4,4'-Bipyridine-3-(thio-phen-3-yl)acrylic acid (1/2).

In the title 1/2 adduct, C(10)H(8)N(2)·2C(7)H(6)O(2)S, the dihedral angle between the pyridine rings is 18.41 (11)°. In the thio-phene-acrylic acid mol-ecules, the dihedral angles between the respective thio-phene and acrylic acid units are 5.52 (17)° and 23.92 (9)°. In the crystal, the components are linked via O-H⋯N hydrogen-bonding inter-actions, forming units of two 3-thio-phene-acrylic acid mol-ecules and one 4,4'-bipyridine mol-ecule.

Related literature

For the synthesis and in vitro anti­bacterial activity of oxazolidines, see: Srivastava et al. (2008 ▶). For crystal engineering co-crystal and polymorph architectures, see: Friščić & MacGillivray (2009 ▶); Eccles et al. (2010 ▶). For the supra­molecular construction of mol­ecular ladders, see: Gao et al. (2004 ▶); MacGillivray et al. (2008 ▶); Friščić & MacGillivray (2005 ▶). For C—H⋯O hydrogen bonds in supra­molecular design, see: Desiraju (1996 ▶) and for C—H⋯π inter­actions in crystal engineering, see: Desiraju (2002 ▶).

Experimental

Crystal data

C10H8N2·2C7H6O2S

M = 464.54

Triclinic,

a = 7.3454 (5) Å

b = 10.7319 (8) Å

c = 15.0196 (11) Å

α = 102.518 (6)°

β = 103.648 (6)°

γ = 94.892 (6)°

V = 1111.54 (14) Å3

Z = 2

Cu Kα radiation

μ = 2.46 mm−1

T = 293 K

0.37 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.692, T max = 1.000

9038 measured reflections

4344 independent reflections

3498 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.05

4344 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction 2009) ▶; cell refinement: CrysAlis RED (Oxford Diffraction, 2009) ▶; data reduction: CrysAlis RED ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035823/si2368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035823/si2368Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035823/si2368Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H8N2·2C7H6O2S	Z = 2
Mr = 464.54	F(000) = 484
Triclinic, P1	Dx = 1.388 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.3454 (5) Å	Cell parameters from 3251 reflections
b = 10.7319 (8) Å	θ = 3.1–72.9°
c = 15.0196 (11) Å	µ = 2.46 mm−1
α = 102.518 (6)°	T = 293 K
β = 103.648 (6)°	Plate, white
γ = 94.892 (6)°	0.37 × 0.15 × 0.10 mm
V = 1111.54 (14) Å3

