2-(4-Hydroxy­phen­yl)acetic acid–4,4′-bipyridine (1/1)

Liu, J.-F.; Zhao, G.-L.

doi:10.1107/S1600536810018842

organic compounds

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Volume 66| Part 6| June 2010| Page o1455

https://doi.org/10.1107/S1600536810018842

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2-(4-Hydroxyphenyl)acetic acid–4,4′-bipyridine (1/1)

Jian-Feng Liu ^a and Guo-Liang Zhao ^a ^*

^aCollege of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 10 May 2010; accepted 20 May 2010; online 26 May 2010)

In the acid molecule of the title complex, C₁₀H₈N₂·C₈H₈O₃, the acetyl C—C—C—O torsion angle is −32.1 (3)°, and in the molecule of the base, the dihedral angle between the two pyridine rings is 23.41 (10)°. In the crystal structure, intermolecular O—H⋯N hydrogen bonds link the acid and the base molecules into a one-dimensional triple-helix framework extended along the b axis.

Related literature

For related functional complexes, see: Han et al. (2009 ). For hydrogen-bond motif structures, see: Tomura & Yamashita (2001 ).

Experimental

Crystal data

C₁₀H₈N₂·C₈H₈O₃
M_r = 308.33
Monoclinic, C 2/c
a = 25.3578 (6) Å
b = 10.2305 (2) Å
c = 14.2546 (4) Å
β = 122.321 (2)°
V = 3125.03 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.14 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.984, T_max = 0.994
24334 measured reflections
3650 independent reflections
2128 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.139
S = 1.06
3650 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N2ⁱ	0.97 (2)	1.71 (2)	2.679 (2)	179 (2)
O3—H3O⋯N1ⁱⁱ	0.87 (2)	1.86 (2)	2.728 (2)	171 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y+1, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810018842/pv2281sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018842/pv2281Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination complexes have absorbed considerable attention due to their diverse structures with 4,4'-bipyridine linker (Han et al., 2009). Moreover, hydrogen bond can also play a role in forming motif structures (Tomura & Yamashita, 2001). We have designed the title complex in an attempt to prepare crystaline magnetic materials and report its crystal structure in this paper.

The structure of the title complex is shown in Fig. 1, which reveals that it contains 2-(4-hydroxyphenyl)acetic acid and 4,4'-bipyridine in a ratio of 1:1. In the molecule of 2-(4-hydroxyphenyl)acetic acid, the acetyl torsion angle C(1)—C(7)—C(8)—O(2) is -32.1 (3) °, and in the molecule of 4,4'-bipyridine, the dihedral angle between the two pyridine rings is 23.41 (10) °. The two molecules arranged in the crystal at regular intervals with two O—H···N hydrogen bonds. The end to end hydrogen-bonding interactions lead to the formation of a one-dimensional triple-helix structure framework along the b-axis, Fig 2. Between adjacent triple-helix chains there exist weak π—π interactions.

Related literature top

For related functional complexes, see: Han et al. (2009). For hydrogen-bond motif structures, see: Tomura & Yamashita (2001).

Experimental top

2-(4-hydroxyphenyl)acetic acid (0.152 g, 1 mmol) and 4,4'-bipyridine (0.156 g, 1 mmol) were added to a mixed solution of ethanol (20 ml) and water (10 ml) with Cu(SO₄)₂ (0.127 g, 0.5 mmol) under stirred conditions at room temperature. A few minutes later a lot of blue deposit appeared. After the deposit was filtered out, a light blue solution was kept for evaporating. Colorless single crystals of the title complex were obtained about 19 days later.

Structure description top

For related functional complexes, see: Han et al. (2009). For hydrogen-bond motif structures, see: Tomura & Yamashita (2001).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The packing plot of the complex showing triple-helix chains.

