4,4′-Bipyridine–2,4-dihydroxy­benzoic acid (1/1)

Wang, Z.-L.; Wei, L.-H.; Li, M.-X.

doi:10.1107/S160053680602201X

4,4′-Bipyridine–2,4-dihydroxybenzoic acid (1/1)

The title compound, C₁₀H₈N₂·C₇H₆O₄, consists of 4,4′-bipyridine and 2,4-dihydroxybenzoic acid molecules, which are linked via O–H

N hydrogen bonds, forming infinite one-dimensional chains. Adjacent chains are further linked into a two-dimensional structure by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602201X/ob2028sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680602201X/ob2028Isup2.hkl Contains datablock I

CCDC reference: 613790

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.002 Å
R factor = 0.056
wR factor = 0.155
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.109
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

4,4'-Bipyridine–2,4-dihydroxybenzoic acid (1/1) top

Crystal data top

C₁₀H₈N₂·C₇H₆O₄	F(000) = 648
M_r = 310.30	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3592 reflections
a = 6.6085 (8) Å	θ = 2.7–27.7°
b = 10.7724 (12) Å	µ = 0.10 mm⁻¹
c = 20.809 (2) Å	T = 292 K
β = 95.942 (2)°	Plate, colorless
V = 1473.4 (3) Å³	0.32 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2537 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.109
Graphite monochromator	θ_max = 28.3°, θ_min = 2.0°
0.3° ω scans	h = −8→8
12686 measured reflections	k = −13→14
3528 independent reflections	l = −27→27

