4,4′-Bipyrid­yl–4,4′-(hy­droxy­methyl­ene)dibenzoic acid (1/1)

Qin, L.; Xu, L.-P.; Han, L.

doi:10.1107/S1600536812011956

organic compounds

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Volume 68| Part 4| April 2012| Page o1175

doi:10.1107/S1600536812011956

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4,4′-Bipyridyl–4,4′-(hydroxymethylene)dibenzoic acid (1/1)

Lan Qin,^a Lan-Ping Xu ^a and Lei Han ^a ^*

^aFaculty of Materials Science & Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: hanlei@nbu.edu.cn

(Received 19 March 2012; accepted 20 March 2012; online 24 March 2012)

In the title 1:1 co-crystal, C₁₀H₈N₂·C₁₅H₁₂O₅, strong intermolecular O—H⋯N hydrogen bonds link alternating molecules of 4,4′-(hydroxymethylene)dibenzoic acid and 4,4′-bipyridyl into zigzag chains in [501]. The crystal packing also exhibits π–π interactions between the 4,4′-bipyridyl rings of neighbouring chains [centroid–centroid distance = 3.608 (3) Å] and weak C—H⋯O hydrogen bonds.

Related literature

For background to supramolecular crystal engineering, see: Simon & Bassoul (2000 ). For aromatic carboxylic acids as supramolecular synthons, see: Desiraju (1995 ). For studies of bent arenedicarboxylate ligands, see: Koichi et al. (2011 ); Xu et al. (2011 ).

Experimental

Crystal data

C₁₀H₈N₂·C₁₅H₁₂O₅
M_r = 428.43
Monoclinic, P 2₁ /n
a = 8.0528 (16) Å
b = 11.683 (2) Å
c = 21.922 (4) Å
β = 96.66 (3)°
V = 2048.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.31 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.984, T_max = 0.988
16322 measured reflections
3800 independent reflections
1903 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.210
S = 0.99
3800 reflections
298 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 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
O2—H2⋯N2ⁱ	0.84 (5)	1.82 (5)	2.660 (5)	173 (5)
O4—H1⋯N1ⁱⁱ	0.87 (6)	1.76 (6)	2.605 (5)	166 (5)
C19—H19A⋯O3ⁱⁱⁱ	0.93	2.40	3.321 (5)	171
C17—H17A⋯O1^iv	0.93	2.57	3.212 (5)	126
C8—H8A⋯O3^iv	0.98	2.51	3.376 (6)	148
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) -x+1, -y, -z; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812011956/cv5265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011956/cv5265Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812011956/cv5265Isup3.cml

checkCIF report

Comment top

Supramolecular crystal engineering has attracted growing interest over the past few decades because of their importance in biological system and molecular recognition (Simon et al., 2000). Aromatic carboxylic acid is one of the most important supramolecular synthons to construct novel organic networks by hydrogen bonds and π–π interactions (Desiraju, 1995). Recently, interest has been devoted to the assembly of extended solids from the long and bent arenedicarboxylate ligands (Koichi et al., 2011; Xu et al., 2011). We have employed 4,4'-(hydroxymethylene)dibenzoic acid as an excellent candidate for the construction of targeted supramolecular structures. A new organic cocrystal compound, C₁₅H₁₂O₅.C₁₀H₈N₂, has been synthesized by reacting 4,4'-(hydroxymethylene)dibenzoic acid and 4,4'-bipyridyl under hydrothermal conditions, and its crystal structure is reported here.

The asymmetric unit of the title compound consists of one 4,4'-(hydroxymethylene)dibenzoic acid and one 4,4'-bipyridyl molecule (Figure 1). The dihedral angle formed by two pyridine rings in 4,4'-bipyridyl is 24.74 (1)° , and the dihedral angle between the two benzene rings in bent 4,4'-(hydroxymethylene)dibenzoic acid ligand is 85.95 (3)° . In the1:1 cocrystal, strong intermolecular O—H···N hydrogen bonds link the alternating molecules of 4,4'-(hydroxymethylene)dibenzoic acid and 4,4'-bipyridyl into zigzag chains in [501], as shown in Figure 2. Furthermore, the crystal packing exhibits also π–π interactions between the rings of 4,4'-bipyridyl from the neighbouring chains [centroid–centroid distance of 3.608 (3) Å] and weak C—H···O hydrogen bonds.