2-(4-Hydroxyphenyl)acetic acid–4,4'-bipyridine (1/1) top

Crystal data top

C₁₀H₈N₂·C₈H₈O₃	F(000) = 1296
M_r = 308.33	D_x = 1.311 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3274 reflections
a = 25.3578 (6) Å	θ = 1.9–27.7°
b = 10.2305 (2) Å	µ = 0.09 mm⁻¹
c = 14.2546 (4) Å	T = 296 K
β = 122.321 (2)°	Block, colourless
V = 3125.03 (15) Å³	0.25 × 0.14 × 0.06 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	3650 independent reflections
Radiation source: fine-focus sealed tube	2128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ & ω scans	θ_max = 27.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→32
T_min = 0.984, T_max = 0.994	k = −13→13
24334 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.065P)² + 0.2994P] where P = (F_o² + 2F_c²)/3
3650 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₀H₈N₂·C₈H₈O₃	V = 3125.03 (15) Å³
M_r = 308.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.3578 (6) Å	µ = 0.09 mm⁻¹
b = 10.2305 (2) Å	T = 296 K
c = 14.2546 (4) Å	0.25 × 0.14 × 0.06 mm
β = 122.321 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3650 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2128 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.994	R_int = 0.043
24334 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.15 e Å⁻³
3650 reflections	Δρ_min = −0.16 e Å⁻³
214 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 > 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
C1	0.54789 (7)	0.32235 (16)	0.04851 (15)	0.0637 (5)
C2	0.54036 (7)	0.28856 (15)	0.13430 (17)	0.0674 (5)
H2A	0.5211	0.2098	0.1308	0.081*
C3	0.56064 (8)	0.36856 (15)	0.22505 (16)	0.0624 (5)
H3A	0.5554	0.3431	0.2822	0.075*
C4	0.58890 (7)	0.48680 (14)	0.23132 (14)	0.0540 (4)
C5	0.59659 (7)	0.52233 (14)	0.14611 (14)	0.0555 (4)
H5A	0.6156	0.6014	0.1494	0.067*
C6	0.57611 (8)	0.44072 (16)	0.05596 (15)	0.0618 (4)
H6A	0.5814	0.4660	−0.0011	0.074*
C7	0.52498 (9)	0.23409 (19)	−0.05088 (17)	0.0888 (7)
H7A	0.4826	0.2074	−0.0765	0.107*
H7B	0.5235	0.2843	−0.1100	0.107*
C8	0.56331 (9)	0.11343 (17)	−0.03167 (16)	0.0686 (5)
C9	0.27818 (7)	0.03470 (14)	0.13722 (13)	0.0531 (4)
C10	0.24522 (9)	−0.08224 (16)	0.10478 (15)	0.0668 (5)
H10A	0.2019	−0.0821	0.0680	0.080*
C11	0.27717 (11)	−0.19771 (17)	0.12756 (17)	0.0777 (6)
H11A	0.2543	−0.2749	0.1067	0.093*
C12	0.37044 (10)	−0.09378 (19)	0.20793 (17)	0.0780 (6)
H12A	0.4136	−0.0968	0.2423	0.094*
C13	0.34242 (8)	0.02609 (17)	0.19086 (15)	0.0669 (5)
H13A	0.3666	0.1015	0.2153	0.080*
C14	0.24634 (7)	0.16282 (14)	0.11616 (13)	0.0510 (4)
C15	0.18450 (8)	0.17940 (15)	0.03144 (14)	0.0600 (4)
H15A	0.1621	0.1097	−0.0147	0.072*
C16	0.15638 (8)	0.29964 (16)	0.01587 (15)	0.0656 (5)
H16A	0.1144	0.3078	−0.0394	0.079*
C17	0.24598 (9)	0.38940 (16)	0.15596 (15)	0.0657 (5)
H17A	0.2678	0.4619	0.1983	0.079*
C18	0.27730 (8)	0.27190 (15)	0.17954 (14)	0.0616 (4)
H18A	0.3188	0.2660	0.2375	0.074*
N1	0.33881 (9)	−0.20646 (15)	0.17762 (14)	0.0809 (5)
N2	0.18645 (7)	0.40479 (13)	0.07623 (12)	0.0636 (4)
O1	0.54120 (7)	0.01483 (14)	−0.08188 (14)	0.1052 (6)
O2	0.62304 (6)	0.12757 (12)	0.04163 (12)	0.0847 (5)
H2O	0.6456 (10)	0.046 (2)	0.0532 (17)	0.102*
O3	0.60808 (6)	0.56199 (12)	0.32305 (11)	0.0733 (4)
H3O	0.6234 (10)	0.635 (2)	0.3150 (17)	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0446 (9)	0.0533 (9)	0.0674 (12)	0.0112 (7)	0.0128 (8)	−0.0090 (8)
C2	0.0489 (10)	0.0440 (9)	0.0873 (13)	−0.0055 (7)	0.0218 (9)	−0.0050 (9)
C3	0.0525 (10)	0.0557 (9)	0.0743 (12)	−0.0072 (7)	0.0308 (9)	0.0034 (8)
C4	0.0497 (9)	0.0439 (8)	0.0632 (11)	−0.0009 (6)	0.0266 (8)	−0.0024 (7)
C5	0.0510 (9)	0.0436 (8)	0.0665 (11)	−0.0021 (6)	0.0279 (8)	0.0006 (7)
C6	0.0531 (10)	0.0616 (10)	0.0626 (11)	0.0104 (7)	0.0255 (9)	0.0015 (8)
C7	0.0684 (13)	0.0733 (12)	0.0792 (13)	0.0164 (10)	0.0090 (10)	−0.0249 (10)
C8	0.0630 (12)	0.0584 (10)	0.0692 (12)	0.0031 (8)	0.0252 (10)	−0.0127 (9)
C9	0.0596 (10)	0.0485 (8)	0.0501 (9)	0.0060 (7)	0.0286 (8)	0.0056 (7)
C10	0.0709 (12)	0.0541 (10)	0.0711 (12)	0.0042 (8)	0.0350 (10)	0.0022 (8)
C11	0.0991 (16)	0.0501 (10)	0.0807 (13)	0.0072 (10)	0.0461 (12)	0.0066 (9)
C12	0.0722 (13)	0.0720 (13)	0.0792 (13)	0.0231 (10)	0.0333 (11)	0.0192 (10)
C13	0.0621 (11)	0.0595 (10)	0.0687 (12)	0.0107 (8)	0.0280 (10)	0.0110 (8)
C14	0.0547 (9)	0.0484 (8)	0.0533 (9)	0.0038 (7)	0.0311 (8)	0.0066 (7)
C15	0.0599 (10)	0.0501 (9)	0.0636 (11)	0.0012 (7)	0.0288 (9)	−0.0005 (8)
C16	0.0555 (10)	0.0618 (10)	0.0669 (11)	0.0091 (8)	0.0243 (9)	0.0035 (9)
C17	0.0690 (12)	0.0540 (9)	0.0680 (11)	0.0023 (8)	0.0325 (10)	−0.0062 (8)
C18	0.0562 (10)	0.0567 (9)	0.0624 (11)	0.0022 (7)	0.0253 (9)	−0.0027 (8)
N1	0.1009 (14)	0.0620 (10)	0.0767 (11)	0.0285 (9)	0.0454 (10)	0.0179 (8)
N2	0.0656 (10)	0.0546 (8)	0.0665 (9)	0.0094 (7)	0.0327 (8)	−0.0004 (7)
O1	0.0818 (10)	0.0680 (9)	0.1354 (14)	−0.0077 (7)	0.0376 (9)	−0.0416 (9)
O2	0.0640 (9)	0.0596 (7)	0.0937 (10)	0.0124 (6)	0.0175 (8)	−0.0179 (7)
O3	0.0921 (10)	0.0576 (7)	0.0738 (8)	−0.0186 (6)	0.0467 (8)	−0.0124 (6)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C10—C11	1.370 (2)
C1—C6	1.382 (2)	C10—H10A	0.9300
C1—C7	1.510 (2)	C11—N1	1.330 (2)
C2—C3	1.377 (2)	C11—H11A	0.9300
C2—H2A	0.9300	C12—N1	1.337 (3)
C3—C4	1.384 (2)	C12—C13	1.372 (2)
C3—H3A	0.9300	C12—H12A	0.9300
C4—O3	1.3631 (19)	C13—H13A	0.9300
C4—C5	1.378 (2)	C14—C18	1.385 (2)
C5—C6	1.380 (2)	C14—C15	1.386 (2)
C5—H5A	0.9300	C15—C16	1.379 (2)
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.503 (2)	C16—N2	1.333 (2)
C7—H7A	0.9700	C16—H16A	0.9300
C7—H7B	0.9700	C17—N2	1.327 (2)
C8—O1	1.190 (2)	C17—C18	1.380 (2)
C8—O2	1.309 (2)	C17—H17A	0.9300
C9—C13	1.384 (2)	C18—H18A	0.9300
C9—C10	1.389 (2)	O2—H2O	0.97 (2)
C9—C14	1.484 (2)	O3—H3O	0.87 (2)

