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4,4′-Bipyridyl N,N′-dioxide crystallizes with 3-hydr­oxy-2-naphthoic acid to give a centrosymmetric three-component adduct, C10H8N2O2·2C11H8O3, which is engineered into a two-dimensional layer structure by two kinds of π–π inter­actions. Weak C—H...O inter­actions further link the two-dimensional structure into a three-dimensional structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107009717/av3073sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107009717/av3073Isup2.hkl
Contains datablock I

CCDC reference: 645582

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

4,4'-Bipyridyl N,N'-dioxide–3-hydroxy-2-naphthoic acid (1/2) top
Crystal data top
C10H8N2O2·2C11H8O3F(000) = 588
Mr = 564.54Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.7800 (16) ÅCell parameters from 2490 reflections
b = 11.8800 (11) Åθ = 2.1–27.5°
c = 11.4700 (15) ŵ = 0.10 mm1
β = 114.820 (5)°T = 293 K
V = 1333.2 (3) Å3Prism, yellow
Z = 20.30 × 0.25 × 0.20 mm
Data collection top
Make, Model
diffractometer
3038 independent reflections
Radiation source: fine-focus sealed tube2226 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 14.6306 pixels mm-1θmax = 27.5°, θmin = 2.6°
CCD profile fitting scansh = 1313
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)
k = 1015
Tmin = 0.839, Tmax = 1.000l = 1414
9907 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0668P)2 + 0.1631P]
where P = (Fo2 + 2Fc2)/3
3038 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
O10.18458 (15)0.58214 (12)0.09720 (13)0.0740 (4)
O20.23290 (15)0.40082 (11)0.14199 (12)0.0699 (4)
H20.19830.39590.06150.084*
O30.21240 (16)0.71931 (11)0.28290 (15)0.0727 (4)
H30.19440.69910.20730.087*
O40.14552 (17)0.32739 (12)0.08157 (12)0.0787 (4)
N10.10763 (15)0.37778 (12)0.19440 (12)0.0516 (4)
C10.22627 (17)0.50500 (15)0.17531 (16)0.0530 (4)
C20.27113 (15)0.52152 (13)0.31465 (15)0.0452 (4)
C30.26163 (16)0.62990 (14)0.36358 (18)0.0518 (4)
C40.30015 (17)0.64514 (15)0.49205 (18)0.0563 (5)
H40.29400.71800.52340.068*
C50.3877 (2)0.5660 (2)0.7132 (2)0.0692 (6)
H50.38310.63780.74760.083*
C60.4312 (2)0.4754 (2)0.79280 (19)0.0758 (6)
H60.45660.48510.88210.091*
C70.43941 (19)0.3681 (2)0.74570 (18)0.0692 (6)
H70.46960.30570.80270.083*
C80.40393 (16)0.35361 (16)0.61795 (16)0.0562 (4)
H80.40990.28090.58610.067*
C90.31936 (15)0.43305 (13)0.39928 (15)0.0453 (4)
H90.32670.36090.36700.054*
C100.35824 (15)0.44576 (13)0.53190 (15)0.0456 (4)
C110.34909 (16)0.55425 (15)0.57941 (17)0.0512 (4)
C120.09075 (19)0.31387 (15)0.29611 (16)0.0565 (4)
H120.10760.23520.28500.068*
C130.04963 (17)0.36008 (14)0.41559 (15)0.0506 (4)
H130.03890.31310.48620.061*
C140.08520 (18)0.48919 (14)0.20824 (16)0.0534 (4)
H140.09870.53430.13550.064*
C150.04288 (17)0.53811 (14)0.32708 (14)0.0479 (4)
H150.02660.61690.33560.057*
C160.02329 (14)0.47465 (13)0.43554 (14)0.0393 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0955 (10)0.0649 (8)0.0573 (8)0.0086 (7)0.0278 (7)0.0211 (7)
O20.1061 (11)0.0551 (8)0.0407 (7)0.0036 (7)0.0232 (7)0.0032 (6)
O30.0900 (10)0.0466 (7)0.0819 (10)0.0095 (7)0.0366 (9)0.0160 (7)
O40.1273 (12)0.0646 (8)0.0365 (7)0.0148 (8)0.0268 (7)0.0139 (6)
N10.0641 (8)0.0530 (8)0.0358 (7)0.0063 (7)0.0191 (6)0.0058 (6)
C10.0535 (9)0.0552 (10)0.0487 (10)0.0025 (8)0.0197 (8)0.0092 (8)
C20.0415 (8)0.0458 (9)0.0479 (9)0.0043 (7)0.0184 (7)0.0033 (7)