Xcalibur, Sapphire3 diffractometer	4344 independent reflections
Radiation source: fine-focus sealed tube	3498 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 15.9853 pixels mm-1	θmax = 72.1°, θmin = 3.1°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→12
Tmin = 0.692, Tmax = 1.000	l = −18→13
9038 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.2003P] where P = (Fo2 + 2Fc2)/3
4344 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0548 (3)	0.0002 (2)	−0.17354 (15)	0.0547 (5)
H1	0.0689	−0.0528	−0.1316	0.066*
C2	0.1988 (3)	0.08388 (19)	−0.17968 (13)	0.0439 (4)
C3	0.1338 (3)	0.1521 (2)	−0.25031 (15)	0.0542 (5)
H3	0.2120	0.2136	−0.2645	0.065*
C4	−0.0525 (3)	0.1183 (2)	−0.29432 (16)	0.0611 (6)
H4	−0.1172	0.1531	−0.3420	0.073*
C5	0.3899 (3)	0.09887 (19)	−0.12014 (13)	0.0447 (4)
H5	0.4097	0.0504	−0.0753	0.054*
C6	0.5392 (3)	0.1746 (2)	−0.12320 (14)	0.0479 (4)
H6	0.5262	0.2230	−0.1681	0.058*
C7	0.7262 (3)	0.18356 (19)	−0.05652 (14)	0.0467 (4)
C8	0.2956 (3)	0.2219 (2)	0.08555 (15)	0.0559 (5)
H8	0.2325	0.1394	0.0762	0.067*
C9	0.4852 (3)	0.2485 (2)	0.13424 (15)	0.0508 (5)
H9	0.5459	0.1850	0.1574	0.061*
C10	0.5840 (3)	0.36980 (18)	0.14838 (13)	0.0429 (4)
C11	0.4821 (3)	0.4604 (2)	0.11311 (16)	0.0571 (5)
H11	0.5412	0.5437	0.1213	0.069*
C12	0.2929 (3)	0.4253 (2)	0.06605 (17)	0.0610 (6)
H12	0.2273	0.4872	0.0432	0.073*
C13	0.7889 (3)	0.40367 (18)	0.19703 (13)	0.0430 (4)
C14	0.8822 (3)	0.3308 (2)	0.25474 (15)	0.0537 (5)
H14	0.8163	0.2593	0.2646	0.064*
C15	1.0737 (3)	0.3656 (2)	0.29725 (16)	0.0575 (5)
H15	1.1340	0.3149	0.3347	0.069*
C16	1.0874 (3)	0.5381 (2)	0.23340 (17)	0.0595 (6)
H16	1.1565	0.6104	0.2263	0.071*
C17	0.8972 (3)	0.5096 (2)	0.18718 (16)	0.0556 (5)
H17	0.8417	0.5614	0.1494	0.067*
C18	1.2549 (3)	0.6734 (2)	0.52895 (16)	0.0584 (5)
H18	1.2472	0.5856	0.5026	0.070*
C19	1.1052 (3)	0.7401 (2)	0.51574 (13)	0.0475 (4)
C20	1.1585 (3)	0.8722 (2)	0.56515 (17)	0.0614 (6)
H20	1.0746	0.9324	0.5652	0.074*
C21	1.3461 (3)	0.9011 (2)	0.61250 (18)	0.0660 (6)
H21	1.4053	0.9830	0.6477	0.079*
C22	0.9150 (3)	0.6807 (2)	0.46025 (13)	0.0490 (5)
H22	0.8956	0.5918	0.4362	0.059*
C23	0.7683 (3)	0.7418 (2)	0.44109 (15)	0.0548 (5)
H23	0.7857	0.8303	0.4668	0.066*
C24	0.5778 (3)	0.6803 (2)	0.38173 (15)	0.0549 (5)
O1	0.7640 (2)	0.11251 (16)	−0.00462 (11)	0.0637 (4)
O2	0.8489 (2)	0.27837 (16)	−0.05983 (12)	0.0645 (4)
H2	0.9510	0.2794	−0.0227	0.097*
O3	0.4670 (2)	0.74129 (19)	0.34314 (14)	0.0809 (6)
O4	0.5423 (2)	0.55602 (16)	0.37539 (13)	0.0650 (4)
H4A	0.4325	0.5289	0.3450	0.098*
S1	−0.15372 (8)	0.00362 (7)	−0.25123 (4)	0.0671 (2)
