4,4′-Bipyridyl
N,
N′-dioxide crystallizes with 3-hydroxy-2-naphthoic acid to give a centrosymmetric three-component adduct, C
10H
8N
2O
2·2C
11H
8O
3, 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
CCDC reference: 645582
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
C10H8N2O2·2C11H8O3 | 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) Å3 | Prism, yellow |
Z = 2 | 0.30 × 0.25 × 0.20 mm |
Data collection top
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 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.16 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C16i | 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—C16i | 121.65 (17) |
C6—C7—H7 | 120.2 | C15—C16—C16i | 122.29 (17) |
C7—C8—C10 | 120.73 (19) | | |
Symmetry code: (i) −x, −y+1, −z−1. |
Hydrogen-bond geometry (Å, º) top
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 |
Geometric parameters for weak hydrogen bonds and π–π 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. topD-H···A | D—H | H···A | D···A | D—H···A |
C14-H14···O1 | 0.95 | 2.496 | 3.389 (7) | 156 |
C12-H12···O2i | 0.95 | 2.467 | 3.204 (8) | 134 |
C13-H13···O4i | 0.95 | 2.522 | 3.362 (3) | 147 |
Cg1···Cg1ii | | 3.435a | 3.861 (4)b | 27c |
Cg1···Cg2ii | | 3.446 | 3.886 (3) | 27 |
Cg1···Cg3iii | | 3.492 | 3.712 (4) | 19 |
Cg2···Cg3iv | | 3.580 | 3.685 (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. |