C2—C1—C6	117.60 (16)	C11—C10—H10A	120.3
C2—C1—C7	121.07 (18)	C9—C10—H10A	120.3
C6—C1—C7	121.33 (19)	N1—C11—C10	124.19 (18)
C3—C2—C1	121.66 (16)	N1—C11—H11A	117.9
C3—C2—H2A	119.2	C10—C11—H11A	117.9
C1—C2—H2A	119.2	N1—C12—C13	123.29 (19)
C2—C3—C4	120.03 (17)	N1—C12—H12A	118.4
C2—C3—H3A	120.0	C13—C12—H12A	118.4
C4—C3—H3A	120.0	C12—C13—C9	119.99 (17)
O3—C4—C5	123.41 (14)	C12—C13—H13A	120.0
O3—C4—C3	117.52 (16)	C9—C13—H13A	120.0
C5—C4—C3	119.07 (15)	C18—C14—C15	116.89 (14)
C4—C5—C6	120.07 (14)	C18—C14—C9	121.49 (14)
C4—C5—H5A	120.0	C15—C14—C9	121.61 (14)
C6—C5—H5A	120.0	C16—C15—C14	119.74 (16)
C5—C6—C1	121.56 (17)	C16—C15—H15A	120.1
C5—C6—H6A	119.2	C14—C15—H15A	120.1
C1—C6—H6A	119.2	N2—C16—C15	123.21 (16)
C8—C7—C1	115.68 (15)	N2—C16—H16A	118.4
C8—C7—H7A	108.4	C15—C16—H16A	118.4
C1—C7—H7A	108.4	N2—C17—C18	123.72 (16)
C8—C7—H7B	108.4	N2—C17—H17A	118.1
C1—C7—H7B	108.4	C18—C17—H17A	118.1
H7A—C7—H7B	107.4	C17—C18—C14	119.42 (16)
O1—C8—O2	123.08 (17)	C17—C18—H18A	120.3
O1—C8—C7	122.41 (17)	C14—C18—H18A	120.3
O2—C8—C7	114.47 (15)	C11—N1—C12	116.44 (15)
C13—C9—C10	116.75 (15)	C17—N2—C16	116.96 (14)
C13—C9—C14	121.38 (14)	C8—O2—H2O	111.5 (12)
C10—C9—C14	121.87 (15)	C4—O3—H3O	108.1 (14)
C11—C10—C9	119.30 (18)