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0824P)²] where P = (F_o² + 2F_c²)/3
3528 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5905 (2)	0.63261 (14)	0.17562 (7)	0.0350 (4)
C2	0.7047 (2)	0.73227 (15)	0.15548 (7)	0.0375 (4)
C3	0.8696 (3)	0.71044 (15)	0.11999 (8)	0.0408 (4)
H3	0.9451	0.7767	0.1066	0.049*
C4	0.9199 (2)	0.59049 (16)	0.10484 (7)	0.0406 (4)
C5	0.8075 (3)	0.49116 (15)	0.12448 (8)	0.0417 (4)
H5	0.8414	0.4105	0.1139	0.050*
C6	0.6461 (2)	0.51229 (15)	0.15958 (7)	0.0382 (4)
H6	0.5723	0.4452	0.1729	0.046*
C7	0.4150 (2)	0.65560 (15)	0.21211 (8)	0.0387 (4)
C8	0.9597 (3)	0.72219 (17)	0.30444 (8)	0.0441 (4)
H8	1.0278	0.7849	0.2848	0.053*
C9	0.8150 (3)	0.75540 (16)	0.34489 (7)	0.0416 (4)
H9	0.7863	0.8386	0.3518	0.050*
C10	0.7138 (2)	0.66310 (15)	0.37493 (7)	0.0355 (4)
C11	0.7581 (3)	0.54070 (16)	0.36078 (8)	0.0418 (4)
H11	0.6905	0.4758	0.3789	0.050*
C12	0.9036 (3)	0.51665 (16)	0.31944 (8)	0.0439 (4)
H12	0.9314	0.4344	0.3101	0.053*
C13	0.5655 (2)	0.69477 (16)	0.42184 (7)	0.0378 (4)
C14	0.5974 (3)	0.79666 (17)	0.46202 (8)	0.0437 (4)
H14	0.7110	0.8469	0.4600	0.052*
C15	0.4581 (3)	0.82285 (18)	0.50521 (8)	0.0478 (4)
H15	0.4832	0.8907	0.5325	0.057*
C16	0.2615 (3)	0.65878 (18)	0.47114 (9)	0.0553 (5)
H16	0.1454	0.6111	0.4739	0.066*
C17	0.3928 (3)	0.62381 (18)	0.42724 (8)	0.0488 (5)
H17	0.3662	0.5538	0.4016	0.059*
N1	1.0059 (2)	0.60501 (13)	0.29241 (6)	0.0402 (3)
N2	0.2911 (2)	0.75722 (15)	0.51007 (7)	0.0513 (4)
O1	0.3646 (2)	0.76133 (11)	0.22696 (6)	0.0560 (4)
O2	0.31697 (19)	0.55641 (11)	0.22725 (6)	0.0495 (3)
H2	0.2164	0.5768	0.2448	0.074*
O3	0.6629 (2)	0.85092 (10)	0.16904 (7)	0.0558 (4)
H3A	0.5643	0.8533	0.1899	0.084*
O4	1.0780 (2)	0.56469 (13)	0.07082 (6)	0.0575 (4)
H4	1.1204	0.6292	0.0561	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0339 (8)	0.0371 (8)	0.0351 (8)	0.0021 (6)	0.0085 (6)	0.0025 (6)
C2	0.0396 (9)	0.0353 (9)	0.0384 (8)	0.0016 (7)	0.0074 (7)	0.0012 (6)
C3	0.0395 (9)	0.0409 (9)	0.0441 (9)	−0.0062 (7)	0.0136 (7)	0.0037 (7)
C4	0.0354 (9)	0.0509 (10)	0.0370 (8)	0.0035 (7)	0.0107 (7)	0.0031 (7)
C5	0.0434 (10)	0.0382 (9)	0.0453 (8)	0.0061 (7)	0.0127 (7)	0.0017 (7)
C6	0.0380 (9)	0.0350 (8)	0.0429 (8)	−0.0008 (7)	0.0108 (7)	0.0033 (6)
C7	0.0377 (9)	0.0400 (10)	0.0400 (8)	0.0023 (7)	0.0109 (7)	0.0014 (6)
C8	0.0447 (10)	0.0471 (10)	0.0428 (9)	−0.0027 (8)	0.0156 (7)	0.0035 (7)
C9	0.0420 (9)	0.0370 (9)	0.0475 (9)	0.0006 (7)	0.0132 (7)	−0.0022 (7)
C10	0.0305 (8)	0.0433 (9)	0.0333 (7)	0.0001 (6)	0.0064 (6)	−0.0028 (6)
C11	0.0425 (10)	0.0393 (9)	0.0452 (9)	−0.0046 (7)	0.0129 (7)	−0.0003 (7)
C12	0.0451 (10)	0.0404 (9)	0.0480 (9)	0.0016 (7)	0.0131 (8)	−0.0059 (7)
C13	0.0332 (8)	0.0454 (9)	0.0358 (8)	0.0015 (7)	0.0083 (6)	−0.0010 (6)
C14	0.0370 (9)	0.0520 (10)	0.0434 (9)	−0.0050 (8)	0.0106 (7)	−0.0066 (7)
C15	0.0500 (11)	0.0556 (11)	0.0392 (9)	−0.0001 (9)	0.0115 (8)	−0.0092 (8)
C16	0.0440 (11)	0.0629 (13)	0.0626 (12)	−0.0111 (9)	0.0229 (9)	−0.0069 (9)
C17	0.0452 (10)	0.0520 (11)	0.0513 (10)	−0.0091 (8)	0.0148 (8)	−0.0105 (8)
N1	0.0372 (8)	0.0462 (8)	0.0389 (7)	0.0012 (6)	0.0119 (6)	−0.0040 (6)
N2	0.0469 (9)	0.0652 (10)	0.0448 (8)	−0.0007 (7)	0.0189 (7)	−0.0043 (7)
O1	0.0533 (8)	0.0405 (7)	0.0794 (9)	0.0026 (6)	0.0319 (7)	−0.0059 (6)
O2	0.0477 (7)	0.0437 (7)	0.0623 (8)	−0.0014 (5)	0.0311 (6)	0.0009 (5)
O3	0.0617 (9)	0.0332 (7)	0.0778 (9)	0.0003 (6)	0.0333 (7)	−0.0006 (6)
O4	0.0544 (8)	0.0595 (8)	0.0648 (8)	0.0031 (6)	0.0350 (7)	−0.0002 (7)

