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.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](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

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)

Crystal data

C10H8N2·C7H6O4	F(000) = 648
Mr = 310.30	Dx = 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) Å^3	0.32 × 0.20 × 0.08 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0824P)^2] where P = (Fo^2 + 2Fc^2)/3
3528 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1^i	0.82	1.82	2.6298 (15)	172
O3—H3A···O1	0.82	1.88	2.6003 (16)	146
O4—H4···N2^ii	0.82	1.98	2.7622 (19)	160
C15—H15···Cg1^iii	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.