Related literature top

For background to supramolecular crystal engineering, see: Simon & Bassoul (2000). For aromatic carboxylic acid as a supramolecular synthon, see: Desiraju (1995). For studies of bent arenedicarboxylate ligands, see: Koichi et al. (2011); Xu et al. (2011).

Experimental top

A mixture of 4,4'-(hydroxymethylene)dibenzoic acid (26.4 mg, 0.1 mmol) and 4,4'-bipyridyl (15.1 mg, 0.1 mmol) in H₂O (8 ml) was sealed in a 25 ml Teflon-lined stainless steel reactor and heated at 447 K for 3 d. Colorless single crystals of the title compound was obtained after cooling the solution to room temperature. Block-shaped crystals were collected and washed with distilled water. The yield was approximately 70% based on 4,4'-(hydroxymethylene)dibenzoic acid.

Structure description top

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A content of asymmetric unit of the title compound showing the atomic numbering and 30% probability displacement ellipsoids.
	Fig. 2. A portion of the crystal packing showing O—H···N hydrogen bonds as dashed lines.

4,4'-Bipyridyl–4,4'-(hydroxymethylene)dibenzoic acid (1/1) top

Crystal data top

C₁₀H₈N₂·C₁₅H₁₂O₅	F(000) = 896
M_r = 428.43	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2687 reflections
a = 8.0528 (16) Å	θ = 3.1–25.5°
b = 11.683 (2) Å	µ = 0.10 mm⁻¹
c = 21.922 (4) Å	T = 298 K
β = 96.66 (3)°	Block, colourless
V = 2048.6 (7) Å³	0.31 × 0.14 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3800 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
T_min = 0.984, T_max = 0.988	l = −26→24
16322 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.077	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.210	w = 1/[σ²(F_o²) + (0.0824P)² + 1.4919P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3800 reflections	Δρ_max = 0.68 e Å⁻³
298 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (18)