Geometric parameters (Å, º) top

C1—C6	1.397 (2)	C10—C11	1.389 (2)
C1—C2	1.401 (2)	C10—C13	1.4923 (19)
C1—C7	1.471 (2)	C11—C12	1.380 (2)
C2—O3	1.3438 (19)	C11—H11	0.9300
C2—C3	1.398 (2)	C12—N1	1.326 (2)
C3—C4	1.379 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.383 (2)
C4—O4	1.3502 (18)	C13—C17	1.388 (2)
C4—C5	1.388 (2)	C14—C15	1.380 (2)
C5—C6	1.372 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—N2	1.324 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—O1	1.2349 (18)	C16—N2	1.336 (2)
C7—O2	1.3049 (19)	C16—C17	1.376 (2)
C8—N1	1.329 (2)	C16—H16	0.9300
C8—C9	1.385 (2)	C17—H17	0.9300
C8—H8	0.9300	O2—H2	0.8200
C9—C10	1.383 (2)	O3—H3A	0.8200
C9—H9	0.9300	O4—H4	0.8200

C6—C1—C2	118.43 (13)	C9—C10—C13	120.81 (14)
C6—C1—C7	121.36 (13)	C11—C10—C13	121.52 (14)
C2—C1—C7	120.21 (14)	C12—C11—C10	119.09 (15)
O3—C2—C3	117.35 (14)	C12—C11—H11	120.5
O3—C2—C1	122.48 (13)	C10—C11—H11	120.5
C3—C2—C1	120.17 (14)	N1—C12—C11	123.27 (15)
C4—C3—C2	119.88 (14)	N1—C12—H12	118.4
C4—C3—H3	120.1	C11—C12—H12	118.4
C2—C3—H3	120.1	C14—C13—C17	117.59 (13)
O4—C4—C3	122.07 (14)	C14—C13—C10	120.53 (14)
O4—C4—C5	117.55 (15)	C17—C13—C10	121.88 (15)
C3—C4—C5	120.37 (13)	C15—C14—C13	119.08 (15)
C6—C5—C4	119.87 (14)	C15—C14—H14	120.5
C6—C5—H5	120.1	C13—C14—H14	120.5
C4—C5—H5	120.1	N2—C15—C14	123.93 (16)
C5—C6—C1	121.27 (14)	N2—C15—H15	118.0
C5—C6—H6	119.4	C14—C15—H15	118.0
C1—C6—H6	119.4	N2—C16—C17	123.84 (17)
O1—C7—O2	122.77 (13)	N2—C16—H16	118.1
O1—C7—C1	122.13 (14)	C17—C16—H16	118.1
O2—C7—C1	115.10 (13)	C16—C17—C13	118.90 (17)
N1—C8—C9	123.13 (15)	C16—C17—H17	120.5
N1—C8—H8	118.4	C13—C17—H17	120.5
C9—C8—H8	118.4	C12—N1—C8	117.71 (13)
C10—C9—C8	119.05 (15)	C15—N2—C16	116.64 (14)
C10—C9—H9	120.5	C7—O2—H2	109.5
C8—C9—H9	120.5	C2—O3—H3A	109.5
C9—C10—C11	117.67 (13)	C4—O4—H4	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	1.82	2.6298 (15)	172
O3—H3A···O1	0.82	1.88	2.6003 (16)	146
O4—H4···N2ⁱⁱ	0.82	1.98	2.7622 (19)	160
C15—H15···Cg1ⁱⁱⁱ	0.93	2.73	3.3328 (19)	124

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

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4,4′-Bipyridine–2,4-dihydroxy­benzoic acid (1/1)

Supporting information

Key indicators

checkCIF/PLATON results

4,4′-Bipyridine–2,4-dihydroxybenzoic acid (1/1)