3-(4-Hy-droxy-phen-yl)-1,5-bis-(pyridin-2-yl)pentane-1,5-dione.

In the title mol-ecule, C21H18N2O3, the pyridine rings make a dihedral angle of 13.1 (1)°. The phenyl ring is approximately perpendicular to both of them, forming dihedral angles of 87.4 (1)and 81.9 (1)°. In the crystal, pairs of O-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric dimers. Additional C-H⋯O, π-π [centroid-centroid distance = 3.971 (2) Å] and C-H⋯π inter-actions consolidate the dimers into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Constable et al. (1990 ▶, 1998 ▶); He et al. (2006 ▶). For the syntheses of terpyridine compounds and their properties and applications, see: Ma et al. (2009 ▶, 2010 ▶, 2012 ▶, 2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H18N2O3

M = 346.37

Triclinic,

a = 8.4392 (6) Å

b = 10.6683 (7) Å

c = 11.0755 (8) Å

α = 100.623 (6)°

β = 103.867 (6)°

γ = 110.550 (6)°

V = 866.05 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.39 × 0.38 × 0.22 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2012 ▶) T min = 0.813, T max = 1.000

6339 measured reflections

3544 independent reflections

2661 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.03

3544 reflections

308 parameters

All H-atom parameters refined

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, C21H18N2O3. DOI: 10.1107/S1600536813025518/ld2113sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025518/ld2113Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025518/ld2113Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18N2O3	Z = 2
Mr = 346.37	F(000) = 364
Triclinic, P1	Dx = 1.328 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4392 (6) Å	Cell parameters from 6339 reflections
b = 10.6683 (7) Å	θ = 3.2–26.4°
c = 11.0755 (8) Å	µ = 0.09 mm−1
α = 100.623 (6)°	T = 298 K
β = 103.867 (6)°	Prism, colourless
γ = 110.550 (6)°	0.39 × 0.38 × 0.22 mm
V = 866.05 (10) Å3

