Redetermined structure of 4,4'-bi-pyridine-1,4-phenyl-enedi-acetic acid (1/1) co-crystal.

The asymmetric unit of the title 1:1 co-crystal, C10H8N2·C10H10O4, consists of one half-mol-ecule each of 4,4'-bi-pyridine and 1,4-phenyl-enedi-acetic acid: the complete mol-ecules are generated by crystallographic inversion centres. The dihedral angle between the -CO2H group and the benzene ring in the diacid is 73.02 (7)°. In the crystal, the components are linked by O-H⋯N hydrogen bonds, generating [1-2-1] chains of alternating amine and carb-oxy-lic acid mol-ecules. The chains are cross-linked by C-H⋯O inter-actions. This structure was previously incorrectly described as a (C10H10N2)(2+)·(C10H8O4)(2-) mol-ecular salt [Jia et al. (2009 ▸). Acta Cryst. E65, o2490-o2490].

Related literature

For the previous erroneous report of this structure as a mol­ecular salt, see: Jia et al. (2009 ▸). For hydrogen-bonded co-crystals, see: Stahly (2009 ▸); Kavuru et al. (2010 ▸). For pharmaceutical co-crystals, see: Childs et al. (2009 ▸); Walsh et al. (2003 ▸). For a similar structure, see: Chinnakali et al. (1999 ▸).

Experimental

Crystal data

C10H8N2·C10H10O4

M = 350.36

Triclinic,

a = 4.5577 (5) Å

b = 6.9806 (8) Å

c = 13.7995 (15) Å

α = 99.508 (6)°

β = 94.297 (6)°

γ = 97.643 (7)°

V = 427.05 (8) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.20 × 0.17 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

8581 measured reflections

2405 independent reflections

1876 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.05

2405 reflections

155 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015017569/hb7506sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017569/hb7506Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017569/hb7506Isup3.doc

Click here for additional data file.

I . DOI: 10.1107/S2056989015017569/hb7506fig1.tif

The mol­ecular structure of (I) showing 50% probability displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S2056989015017569/hb7506fig2.tif

A view of the O—H⋯N, C—H⋯O and C—H⋯π inter­actions observed in the crystal structure of the title compound.

CCDC reference: 1423417

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H8N2·C10H10O4	V = 427.05 (8) Å3
Mr = 350.36	Z = 1
Triclinic, P1	F(000) = 184
a = 4.5577 (5) Å	Dx = 1.362 Mg m−3
b = 6.9806 (8) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.7995 (15) Å	µ = 0.10 mm−1
α = 99.508 (6)°	T = 296 K
β = 94.297 (6)°	Rectangular block, colourless
γ = 97.643 (7)°	0.20 × 0.17 × 0.13 mm

Bruker SMART CCD diffractometer	1876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 29.8°, θmin = 3.0°
phi and ω scans	h = −6→6
8581 measured reflections	k = −9→9
2405 independent reflections	l = −19→19

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)] = 0.041	All H-atom parameters refined
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0515P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2405 reflections	Δρmax = 0.19 e Å−3
155 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (11)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.8197 (2)	0.45294 (13)	−0.18830 (6)	0.0541 (3)
C1	0.7209 (2)	0.60720 (15)	−0.21279 (8)	0.0408 (3)
C2	0.5619 (3)	0.71533 (19)	−0.13310 (10)	0.0490 (3)
C3	0.7850 (2)	0.86342 (15)	−0.06291 (8)	0.0400 (3)
C4	0.9459 (3)	0.80852 (16)	0.01476 (9)	0.0454 (3)
C5	0.8422 (3)	1.05717 (17)	−0.07687 (8)	0.0446 (3)
O2	0.7616 (3)	0.66207 (15)	−0.28973 (7)	0.0675 (3)
N1	0.8832 (2)	0.73182 (15)	0.32203 (7)	0.0476 (3)
C6	0.8316 (3)	0.67172 (18)	0.40629 (9)	0.0517 (3)
C7	0.6844 (3)	0.77149 (18)	0.47798 (9)	0.0487 (3)
C8	0.5796 (2)	0.94340 (15)	0.46266 (7)	0.0376 (2)
C10	0.7840 (3)	0.8964 (2)	0.30711 (10)	0.0566 (3)
C9	0.6326 (3)	1.00451 (19)	0.37423 (9)	0.0532 (3)
H9	0.927 (5)	0.382 (3)	−0.2421 (15)	0.104 (7)*
H3	0.908 (3)	0.676 (2)	0.0263 (11)	0.061 (4)*
H4	0.731 (3)	1.100 (2)	−0.1302 (11)	0.055 (4)*
H6	0.660 (3)	0.722 (2)	0.5378 (12)	0.067 (4)*
H1	0.462 (4)	0.621 (2)	−0.0977 (12)	0.065 (4)*
H8	0.822 (4)	0.935 (2)	0.2459 (13)	0.073 (5)*
H7	0.560 (4)	1.122 (3)	0.3533 (13)	0.081 (5)*
H2	0.412 (4)	0.787 (3)	−0.1669 (12)	0.071 (5)*
H5	0.902 (4)	0.551 (3)	0.4159 (12)	0.071 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0764 (6)	0.0483 (5)	0.0463 (5)	0.0272 (4)	0.0173 (4)	0.0141 (4)
C1	0.0449 (6)	0.0370 (5)	0.0403 (5)	0.0071 (4)	0.0035 (4)	0.0055 (4)
C2	0.0434 (6)	0.0489 (6)	0.0549 (7)	0.0115 (5)	0.0119 (5)	0.0025 (5)
C3	0.0431 (5)	0.0405 (5)	0.0396 (5)	0.0148 (4)	0.0163 (4)	0.0046 (4)
C4	0.0580 (7)	0.0363 (5)	0.0467 (6)	0.0141 (5)	0.0146 (5)	0.0116 (4)
C5	0.0545 (7)	0.0452 (6)	0.0394 (5)	0.0184 (5)	0.0097 (5)	0.0116 (4)
O2	0.1023 (8)	0.0630 (6)	0.0502 (5)	0.0351 (6)	0.0215 (5)	0.0232 (4)
N1	0.0507 (6)	0.0478 (5)	0.0450 (5)	0.0158 (4)	0.0075 (4)	0.0023 (4)
C6	0.0643 (8)	0.0439 (6)	0.0511 (7)	0.0221 (6)	0.0096 (6)	0.0075 (5)
C7	0.0631 (7)	0.0441 (6)	0.0443 (6)	0.0189 (5)	0.0116 (5)	0.0117 (5)
C8	0.0370 (5)	0.0374 (5)	0.0379 (5)	0.0073 (4)	0.0026 (4)	0.0045 (4)
C10	0.0714 (9)	0.0614 (8)	0.0466 (7)	0.0285 (6)	0.0200 (6)	0.0159 (6)
C9	0.0691 (8)	0.0515 (7)	0.0490 (6)	0.0284 (6)	0.0181 (6)	0.0166 (5)

