4,4′-Bipyridyl N,N′-dioxide–3-hydroxy-2-naphthoic acid (1/2)

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.

Computing details

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)

Crystal data

C10H8N2O2·2C11H8O3	F(000) = 588
Mr = 564.54	Dx = 1.406 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7800 (16) Å	Cell parameters from 2490 reflections
b = 11.8800 (11) Å	θ = 2.1–27.5°
c = 11.4700 (15) Å	µ = 0.10 mm^−1
β = 114.820 (5)°	T = 293 K
V = 1333.2 (3) Å^3	Prism, yellow
Z = 2	0.30 × 0.25 × 0.20 mm

Data collection

Make, Model diffractometer	3038 independent reflections
Radiation source: fine-focus sealed tube	2226 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 14.6306 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
CCD profile fitting scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −10→15
Tmin = 0.839, Tmax = 1.000	l = −14→14
9907 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 0.1631P] where P = (Fo^2 + 2Fc^2)/3
3038 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.16 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
O1	0.18458 (15)	0.58214 (12)	0.09720 (13)	0.0740 (4)
O2	0.23290 (15)	0.40082 (11)	0.14199 (12)	0.0699 (4)
H2	0.1983	0.3959	0.0615	0.084*
O3	0.21240 (16)	0.71931 (11)	0.28290 (15)	0.0727 (4)
H3	0.1944	0.6991	0.2073	0.087*
O4	0.14552 (17)	0.32739 (12)	−0.08157 (12)	0.0787 (4)
N1	0.10763 (15)	0.37778 (12)	−0.19440 (12)	0.0516 (4)
C1	0.22627 (17)	0.50500 (15)	0.17531 (16)	0.0530 (4)
C2	0.27113 (15)	0.52152 (13)	0.31465 (15)	0.0452 (4)
C3	0.26163 (16)	0.62990 (14)	0.36358 (18)	0.0518 (4)
C4	0.30015 (17)	0.64514 (15)	0.49205 (18)	0.0563 (5)
H4	0.2940	0.7180	0.5234	0.068*
C5	0.3877 (2)	0.5660 (2)	0.7132 (2)	0.0692 (6)
H5	0.3831	0.6378	0.7476	0.083*
C6	0.4312 (2)	0.4754 (2)	0.79280 (19)	0.0758 (6)
H6	0.4566	0.4851	0.8821	0.091*
C7	0.43941 (19)	0.3681 (2)	0.74570 (18)	0.0692 (6)
H7	0.4696	0.3057	0.8027	0.083*
C8	0.40393 (16)	0.35361 (16)	0.61795 (16)	0.0562 (4)
H8	0.4099	0.2809	0.5861	0.067*
C9	0.31936 (15)	0.43305 (13)	0.39928 (15)	0.0453 (4)
H9	0.3267	0.3609	0.3670	0.054*
C10	0.35824 (15)	0.44576 (13)	0.53190 (15)	0.0456 (4)
C11	0.34909 (16)	0.55425 (15)	0.57941 (17)	0.0512 (4)
C12	0.09075 (19)	0.31387 (15)	−0.29611 (16)	0.0565 (4)
H12	0.1076	0.2352	−0.2850	0.068*
C13	0.04963 (17)	0.36008 (14)	−0.41559 (15)	0.0506 (4)
H13	0.0389	0.3131	−0.4862	0.061*
C14	0.08520 (18)	0.48919 (14)	−0.20824 (16)	0.0534 (4)
H14	0.0987	0.5343	−0.1355	0.064*
C15	0.04288 (17)	0.53811 (14)	−0.32708 (14)	0.0479 (4)
H15	0.0266	0.6169	−0.3356	0.057*
C16	0.02329 (14)	0.47465 (13)	−0.43554 (14)	0.0393 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0955 (10)	0.0649 (8)	0.0573 (8)	0.0086 (7)	0.0278 (7)	0.0211 (7)
O2	0.1061 (11)	0.0551 (8)	0.0407 (7)	−0.0036 (7)	0.0232 (7)	0.0032 (6)
O3	0.0900 (10)	0.0466 (7)	0.0819 (10)	0.0095 (7)	0.0366 (9)	0.0160 (7)
O4	0.1273 (12)	0.0646 (8)	0.0365 (7)	0.0148 (8)	0.0268 (7)	0.0139 (6)
N1	0.0641 (8)	0.0530 (8)	0.0358 (7)	0.0063 (7)	0.0191 (6)	0.0058 (6)
C1	0.0535 (9)	0.0552 (10)	0.0487 (10)	−0.0025 (8)	0.0197 (8)	0.0092 (8)
C2	0.0415 (8)	0.0458 (9)	0.0479 (9)	−0.0043 (7)	0.0184 (7)	0.0033 (7)
C3	0.0466 (9)	0.0451 (9)	0.0648 (11)	−0.0014 (7)	0.0244 (8)	0.0052 (8)
C4	0.0528 (10)	0.0487 (9)	0.0694 (12)	−0.0022 (8)	0.0277 (9)	−0.0095 (8)
C5	0.0628 (12)	0.0874 (15)	0.0592 (12)	−0.0030 (10)	0.0275 (9)	−0.0194 (11)
C6	0.0691 (12)	0.1143 (19)	0.0422 (10)	−0.0041 (12)	0.0215 (9)	−0.0063 (11)
C7	0.0623 (11)	0.0923 (16)	0.0486 (11)	−0.0015 (11)	0.0190 (9)	0.0117 (10)
C8	0.0519 (10)	0.0637 (11)	0.0481 (10)	−0.0023 (8)	0.0164 (8)	0.0053 (8)
C9	0.0443 (8)	0.0447 (8)	0.0451 (9)	−0.0030 (7)	0.0168 (7)	0.0000 (7)
C10	0.0376 (8)	0.0519 (9)	0.0452 (9)	−0.0049 (7)	0.0153 (7)	0.0008 (7)
C11	0.0404 (8)	0.0623 (10)	0.0520 (10)	−0.0042 (7)	0.0204 (7)	−0.0073 (8)
C12	0.0777 (12)	0.0469 (9)	0.0442 (9)	0.0154 (8)	0.0250 (8)	0.0051 (7)
C13	0.0665 (10)	0.0454 (9)	0.0388 (9)	0.0082 (8)	0.0212 (7)	0.0000 (7)
C14	0.0734 (11)	0.0471 (9)	0.0399 (9)	−0.0008 (8)	0.0240 (8)	−0.0029 (7)
C15	0.0642 (10)	0.0409 (8)	0.0391 (8)	−0.0042 (7)	0.0222 (7)	−0.0002 (6)
C16	0.0383 (7)	0.0434 (8)	0.0370 (8)	−0.0031 (6)	0.0167 (6)	0.0011 (6)