C30.0466 (9)0.0451 (9)0.0648 (11)0.0014 (7)0.0244 (8)0.0052 (8)
C40.0528 (10)0.0487 (9)0.0694 (12)0.0022 (8)0.0277 (9)0.0095 (8)
C50.0628 (12)0.0874 (15)0.0592 (12)0.0030 (10)0.0275 (9)0.0194 (11)
C60.0691 (12)0.1143 (19)0.0422 (10)0.0041 (12)0.0215 (9)0.0063 (11)
C70.0623 (11)0.0923 (16)0.0486 (11)0.0015 (11)0.0190 (9)0.0117 (10)
C80.0519 (10)0.0637 (11)0.0481 (10)0.0023 (8)0.0164 (8)0.0053 (8)
C90.0443 (8)0.0447 (8)0.0451 (9)0.0030 (7)0.0168 (7)0.0000 (7)
C100.0376 (8)0.0519 (9)0.0452 (9)0.0049 (7)0.0153 (7)0.0008 (7)
C110.0404 (8)0.0623 (10)0.0520 (10)0.0042 (7)0.0204 (7)0.0073 (8)
C120.0777 (12)0.0469 (9)0.0442 (9)0.0154 (8)0.0250 (8)0.0051 (7)
C130.0665 (10)0.0454 (9)0.0388 (9)0.0082 (8)0.0212 (7)0.0000 (7)
C140.0734 (11)0.0471 (9)0.0399 (9)0.0008 (8)0.0240 (8)0.0029 (7)
C150.0642 (10)0.0409 (8)0.0391 (8)0.0042 (7)0.0222 (7)0.0002 (6)
C160.0383 (7)0.0434 (8)0.0370 (8)0.0031 (6)0.0167 (6)0.0011 (6)
Geometric parameters (Å, º) top
O1—C11.227 (2)C6—H60.9500
O2—C11.306 (2)C7—C81.361 (3)
O2—H20.8400C7—H70.9500
O3—C31.362 (2)C8—C101.417 (2)
O3—H30.8400C8—H80.9500
O4—N11.3252 (17)C9—C101.406 (2)
N1—C121.339 (2)C9—H90.9500
N1—C141.343 (2)C10—C111.419 (2)
C1—C21.476 (2)C12—C131.366 (2)
C2—C91.376 (2)C12—H120.9500
C2—C31.425 (2)C13—C161.390 (2)
C3—C41.365 (3)C13—H130.9500
C4—C111.416 (3)C14—C151.372 (2)
C4—H40.9500C14—H140.9500
C5—C61.361 (3)C15—C161.393 (2)
C5—C111.418 (3)C15—H150.9500
C5—H50.9500C16—C16i1.476 (3)
C6—C71.402 (3)
C1—O2—H2109.5C7—C8—H8119.6
C3—O3—H3109.5C10—C8—H8119.6
O4—N1—C12117.92 (14)C2—C9—C10122.27 (15)
O4—N1—C14121.81 (14)C2—C9—H9118.9
C12—N1—C14120.27 (14)C10—C9—H9118.9
O1—C1—O2122.83 (17)C9—C10—C8121.96 (16)
O1—C1—C2122.98 (17)C9—C10—C11118.41 (15)
O2—C1—C2114.18 (14)C8—C10—C11119.62 (16)
C9—C2—C3118.72 (15)C4—C11—C5122.94 (18)
C9—C2—C1121.16 (15)C4—C11—C10119.10 (16)
C3—C2—C1120.10 (15)C5—C11—C10117.95 (17)
O3—C3—C4119.04 (16)N1—C12—C13120.96 (16)
O3—C3—C2120.60 (16)N1—C12—H12119.5
C4—C3—C2120.35 (16)C13—C12—H12119.5
C3—C4—C11121.13 (16)C12—C13—C16121.11 (15)
C3—C4—H4119.4C12—C13—H13119.4
C11—C4—H4119.4C16—C13—H13119.4
C6—C5—C11120.7 (2)N1—C14—C15120.22 (15)
C6—C5—H5119.7N1—C14—H14119.9
C11—C5—H5119.7C15—C14—H14119.9
C5—C6—C7121.37 (19)C14—C15—C16121.38 (15)
C5—C6—H6119.3C14—C15—H15119.3
C7—C6—H6119.3C16—C15—H15119.3
C8—C7—C6119.7 (2)C13—C16—C15116.06 (14)
C8—C7—H7120.2C13—C16—C16i121.65 (17)
C6—C7—H7120.2C15—C16—C16i122.29 (17)
C7—C8—C10120.73 (19)
Symmetry code: (i) x, y+1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.841.852.597 (2)147
O2—H2···O40.841.702.489 (2)155
Geometric parameters for weak hydrogen bonds and ππ interactions (Å, °) Cg1 is the centroid of the ring C2–C4/C11/C10/C9. Cg2 is the centroid of the ring C5–C8/C10/C11. Cg3 is the centroid of the ring N1/C12/C13/C16/C15/C14. top
D-H···AD—HH···AD···AD—H···A
C14-H14···O10.952.4963.389 (7)156
C12-H12···O2i0.952.4673.204 (8)134
C13-H13···O4i0.952.5223.362 (3)147
Cg1···Cg1ii3.435a3.861 (4)b27c
Cg1···Cg2ii3.4463.886 (3)27
Cg1···Cg3iii3.4923.712 (4)19
Cg2···Cg3iv3.5803.685 (5)13
(a) Perpendicular distance between Cgx and Cgy. (b) Distance between ring centroids. (c) Angle between the Cgx···Cgy vector and the normal to the plane of Cgy Symmetry codes:(i) x, 1/2-y, z-1/2; (ii) 1-x, 1-y, 1-z; (iii) -x, 1-y, -z; (iv) x, y, 1+z.
 

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