O1—C1	1.3051 (13)	C5—H4	0.972 (14)
O1—H9	1.02 (2)	N1—C6	1.3264 (16)
C1—O2	1.2056 (14)	N1—C10	1.3301 (16)
C1—C2	1.5147 (16)	C6—C7	1.3820 (17)
C2—C3	1.5108 (17)	C6—H5	0.964 (17)
C2—H1	0.970 (16)	C7—C8	1.3906 (15)
C2—H2	1.027 (17)	C7—H6	0.955 (16)
C3—C4	1.3877 (16)	C8—C9	1.3850 (16)
C3—C5	1.3908 (15)	C8—C8ii	1.486 (2)
C4—C5i	1.3844 (18)	C10—C9	1.3810 (17)
C4—H3	0.961 (15)	C10—H8	0.950 (18)
C5—C4i	1.3844 (18)	C9—H7	0.998 (19)
C1—O1—H9	112.6 (12)	C3—C5—H4	120.1 (8)
O2—C1—O1	123.26 (10)	C6—N1—C10	117.10 (10)
O2—C1—C2	123.39 (11)	N1—C6—C7	123.47 (11)
O1—C1—C2	113.30 (10)	N1—C6—H5	116.3 (10)
C3—C2—C1	109.58 (9)	C7—C6—H5	120.2 (10)
C3—C2—H1	110.0 (9)	C6—C7—C8	119.66 (11)
C1—C2—H1	108.9 (10)	C6—C7—H6	119.0 (10)
C3—C2—H2	109.4 (9)	C8—C7—H6	121.4 (10)
C1—C2—H2	107.7 (9)	C9—C8—C7	116.53 (10)
H1—C2—H2	111.2 (13)	C9—C8—C8ii	121.59 (12)
C4—C3—C5	118.28 (11)	C7—C8—C8ii	121.88 (12)
C4—C3—C2	121.06 (10)	N1—C10—C9	123.35 (12)
C5—C3—C2	120.61 (10)	N1—C10—H8	115.3 (10)
C5i—C4—C3	120.99 (10)	C9—C10—H8	121.3 (10)
C5i—C4—H3	119.3 (9)	C10—C9—C8	119.89 (11)
C3—C4—H3	119.7 (9)	C10—C9—H7	116.0 (11)
C4i—C5—C3	120.73 (11)	C8—C9—H7	124.1 (11)
C4i—C5—H4	119.2 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H9···N1iii	1.02 (2)	1.62 (2)	2.6373 (13)	176 (2)
C7—H6···O2iv	0.954 (16)	2.504 (16)	3.4196 (16)	160.8 (11)
C9—H7···O2v	1.00 (2)	2.45 (2)	3.4205 (18)	162.2 (16)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H9N1i	1.02(2)	1.62(2)	2.6373(13)	176(2)
C7H6O2ii	0.954(16)	2.504(16)	3.4196(16)	160.8(11)
C9H7O2iii	1.00(2)	2.45(2)	3.4205(18)	162.2(16)

Symmetry codes: (i) ; (ii) ; (iii) .