4,4'-Bipyridine-5-fluoro-isophthalic acid (1/1).

Co-crystallization of 5-fluoro-isophthalic acid (H(2)fip) with 4,4'-bipyridine (bipy) leads to the formation of the title compound [(H(2)fip)(bipy)], C(8)H(5)FO(4)·C(10)H(8)N(2), with an acid-base molar ratio of 1:1. The acid and base subunits are arrange alternately in the crystal structure, displaying a wave-like tape motif via inter-molecular O-H⋯N and C-H⋯O hydrogen bonds [carbox-yl-pyridine synthon of R(2) (2)(7) hydrogen-bond notation], which are further combined into a two-dimensional architecture through C-H⋯F inter-actions involving the bipy and H(2)fip mol-ecules.

Related literature

For the supra­molecular synthon approach in crystal engineering, see: Desiraju (1995 ▶); Nangia & Desiraju (1998 ▶). For background to co-crystallization, see: Aakeröy & Salmon (2005 ▶); Sharma & Zaworotko (1996 ▶); Schultheiss & n class="Chemical">Newman (2009 ▶). For co-crystals with a carbox­yl–pyridyl heterosynthon, see: Etter (1990 ▶); Shan et al. (2002 ▶); Du et al. (2005 ▶). For co-crystals of halogen-substituted dicarb­oxy­lic acids, see: He et al. (2009 ▶).

Experimental

Crystal data

C8H5FO4·C10H8N2

M = 340.30

Monoclinic,

a = 7.1711 (13) Å

b = 20.106 (4) Å

c = 11.272 (2) Å

β = 106.781 (2)°

V = 1556.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.34 × 0.32 × 0.32 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.963, T max = 0.967

11109 measured reflections

2742 independent reflections

1956 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.166

S = 1.09

2742 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004016/vm2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004016/vm2069Isup2.hkl

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

C8H5FO4·C10H8N2	F(000) = 704
Mr = 340.30	Dx = 1.453 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2260 reflections
a = 7.1711 (13) Å	θ = 2.1–21.8°
b = 20.106 (4) Å	µ = 0.11 mm−1
c = 11.272 (2) Å	T = 296 K
β = 106.781 (2)°	Block, colorless
V = 1556.0 (5) Å3	0.34 × 0.32 × 0.32 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2742 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.963, Tmax = 0.967	k = −23→22
11109 measured reflections	l = −13→13

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.067P)2 + 1.097P] where P = (Fo2 + 2Fc2)/3
2742 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.72 e Å−3
1 restraint	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2245 (5)	0.3051 (2)	−0.1085 (3)	0.0680 (10)
H1	0.2529	0.2771	−0.1667	0.082*
C2	0.2595 (5)	0.28299 (18)	0.0108 (3)	0.0578 (9)
H2	0.3103	0.2406	0.0319	0.069*
C3	0.2198 (4)	0.32356 (15)	0.1013 (3)	0.0463 (7)
C4	0.1530 (5)	0.38653 (18)	0.0671 (3)	0.0618 (9)
H4	0.1293	0.4163	0.1242	0.074*
C5	0.1208 (5)	0.40493 (18)	−0.0617 (4)	0.0681 (9)
H5	0.0760	0.4475	−0.0870	0.082*
C6	0.2374 (4)	0.29661 (14)	0.2275 (2)	0.0390 (6)
C7	0.2065 (4)	0.22960 (14)	0.2432 (3)	0.0472 (7)
H7	0.1809	0.2009	0.1758	0.057*
C8	0.2138 (5)	0.20553 (15)	0.3592 (3)	0.0484 (7)
H8	0.1927	0.1603	0.3672	0.058*
C9	0.2766 (5)	0.33605 (15)	0.3328 (3)	0.0512 (8)
H9	0.2999	0.3813	0.3279	0.061*
C10	0.2807 (5)	0.30759 (15)	0.4452 (3)	0.0522 (8)
H10	0.3070	0.3350	0.5146	0.063*
C11	0.1900 (4)	0.11407 (14)	0.6366 (3)	0.0420 (7)
C12	0.1879 (4)	0.07233 (13)	0.7462 (2)	0.0374 (6)
C13	0.2825 (4)	0.09158 (14)	0.8674 (2)	0.0401 (7)
H13	0.3453	0.1325	0.8829	0.048*
C14	0.2827 (4)	0.04932 (14)	0.9653 (2)	0.0431 (7)
C15	0.1878 (5)	−0.01089 (15)	0.9423 (3)	0.0498 (8)
H15	0.1868	−0.0393	1.0072	0.060*
C16	0.0951 (5)	−0.02820 (14)	0.8225 (3)	0.0482 (7)
C17	0.0933 (4)	0.01109 (14)	0.7225 (3)	0.0424 (7)
H17	0.0313	−0.0027	0.6420	0.051*
C18	0.3876 (5)	0.06363 (18)	1.0980 (3)	0.0558 (9)
F1	0.0045 (3)	−0.08851 (9)	0.80111 (18)	0.0751 (7)
N1	0.1528 (4)	0.36369 (18)	−0.1434 (3)	0.0707 (8)
N2	0.2493 (4)	0.24332 (12)	0.4599 (2)	0.0453 (6)
O1	0.2483 (3)	0.17584 (10)	0.66511 (18)	0.0521 (6)
H1A	0.2473	0.1961	0.6018	0.078*
O2	0.1424 (4)	0.09213 (11)	0.53240 (18)	0.0615 (7)
O3	0.4816 (4)	0.12082 (13)	1.11386 (19)	0.0662 (7)
H3	0.5535	0.1231	1.1850	0.099*
O4	0.3880 (4)	0.02582 (13)	1.1812 (2)	0.0745 (8)