Crystal data top

C₁₀H₈N₂·C₁₅H₁₂O₅	V = 2048.6 (7) Å³
M_r = 428.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0528 (16) Å	µ = 0.10 mm⁻¹
b = 11.683 (2) Å	T = 298 K
c = 21.922 (4) Å	0.31 × 0.14 × 0.12 mm
β = 96.66 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3800 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1903 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.988	R_int = 0.089
16322 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.68 e Å⁻³
3800 reflections	Δρ_min = −0.28 e Å⁻³
298 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.7007 (4)	−0.0589 (3)	0.44854 (15)	0.0828 (10)
O2	1.8293 (4)	−0.0048 (3)	0.36999 (15)	0.0844 (11)
O3	0.6425 (4)	−0.0831 (3)	0.12982 (16)	0.0831 (10)
O4	0.5017 (4)	0.0793 (3)	0.11948 (17)	0.0863 (12)
O5	1.1910 (4)	0.3660 (3)	0.2676 (2)	0.1155 (15)
H5A	1.1098	0.4045	0.2542	0.173*
N1	−0.2656 (4)	0.0472 (3)	−0.06295 (16)	0.0628 (10)
N2	0.4192 (4)	0.3635 (3)	0.08219 (19)	0.0694 (10)
C1	1.7018 (5)	−0.0067 (4)	0.4015 (2)	0.0610 (11)
C2	1.5595 (5)	0.0650 (4)	0.37421 (18)	0.0557 (11)
C3	1.5610 (5)	0.1201 (4)	0.31932 (19)	0.0686 (13)
H3A	1.6546	0.1139	0.2984	0.082*
C4	1.4188 (5)	0.0754 (4)	0.40432 (19)	0.0633 (12)
H4A	1.4142	0.0385	0.4417	0.076*
C5	1.4258 (5)	0.1850 (5)	0.2941 (2)	0.0780 (15)
H5B	1.4302	0.2220	0.2568	0.094*
C6	1.2844 (5)	0.1406 (4)	0.3790 (2)	0.0668 (12)
H6A	1.1908	0.1475	0.3999	0.080*
C7	1.2865 (5)	0.1952 (4)	0.3238 (2)	0.0653 (12)
C8	1.1347 (5)	0.2650 (4)	0.2987 (2)	0.0784 (15)
H8A	1.0768	0.2904	0.3332	0.094*
C9	1.0110 (4)	0.1983 (4)	0.25372 (18)	0.0586 (11)
C10	1.0175 (5)	0.0821 (4)	0.24747 (19)	0.0660 (12)
H10A	1.1054	0.0415	0.2686	0.079*
C11	0.8944 (5)	0.0235 (4)	0.20995 (19)	0.0613 (11)
H11A	0.9000	−0.0557	0.2064	0.074*
C12	0.7646 (4)	0.0829 (4)	0.17821 (17)	0.0526 (10)
C13	0.7589 (5)	0.1998 (4)	0.18338 (18)	0.0608 (11)
H13A	0.6723	0.2404	0.1614	0.073*
C14	0.8806 (5)	0.2575 (4)	0.22089 (19)	0.0618 (11)
H14A	0.8752	0.3368	0.2242	0.074*
C15	0.6312 (5)	0.0179 (4)	0.1404 (2)	0.0616 (11)
C16	−0.2813 (5)	0.1129 (4)	−0.0146 (2)	0.0671 (12)
H16A	−0.3849	0.1154	0.0003	0.081*
C17	−0.1537 (5)	0.1778 (4)	0.01501 (19)	0.0594 (11)
H17A	−0.1712	0.2220	0.0489	0.071*
C18	0.0024 (4)	0.1760 (3)	−0.00674 (18)	0.0515 (10)
C19	0.0182 (5)	0.1095 (3)	−0.05812 (18)	0.0578 (11)
H19A	0.1191	0.1070	−0.0748	0.069*
C20	−0.1179 (5)	0.0466 (4)	−0.0844 (2)	0.0641 (12)
H20A	−0.1051	0.0020	−0.1187	0.077*
C21	0.1463 (5)	0.2406 (3)	0.02397 (18)	0.0526 (10)
C22	0.1556 (5)	0.2692 (4)	0.0859 (2)	0.0649 (12)
H22A	0.0711	0.2478	0.1091	0.078*
C23	0.2930 (5)	0.3303 (4)	0.1123 (2)	0.0725 (13)
H23A	0.2973	0.3492	0.1536	0.087*
C24	0.4097 (5)	0.3339 (4)	0.0235 (2)	0.0679 (13)
H24A	0.4970	0.3555	0.0017	0.082*
C25	0.2790 (5)	0.2731 (4)	−0.0073 (2)	0.0631 (12)
H25A	0.2798	0.2542	−0.0484	0.076*
H2	1.915 (6)	−0.042 (5)	0.385 (2)	0.100 (19)*
H1	0.436 (7)	0.031 (5)	0.099 (2)	0.11 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.084 (2)	0.091 (3)	0.071 (2)	0.0073 (18)	0.0029 (17)	0.0258 (19)
O2	0.061 (2)	0.109 (3)	0.082 (2)	0.023 (2)	0.0036 (18)	0.026 (2)
O3	0.0630 (19)	0.078 (3)	0.105 (3)	−0.0035 (17)	−0.0046 (17)	−0.008 (2)
O4	0.062 (2)	0.083 (3)	0.106 (3)	0.0024 (18)	−0.0254 (19)	−0.017 (2)
O5	0.089 (3)	0.090 (3)	0.156 (4)	−0.001 (2)	−0.033 (2)	0.012 (3)
N1	0.053 (2)	0.064 (2)	0.068 (2)	0.0002 (17)	−0.0067 (18)	−0.0012 (19)
N2	0.054 (2)	0.068 (3)	0.083 (3)	−0.0012 (18)	−0.007 (2)	−0.005 (2)
C1	0.057 (3)	0.068 (3)	0.057 (3)	−0.005 (2)	−0.002 (2)	−0.001 (2)
C2	0.051 (2)	0.064 (3)	0.051 (2)	−0.0029 (19)	0.0005 (19)	0.000 (2)
C3	0.053 (2)	0.095 (4)	0.058 (3)	0.014 (2)	0.009 (2)	0.012 (3)
C4	0.066 (3)	0.073 (3)	0.050 (2)	−0.013 (2)	0.007 (2)	−0.004 (2)
C5	0.064 (3)	0.109 (4)	0.060 (3)	0.015 (3)	0.002 (2)	0.015 (3)
C6	0.047 (2)	0.085 (3)	0.070 (3)	−0.001 (2)	0.010 (2)	−0.020 (3)
C7	0.052 (2)	0.079 (3)	0.063 (3)	0.002 (2)	−0.007 (2)	−0.015 (2)
C8	0.063 (3)	0.074 (4)	0.094 (4)	0.007 (2)	−0.011 (3)	−0.014 (3)
C9	0.045 (2)	0.071 (3)	0.059 (2)	0.002 (2)	0.0015 (19)	−0.012 (2)
C10	0.051 (2)	0.077 (3)	0.065 (3)	0.010 (2)	−0.011 (2)	−0.007 (2)
C11	0.058 (2)	0.059 (3)	0.064 (3)	0.005 (2)	0.000 (2)	−0.002 (2)
C12	0.044 (2)	0.064 (3)	0.049 (2)	−0.0003 (19)	0.0033 (17)	0.001 (2)
C13	0.048 (2)	0.074 (3)	0.058 (2)	0.006 (2)	−0.0040 (19)	0.000 (2)
C14	0.056 (2)	0.061 (3)	0.066 (3)	0.003 (2)	−0.001 (2)	−0.003 (2)
C15	0.055 (3)	0.064 (3)	0.065 (3)	0.001 (2)	0.001 (2)	−0.001 (2)
C16	0.047 (2)	0.068 (3)	0.086 (3)	0.001 (2)	0.005 (2)	−0.002 (3)
C17	0.054 (2)	0.061 (3)	0.062 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
C18	0.048 (2)	0.051 (3)	0.053 (2)	0.0009 (18)	−0.0034 (18)	0.005 (2)
C19	0.053 (2)	0.059 (3)	0.059 (3)	0.003 (2)	−0.001 (2)	0.002 (2)
C20	0.063 (3)	0.066 (3)	0.060 (3)	0.003 (2)	−0.005 (2)	−0.003 (2)
C21	0.049 (2)	0.051 (3)	0.055 (2)	0.0005 (18)	−0.0044 (19)	0.0004 (19)
C22	0.056 (2)	0.065 (3)	0.071 (3)	0.000 (2)	−0.006 (2)	−0.004 (2)
C23	0.066 (3)	0.076 (3)	0.071 (3)	0.006 (2)	−0.012 (2)	−0.009 (3)
C24	0.052 (2)	0.070 (3)	0.080 (3)	−0.003 (2)	−0.002 (2)	0.004 (3)
C25	0.057 (2)	0.069 (3)	0.062 (3)	−0.003 (2)	0.000 (2)	0.003 (2)