C6—C1—C2—C3	−0.7 (2)	N1—C12—C13—C9	−1.8 (3)
C7—C1—C2—C3	−179.55 (15)	C10—C9—C13—C12	1.1 (3)
C1—C2—C3—C4	0.6 (2)	C14—C9—C13—C12	−179.22 (16)
C2—C3—C4—O3	−179.97 (15)	C13—C9—C14—C18	−23.0 (2)
C2—C3—C4—C5	−0.3 (2)	C10—C9—C14—C18	156.71 (16)
O3—C4—C5—C6	179.78 (14)	C13—C9—C14—C15	156.28 (16)
C3—C4—C5—C6	0.2 (2)	C10—C9—C14—C15	−24.1 (2)
C4—C5—C6—C1	−0.2 (2)	C18—C14—C15—C16	−1.8 (2)
C2—C1—C6—C5	0.5 (2)	C9—C14—C15—C16	178.93 (15)
C7—C1—C6—C5	179.37 (15)	C14—C15—C16—N2	2.6 (3)
C2—C1—C7—C8	−74.3 (2)	N2—C17—C18—C14	1.4 (3)
C6—C1—C7—C8	106.8 (2)	C15—C14—C18—C17	−0.1 (2)
C1—C7—C8—O1	150.2 (2)	C9—C14—C18—C17	179.18 (15)
C1—C7—C8—O2	−32.1 (3)	C10—C11—N1—C12	0.9 (3)
C13—C9—C10—C11	0.4 (3)	C13—C12—N1—C11	0.8 (3)
C14—C9—C10—C11	−179.26 (16)	C18—C17—N2—C16	−0.7 (3)
C9—C10—C11—N1	−1.5 (3)	C15—C16—N2—C17	−1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2ⁱ	0.97 (2)	1.71 (2)	2.679 (2)	179 (2)
O3—H3O···N1ⁱⁱ	0.87 (2)	1.86 (2)	2.728 (2)	171 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·C₈H₈O₃
M_r	308.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	25.3578 (6), 10.2305 (2), 14.2546 (4)
β (°)	122.321 (2)
V (Å³)	3125.03 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.14 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.984, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	24334, 3650, 2128
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.139, 1.06
No. of reflections	3650
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), 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—H2O···N2ⁱ	0.97 (2)	1.71 (2)	2.679 (2)	179 (2)
O3—H3O···N1ⁱⁱ	0.87 (2)	1.86 (2)	2.728 (2)	171 (2)

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

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, L., Zhou, Y., Wang, X. T., Li, X. & Tong, M. L. (2009). J. Mol. Struct. 923, 24–27. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tomura, M. & Yamashita, Y. (2001). Chem. Lett. 30, 532–533. Web of Science CSD CrossRef Google Scholar

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