S2	1.45740 (8)	0.76787 (7)	0.59882 (5)	0.0697 (2)
N1	0.1992 (2)	0.30804 (19)	0.05151 (13)	0.0568 (5)
N2	1.1767 (2)	0.46765 (18)	0.28753 (13)	0.0552 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0390 (10)	0.0657 (13)	0.0557 (12)	0.0000 (9)	0.0023 (8)	0.0207 (10)
C2	0.0382 (10)	0.0472 (10)	0.0429 (9)	0.0050 (8)	0.0058 (7)	0.0098 (8)
C3	0.0474 (11)	0.0583 (12)	0.0553 (12)	0.0055 (9)	0.0045 (9)	0.0213 (10)
C4	0.0512 (12)	0.0715 (14)	0.0548 (12)	0.0142 (11)	−0.0025 (9)	0.0193 (11)
C5	0.0378 (10)	0.0497 (10)	0.0448 (10)	0.0062 (8)	0.0048 (8)	0.0147 (8)
C6	0.0390 (10)	0.0518 (11)	0.0511 (11)	0.0052 (8)	0.0018 (8)	0.0200 (9)
C7	0.0358 (9)	0.0512 (11)	0.0511 (10)	0.0048 (8)	0.0049 (8)	0.0163 (9)
C8	0.0430 (11)	0.0567 (12)	0.0597 (12)	−0.0069 (9)	0.0073 (9)	0.0086 (10)
C9	0.0421 (10)	0.0491 (11)	0.0569 (11)	0.0014 (8)	0.0065 (9)	0.0130 (9)
C10	0.0351 (9)	0.0489 (10)	0.0400 (9)	0.0028 (8)	0.0049 (7)	0.0074 (8)
C11	0.0437 (11)	0.0502 (11)	0.0701 (13)	0.0020 (9)	−0.0004 (10)	0.0178 (10)
C12	0.0426 (11)	0.0653 (14)	0.0701 (14)	0.0101 (10)	0.0000 (10)	0.0208 (11)
C13	0.0338 (9)	0.0472 (10)	0.0422 (9)	0.0030 (7)	0.0039 (7)	0.0065 (8)
C14	0.0396 (10)	0.0610 (12)	0.0590 (12)	0.0026 (9)	0.0047 (9)	0.0224 (10)
C15	0.0415 (11)	0.0663 (14)	0.0609 (13)	0.0078 (10)	0.0005 (9)	0.0220 (11)
C16	0.0406 (11)	0.0591 (13)	0.0695 (14)	−0.0079 (9)	0.0010 (10)	0.0165 (11)
C17	0.0422 (11)	0.0544 (12)	0.0629 (13)	−0.0014 (9)	−0.0013 (9)	0.0186 (10)
C18	0.0406 (11)	0.0641 (13)	0.0612 (13)	0.0030 (9)	0.0058 (9)	0.0059 (10)
C19	0.0372 (10)	0.0588 (12)	0.0421 (9)	0.0004 (8)	0.0040 (7)	0.0121 (9)
C20	0.0439 (12)	0.0593 (13)	0.0700 (14)	0.0058 (10)	−0.0008 (10)	0.0101 (11)
C21	0.0461 (12)	0.0624 (14)	0.0716 (15)	−0.0046 (10)	−0.0014 (10)	0.0021 (11)
C22	0.0390 (10)	0.0576 (12)	0.0453 (10)	−0.0037 (9)	0.0036 (8)	0.0140 (9)
C23	0.0406 (11)	0.0612 (13)	0.0559 (12)	−0.0025 (9)	0.0000 (9)	0.0182 (10)
C24	0.0371 (10)	0.0682 (14)	0.0571 (12)	−0.0024 (9)	0.0027 (9)	0.0248 (10)
O1	0.0460 (8)	0.0779 (11)	0.0686 (10)	0.0059 (7)	−0.0012 (7)	0.0399 (9)
O2	0.0389 (8)	0.0669 (10)	0.0806 (11)	−0.0046 (7)	−0.0068 (7)	0.0324 (8)
O3	0.0477 (9)	0.0871 (12)	0.0997 (13)	−0.0059 (9)	−0.0160 (9)	0.0502 (11)
O4	0.0359 (8)	0.0668 (10)	0.0792 (11)	−0.0008 (7)	−0.0064 (7)	0.0169 (8)
S1	0.0359 (3)	0.0853 (4)	0.0685 (4)	−0.0024 (3)	−0.0014 (2)	0.0156 (3)
S2	0.0343 (3)	0.0880 (5)	0.0729 (4)	0.0059 (3)	−0.0003 (2)	0.0073 (3)
N1	0.0350 (9)	0.0705 (12)	0.0563 (10)	−0.0002 (8)	0.0024 (7)	0.0110 (9)
N2	0.0359 (9)	0.0640 (11)	0.0558 (10)	0.0012 (8)	0.0006 (7)	0.0089 (8)