Geometric parameters (Å, º) top

O1—C1	1.199 (5)	C9—C14	1.387 (5)
O2—C1	1.302 (5)	C10—C11	1.392 (5)
O2—H2	0.84 (5)	C10—H10A	0.9300
O3—C15	1.208 (5)	C11—C12	1.375 (5)
O4—C15	1.304 (5)	C11—H11A	0.9300
O4—H1	0.87 (6)	C12—C13	1.371 (6)
O5—C8	1.460 (6)	C12—C15	1.487 (6)
O5—H5A	0.8200	C13—C14	1.380 (5)
N1—C16	1.327 (5)	C13—H13A	0.9300
N1—C20	1.329 (5)	C14—H14A	0.9300
N2—C24	1.325 (6)	C16—C17	1.377 (5)
N2—C23	1.332 (6)	C16—H16A	0.9300
C1—C2	1.488 (6)	C17—C18	1.395 (5)
C2—C3	1.365 (5)	C17—H17A	0.9300
C2—C4	1.381 (6)	C18—C19	1.386 (5)
C3—C5	1.388 (6)	C18—C21	1.478 (5)
C3—H3A	0.9300	C19—C20	1.387 (5)
C4—C6	1.386 (6)	C19—H19A	0.9300
C4—H4A	0.9300	C20—H20A	0.9300
C5—C7	1.365 (6)	C21—C25	1.387 (6)
C5—H5B	0.9300	C21—C22	1.391 (5)
C6—C7	1.370 (6)	C22—C23	1.385 (6)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.518 (6)	C23—H23A	0.9300
C8—C9	1.531 (6)	C24—C25	1.379 (6)
C8—H8A	0.9800	C24—H24A	0.9300
C9—C10	1.367 (6)	C25—H25A	0.9300