	U11	U22	U33	U12	U13	U23
C1	0.065 (2)	0.091 (3)	0.046 (2)	−0.003 (2)	0.0142 (17)	0.0128 (19)
C2	0.061 (2)	0.075 (2)	0.0364 (17)	−0.0063 (17)	0.0124 (15)	0.0050 (16)
C3	0.0388 (15)	0.0540 (18)	0.0413 (17)	−0.0042 (13)	0.0037 (13)	0.0110 (14)
C4	0.062 (2)	0.060 (2)	0.061 (2)	0.0019 (16)	0.0123 (17)	0.0205 (17)
C5	0.068 (2)	0.052 (2)	0.078 (2)	0.0076 (17)	0.0099 (19)	0.0185 (15)
C6	0.0388 (15)	0.0420 (16)	0.0348 (15)	−0.0001 (12)	0.0081 (12)	0.0051 (12)
C7	0.0608 (19)	0.0430 (17)	0.0358 (16)	−0.0047 (14)	0.0110 (14)	−0.0032 (13)
C8	0.0643 (19)	0.0401 (17)	0.0395 (17)	−0.0050 (14)	0.0130 (14)	0.0029 (13)
C9	0.072 (2)	0.0363 (16)	0.0461 (18)	−0.0036 (15)	0.0182 (16)	0.0005 (13)
C10	0.074 (2)	0.0449 (18)	0.0371 (17)	−0.0070 (15)	0.0158 (15)	−0.0064 (13)
C11	0.0455 (16)	0.0424 (17)	0.0364 (16)	−0.0014 (13)	0.0090 (13)	−0.0012 (13)
C12	0.0407 (15)	0.0392 (15)	0.0317 (14)	0.0026 (12)	0.0095 (12)	0.0003 (11)
C13	0.0442 (16)	0.0368 (15)	0.0377 (15)	0.0009 (12)	0.0092 (12)	−0.0053 (12)
C14	0.0488 (16)	0.0508 (18)	0.0285 (14)	0.0109 (13)	0.0091 (12)	0.0004 (12)
C15	0.067 (2)	0.0463 (18)	0.0365 (16)	0.0066 (15)	0.0154 (15)	0.0074 (13)
C16	0.0629 (19)	0.0372 (16)	0.0444 (17)	−0.0057 (14)	0.0156 (15)	0.0032 (13)
C17	0.0491 (17)	0.0424 (16)	0.0325 (15)	−0.0023 (13)	0.0066 (13)	−0.0017 (12)
C18	0.059 (2)	0.067 (2)	0.0395 (18)	0.0141 (17)	0.0113 (15)	−0.0101 (17)
F1	0.1104 (17)	0.0482 (11)	0.0623 (12)	−0.0268 (11)	0.0179 (11)	0.0032 (9)
N1	0.0663 (19)	0.091 (2)	0.0517 (18)	−0.0038 (17)	0.0114 (14)	0.0132 (14)
N2	0.0574 (15)	0.0436 (14)	0.0347 (13)	−0.0042 (11)	0.0131 (11)	0.0021 (11)
O1	0.0731 (14)	0.0454 (12)	0.0361 (11)	−0.0108 (10)	0.0129 (10)	0.0004 (9)
O2	0.0936 (18)	0.0562 (14)	0.0324 (12)	−0.0184 (12)	0.0147 (11)	−0.0025 (10)
O3	0.0738 (16)	0.0816 (18)	0.0352 (12)	0.0014 (13)	0.0030 (11)	−0.0124 (11)
O4	0.101 (2)	0.0853 (18)	0.0302 (12)	0.0180 (15)	0.0084 (12)	0.0083 (12)