Geometric parameters (Å, º)

O1—C1	1.227 (2)	C6—H6	0.9500
O2—C1	1.306 (2)	C7—C8	1.361 (3)
O2—H2	0.8400	C7—H7	0.9500
O3—C3	1.362 (2)	C8—C10	1.417 (2)
O3—H3	0.8400	C8—H8	0.9500
O4—N1	1.3252 (17)	C9—C10	1.406 (2)
N1—C12	1.339 (2)	C9—H9	0.9500
N1—C14	1.343 (2)	C10—C11	1.419 (2)
C1—C2	1.476 (2)	C12—C13	1.366 (2)
C2—C9	1.376 (2)	C12—H12	0.9500
C2—C3	1.425 (2)	C13—C16	1.390 (2)
C3—C4	1.365 (3)	C13—H13	0.9500
C4—C11	1.416 (3)	C14—C15	1.372 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.361 (3)	C15—C16	1.393 (2)
C5—C11	1.418 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C16^i	1.476 (3)
C6—C7	1.402 (3)
C1—O2—H2	109.5	C7—C8—H8	119.6
C3—O3—H3	109.5	C10—C8—H8	119.6
O4—N1—C12	117.92 (14)	C2—C9—C10	122.27 (15)
O4—N1—C14	121.81 (14)	C2—C9—H9	118.9
C12—N1—C14	120.27 (14)	C10—C9—H9	118.9
O1—C1—O2	122.83 (17)	C9—C10—C8	121.96 (16)
O1—C1—C2	122.98 (17)	C9—C10—C11	118.41 (15)
O2—C1—C2	114.18 (14)	C8—C10—C11	119.62 (16)
C9—C2—C3	118.72 (15)	C4—C11—C5	122.94 (18)
C9—C2—C1	121.16 (15)	C4—C11—C10	119.10 (16)
C3—C2—C1	120.10 (15)	C5—C11—C10	117.95 (17)
O3—C3—C4	119.04 (16)	N1—C12—C13	120.96 (16)
O3—C3—C2	120.60 (16)	N1—C12—H12	119.5
C4—C3—C2	120.35 (16)	C13—C12—H12	119.5
C3—C4—C11	121.13 (16)	C12—C13—C16	121.11 (15)
C3—C4—H4	119.4	C12—C13—H13	119.4
C11—C4—H4	119.4	C16—C13—H13	119.4
C6—C5—C11	120.7 (2)	N1—C14—C15	120.22 (15)
C6—C5—H5	119.7	N1—C14—H14	119.9
C11—C5—H5	119.7	C15—C14—H14	119.9
C5—C6—C7	121.37 (19)	C14—C15—C16	121.38 (15)
C5—C6—H6	119.3	C14—C15—H15	119.3
C7—C6—H6	119.3	C16—C15—H15	119.3
C8—C7—C6	119.7 (2)	C13—C16—C15	116.06 (14)
C8—C7—H7	120.2	C13—C16—C16^i	121.65 (17)
C6—C7—H7	120.2	C15—C16—C16^i	122.29 (17)
C7—C8—C10	120.73 (19)

Symmetry code: (i) −x, −y+1, −z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.84	1.85	2.597 (2)	147
O2—H2···O4	0.84	1.70	2.489 (2)	155