. M., Hołyńska, M. & Lis, T. (2008). Acta Cryst. E64, o985. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nguyen, D. T., Chew, E., Zhang, Q. C., Choi, A. & Bu, X. H. (2006). Inorg. Chem. 45, 10722–10727. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-Y., Hu, R.-D. & Wang, Y.-J. (2008). Acta Cryst. E64, o1442. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, X. L., Qin, C., Wang, E. B., Li, Y. G., Su, Z. M. & Carlucci, L. (2005). Angew. Chem. Int. Ed. 44, 5824–5827. Web of Science CSD CrossRef CAS Google Scholar
Yaghi, O. M., Li, H., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474–484. Web of Science CrossRef CAS Google Scholar