C1—N1	1.301 (5)	C10—H10	0.9300
C1—C2	1.368 (4)	C11—O2	1.208 (3)
C1—H1	0.9300	C11—O1	1.320 (3)
C2—C3	1.398 (4)	C11—C12	1.497 (4)
C2—H2	0.9300	C12—C13	1.393 (4)
C3—C4	1.369 (4)	C12—C17	1.394 (4)
C3—C6	1.493 (4)	C13—C14	1.392 (4)
C4—C5	1.451 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.376 (4)
C5—N1	1.308 (5)	C14—C18	1.496 (4)
C5—H5	0.9300	C15—C16	1.367 (4)
C6—C7	1.385 (4)	C15—H15	0.9300
C6—C9	1.387 (4)	C16—F1	1.364 (3)
C7—C8	1.381 (4)	C16—C17	1.373 (4)
C7—H7	0.9300	C17—H17	0.9300
C8—N2	1.328 (4)	C18—O4	1.207 (4)
C8—H8	0.9300	C18—O3	1.319 (4)
C9—C10	1.382 (4)	O1—H1A	0.8200
C9—H9	0.9300	O3—H3	0.8200
C10—N2	1.330 (4)
N1—C1—C2	122.4 (4)	C9—C10—H10	118.1
N1—C1—H1	118.8	O2—C11—O1	124.1 (3)
C2—C1—H1	118.8	O2—C11—C12	122.0 (3)
C1—C2—C3	120.6 (4)	O1—C11—C12	113.9 (2)
C1—C2—H2	119.7	C13—C12—C17	120.4 (2)
C3—C2—H2	119.7	C13—C12—C11	122.4 (2)
C4—C3—C2	117.6 (3)	C17—C12—C11	117.2 (2)
C4—C3—C6	122.0 (3)	C14—C13—C12	119.7 (3)
C2—C3—C6	120.3 (3)	C14—C13—H13	120.1
C3—C4—C5	117.3 (3)	C12—C13—H13	120.1
C3—C4—H4	121.3	C15—C14—C13	120.0 (3)
C5—C4—H4	121.3	C15—C14—C18	115.9 (3)
N1—C5—C4	122.3 (3)	C13—C14—C18	124.1 (3)
N1—C5—H5	118.9	C16—C15—C14	118.9 (3)
C4—C5—H5	118.9	C16—C15—H15	120.6
C7—C6—C9	116.6 (2)	C14—C15—H15	120.6
C7—C6—C3	120.1 (3)	F1—C16—C15	118.2 (3)
C9—C6—C3	123.3 (3)	F1—C16—C17	118.4 (3)
C8—C7—C6	119.9 (3)	C15—C16—C17	123.4 (3)
C8—C7—H7	120.1	C16—C17—C12	117.5 (3)
C6—C7—H7	120.1	C16—C17—H17	121.2
N2—C8—C7	123.7 (3)	C12—C17—H17	121.2
N2—C8—H8	118.2	O4—C18—O3	123.9 (3)
C7—C8—H8	118.2	O4—C18—C14	122.9 (3)
C10—C9—C6	119.5 (3)	O3—C18—C14	113.2 (3)
C10—C9—H9	120.2	C1—N1—C5	119.7 (3)
C6—C9—H9	120.2	C8—N2—C10	116.5 (2)
N2—C10—C9	123.8 (3)	C11—O1—H1A	109.5
N2—C10—H10	118.1	C18—O3—H3	109.5
N1—C1—C2—C3	−0.3 (5)	C17—C12—C13—C14	0.1 (4)
C1—C2—C3—C4	−2.7 (5)	C11—C12—C13—C14	−177.2 (2)
C1—C2—C3—C6	173.2 (3)	C12—C13—C14—C15	−0.7 (4)
C2—C3—C4—C5	2.7 (5)	C12—C13—C14—C18	176.9 (3)
C6—C3—C4—C5	−173.2 (3)	C13—C14—C15—C16	0.3 (4)
C3—C4—C5—N1	0.2 (5)	C18—C14—C15—C16	−177.6 (3)
C4—C3—C6—C7	146.8 (3)	C14—C15—C16—F1	178.9 (3)
C2—C3—C6—C7	−29.0 (4)	C14—C15—C16—C17	0.9 (5)
C4—C3—C6—C9	−30.5 (4)	F1—C16—C17—C12	−179.6 (3)
C2—C3—C6—C9	153.8 (3)	C15—C16—C17—C12	−1.5 (5)
C9—C6—C7—C8	0.6 (4)	C13—C12—C17—C16	1.0 (4)
C3—C6—C7—C8	−176.9 (3)	C11—C12—C17—C16	178.4 (3)
C6—C7—C8—N2	0.1 (5)	C15—C14—C18—O4	−1.2 (4)
C7—C6—C9—C10	−0.7 (4)	C13—C14—C18—O4	−179.0 (3)
C3—C6—C9—C10	176.7 (3)	C15—C14—C18—O3	177.7 (3)
C6—C9—C10—N2	0.1 (5)	C13—C14—C18—O3	−0.1 (4)
O2—C11—C12—C13	165.0 (3)	C2—C1—N1—C5	3.4 (5)
O1—C11—C12—C13	−14.8 (4)	C4—C5—N1—C1	−3.3 (5)
O2—C11—C12—C17	−12.3 (4)	C7—C8—N2—C10	−0.7 (5)
O1—C11—C12—C17	167.9 (2)	C9—C10—N2—C8	0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.82	1.86	2.684 (3)	179
O3—H3···N1i	0.82	1.88	2.674 (4)	164
C8—H8···O2	0.93	2.42	3.138 (4)	134
C8—H8···F1ii	0.93	2.48	3.101 (4)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.82	1.86	2.684 (3)	179
O3—H3⋯N1i	0.82	1.88	2.674 (4)	164
C8—H8⋯O2	0.93	2.42	3.138 (4)	134
C8—H8⋯F1ii	0.93	2.48	3.101 (4)	125

Symmetry codes: (i) ; (ii) .