C1—C2	1.361 (3)	C13—C14	1.392 (3)
C1—S1	1.701 (2)	C14—C15	1.382 (3)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.430 (3)	C15—N2	1.332 (3)
C2—C5	1.451 (3)	C15—H15	0.9300
C3—C4	1.351 (3)	C16—N2	1.328 (3)
C3—H3	0.9300	C16—C17	1.380 (3)
C4—S1	1.703 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.324 (3)	C18—C19	1.362 (3)
C5—H5	0.9300	C18—S2	1.699 (2)
C6—C7	1.478 (3)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.423 (3)
C7—O1	1.207 (2)	C19—C22	1.456 (3)
C7—O2	1.318 (2)	C20—C21	1.367 (3)
C8—N1	1.328 (3)	C20—H20	0.9300
C8—C9	1.385 (3)	C21—S2	1.705 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.383 (3)	C22—C23	1.315 (3)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.395 (3)	C23—C24	1.479 (3)
C10—C13	1.485 (2)	C23—H23	0.9300
C11—C12	1.380 (3)	C24—O3	1.208 (3)
C11—H11	0.9300	C24—O4	1.315 (3)
C12—N1	1.330 (3)	O2—H2	0.8200
C12—H12	0.9300	O4—H4A	0.8200
C13—C17	1.386 (3)
C2—C1—S1	112.31 (16)	C15—C14—C13	119.4 (2)
C2—C1—H1	123.8	C15—C14—H14	120.3
S1—C1—H1	123.8	C13—C14—H14	120.3
C1—C2—C3	110.97 (18)	N2—C15—C14	123.6 (2)
C1—C2—C5	122.51 (18)	N2—C15—H15	118.2
C3—C2—C5	126.52 (18)	C14—C15—H15	118.2
C4—C3—C2	113.3 (2)	N2—C16—C17	123.3 (2)
C4—C3—H3	123.4	N2—C16—H16	118.3
C2—C3—H3	123.4	C17—C16—H16	118.3
C3—C4—S1	111.33 (17)	C16—C17—C13	120.1 (2)
C3—C4—H4	124.3	C16—C17—H17	120.0
S1—C4—H4	124.3	C13—C17—H17	120.0
C6—C5—C2	126.60 (18)	C19—C18—S2	112.62 (18)
C6—C5—H5	116.7	C19—C18—H18	123.7
C2—C5—H5	116.7	S2—C18—H18	123.7
C5—C6—C7	121.21 (18)	C18—C19—C20	111.27 (19)
C5—C6—H6	119.4	C18—C19—C22	123.4 (2)
C7—C6—H6	119.4	C20—C19—C22	125.35 (19)
O1—C7—O2	123.23 (18)	C21—C20—C19	112.8 (2)
O1—C7—C6	124.35 (18)	C21—C20—H20	123.6
O2—C7—C6	112.42 (17)	C19—C20—H20	123.6
N1—C8—C9	123.5 (2)	C20—C21—S2	111.29 (18)
N1—C8—H8	118.3	C20—C21—H21	124.4
C9—C8—H8	118.3	S2—C21—H21	124.4
C10—C9—C8	119.7 (2)	C23—C22—C19	125.7 (2)
C10—C9—H9	120.1	C23—C22—H22	117.1
C8—C9—H9	120.1	C19—C22—H22	117.1
C9—C10—C11	116.67 (18)	C22—C23—C24	124.9 (2)
C9—C10—C13	122.63 (18)	C22—C23—H23	117.6
C11—C10—C13	120.69 (18)	C24—C23—H23	117.6
C12—C11—C10	119.5 (2)	O3—C24—O4	124.2 (2)
C12—C11—H11	120.3	O3—C24—C23	121.6 (2)
C10—C11—H11	120.2	O4—C24—C23	114.25 (18)
N1—C12—C11	123.6 (2)	C7—O2—H2	109.5
N1—C12—H12	118.2	C24—O4—H4A	109.5
C11—C12—H12	118.2	C1—S1—C4	92.12 (11)
C17—C13—C14	116.54 (18)	C18—S2—C21	91.96 (11)
C17—C13—C10	121.64 (18)	C8—N1—C12	117.01 (18)
C14—C13—C10	121.82 (18)	C16—N2—C15	117.01 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1i	0.82	1.86	2.668 (2)	168.
O4—H4A···N2ii	0.82	1.87	2.684 (2)	174.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.82	1.86	2.668 (2)	168
O4—H4A⋯N2ii	0.82	1.87	2.684 (2)	174

Symmetry codes: (i) ; (ii) .