C1—O2—H2	116 (4)	C13—C12—C15	121.7 (4)
C15—O4—H1	104 (4)	C11—C12—C15	118.8 (4)
C8—O5—H5A	109.5	C12—C13—C14	120.5 (4)
C16—N1—C20	117.2 (4)	C12—C13—H13A	119.7
C24—N2—C23	116.3 (4)	C14—C13—H13A	119.7
O1—C1—O2	123.3 (4)	C13—C14—C9	120.5 (4)
O1—C1—C2	123.3 (4)	C13—C14—H14A	119.7
O2—C1—C2	113.3 (4)	C9—C14—H14A	119.7
C3—C2—C4	118.1 (4)	O3—C15—O4	123.0 (4)
C3—C2—C1	122.3 (4)	O3—C15—C12	122.7 (4)
C4—C2—C1	119.6 (4)	O4—C15—C12	114.3 (4)
C2—C3—C5	121.4 (4)	N1—C16—C17	124.0 (4)
C2—C3—H3A	119.3	N1—C16—H16A	118.0
C5—C3—H3A	119.3	C17—C16—H16A	118.0
C2—C4—C6	120.2 (4)	C16—C17—C18	118.9 (4)
C2—C4—H4A	119.9	C16—C17—H17A	120.5
C6—C4—H4A	119.9	C18—C17—H17A	120.5
C7—C5—C3	120.6 (4)	C19—C18—C17	117.2 (4)
C7—C5—H5B	119.7	C19—C18—C21	121.0 (4)
C3—C5—H5B	119.7	C17—C18—C21	121.8 (4)
C7—C6—C4	121.4 (4)	C18—C19—C20	119.5 (4)
C7—C6—H6A	119.3	C18—C19—H19A	120.3
C4—C6—H6A	119.3	C20—C19—H19A	120.3
C5—C7—C6	118.3 (4)	N1—C20—C19	123.1 (4)
C5—C7—C8	123.1 (5)	N1—C20—H20A	118.4
C6—C7—C8	118.5 (4)	C19—C20—H20A	118.4
O5—C8—C7	108.8 (4)	C25—C21—C22	117.3 (4)
O5—C8—C9	108.9 (4)	C25—C21—C18	121.6 (4)
C7—C8—C9	113.3 (4)	C22—C21—C18	121.2 (4)
O5—C8—H8A	108.6	C23—C22—C21	118.8 (4)
C7—C8—H8A	108.6	C23—C22—H22A	120.6
C9—C8—H8A	108.6	C21—C22—H22A	120.6
C10—C9—C14	118.6 (4)	N2—C23—C22	124.1 (5)
C10—C9—C8	122.7 (4)	N2—C23—H23A	117.9
C14—C9—C8	118.5 (4)	C22—C23—H23A	117.9
C9—C10—C11	121.0 (4)	N2—C24—C25	124.3 (4)
C9—C10—H10A	119.5	N2—C24—H24A	117.8
C11—C10—H10A	119.5	C25—C24—H24A	117.8
C12—C11—C10	119.9 (4)	C24—C25—C21	119.2 (4)
C12—C11—H11A	120.1	C24—C25—H25A	120.4
C10—C11—H11A	120.1	C21—C25—H25A	120.4
C13—C12—C11	119.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2ⁱ	0.84 (5)	1.82 (5)	2.660 (5)	173 (5)
O4—H1···N1ⁱⁱ	0.87 (6)	1.76 (6)	2.605 (5)	166 (5)
C19—H19A···O3ⁱⁱⁱ	0.93	2.40	3.321 (5)	171
C17—H17A···O1^iv	0.93	2.57	3.212 (5)	126
C8—H8A···O3^iv	0.98	2.51	3.376 (6)	148

Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·C₁₅H₁₂O₅
M_r	428.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.0528 (16), 11.683 (2), 21.922 (4)
β (°)	96.66 (3)
V (Å³)	2048.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.31 × 0.14 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.984, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	16322, 3800, 1903
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.210, 0.99
No. of reflections	3800
No. of parameters	298
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.28

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), 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
O2—H2···N2ⁱ	0.84 (5)	1.82 (5)	2.660 (5)	173 (5)
O4—H1···N1ⁱⁱ	0.87 (6)	1.76 (6)	2.605 (5)	166 (5)
C19—H19A···O3ⁱⁱⁱ	0.93	2.40	3.321 (5)	171.4
C17—H17A···O1^iv	0.93	2.57	3.212 (5)	126.4
C8—H8A···O3^iv	0.98	2.51	3.376 (6)	147.5

Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21071087) and the K. C. Wong Magna Fund in Ningbo University.

References

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