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3544 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2661 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 0 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2012)	k = −13→13
Tmin = 0.813, Tmax = 1.000	l = −13→11
6339 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	All H-atom parameters refined
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.1436P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3544 reflections	Δρmax = 0.18 e Å−3
308 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	0.71359 (19)	0.30614 (12)	0.46604 (11)	0.0618 (4)
O2	0.91770 (19)	0.78344 (12)	0.42074 (12)	0.0667 (4)
O3	0.08708 (17)	0.40522 (14)	0.08964 (13)	0.0592 (3)
H03A	0.044 (3)	0.351 (3)	0.003 (2)	0.100 (8)*
N1	0.6613 (2)	0.06026 (14)	0.18572 (13)	0.0603 (4)
N2	1.06938 (19)	0.81798 (14)	0.15318 (13)	0.0493 (4)
C1	0.6711 (2)	0.10690 (15)	0.30835 (14)	0.0409 (4)
C2	0.6203 (3)	0.01932 (17)	0.38203 (17)	0.0545 (5)
H2A	0.632 (2)	0.0607 (19)	0.4701 (18)	0.060 (5)*
C3	0.5570 (3)	−0.12308 (18)	0.32835 (19)	0.0639 (5)
H3A	0.524 (3)	−0.184 (2)	0.3782 (19)	0.078 (6)*
C4	0.5449 (3)	−0.17259 (19)	0.20295 (19)	0.0680 (6)
H4A	0.501 (3)	−0.273 (2)	0.159 (2)	0.083 (6)*
C5	0.5963 (4)	−0.07886 (19)	0.1355 (2)	0.0791 (7)
H5A	0.586 (3)	−0.110 (2)	0.044 (2)	0.092 (7)*
C6	0.7379 (2)	0.26254 (15)	0.36597 (14)	0.0414 (4)
C7	0.8359 (2)	0.35918 (16)	0.29975 (17)	0.0432 (4)
H7A	0.966 (3)	0.3793 (18)	0.3406 (17)	0.060 (5)*
H7B	0.798 (2)	0.3108 (17)	0.2046 (16)	0.049 (4)*
C8	0.8128 (2)	0.49738 (14)	0.32322 (14)	0.0378 (3)
H8A	0.847 (2)	0.5387 (15)	0.4188 (15)	0.040 (4)*
C9	0.9371 (2)	0.60196 (15)	0.27268 (16)	0.0409 (4)
H9B	1.059 (2)	0.6076 (17)	0.2993 (15)	0.052 (5)*
H9A	0.897 (2)	0.5730 (17)	0.1737 (17)	0.052 (5)*
C10	0.9588 (2)	0.74944 (15)	0.32631 (15)	0.0426 (4)
C11	1.0436 (2)	0.85928 (15)	0.26587 (15)	0.0428 (4)
C12	1.0940 (3)	0.99903 (18)	0.3296 (2)	0.0623 (5)
H12A	1.072 (3)	1.023 (2)	0.410 (2)	0.075 (6)*
C13	1.1764 (3)	1.0996 (2)	0.2766 (2)	0.0798 (7)
H13A	1.215 (3)	1.200 (3)	0.322 (2)	0.108 (8)*
C14	1.2058 (3)	1.0592 (2)	0.1633 (2)	0.0808 (7)
H14A	1.263 (3)	1.123 (3)	0.122 (2)	0.100 (8)*
C15	1.1504 (3)	0.9187 (2)	0.1043 (2)	0.0665 (5)
H15A	1.167 (3)	0.886 (2)	0.0226 (19)	0.068 (6)*
C16	0.6193 (2)	0.47157 (13)	0.26132 (13)	0.0352 (3)
C17	0.5210 (2)	0.51095 (15)	0.33320 (15)	0.0404 (4)
H17A	0.582 (2)	0.5549 (16)	0.4262 (16)	0.047 (4)*
C18	0.3451 (2)	0.48794 (16)	0.27609 (15)	0.0439 (4)
H18A	0.281 (2)	0.5150 (18)	0.3262 (16)	0.055 (5)*
C19	0.2610 (2)	0.42459 (15)	0.14348 (15)	0.0412 (4)
C20	0.3557 (2)	0.38460 (16)	0.06964 (15)	0.0431 (4)
H20A	0.297 (2)	0.3412 (18)	−0.0231 (17)	0.056 (5)*
C21	0.5317 (2)	0.40803 (15)	0.12846 (14)	0.0412 (4)
H21A	0.598 (2)	0.3788 (17)	0.0732 (16)	0.052 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0992 (11)	0.0463 (6)	0.0503 (7)	0.0314 (7)	0.0388 (7)	0.0165 (5)
O2	0.0913 (11)	0.0402 (6)	0.0726 (8)	0.0205 (6)	0.0498 (8)	0.0096 (6)
O3	0.0476 (8)	0.0696 (8)	0.0573 (8)	0.0270 (6)	0.0158 (6)	0.0081 (6)
N1	0.0922 (13)	0.0422 (8)	0.0493 (8)	0.0227 (8)	0.0355 (8)	0.0142 (6)
N2	0.0491 (9)	0.0450 (7)	0.0508 (8)	0.0142 (6)	0.0180 (6)	0.0160 (6)
C1	0.0478 (10)	0.0381 (8)	0.0402 (8)	0.0191 (7)	0.0162 (7)	0.0144 (6)
C2	0.0769 (13)	0.0433 (9)	0.0463 (9)	0.0213 (9)	0.0281 (9)	0.0168 (8)
C3	0.0923 (16)	0.0427 (9)	0.0621 (11)	0.0231 (10)	0.0357 (11)	0.0241 (9)
C4	0.0978 (17)	0.0371 (9)	0.0669 (12)	0.0208 (10)	0.0369 (11)	0.0125 (9)
C5	0.132 (2)	0.0432 (10)	0.0587 (12)	0.0238 (11)	0.0485 (13)	0.0097 (9)
C6	0.0495 (10)	0.0409 (8)	0.0380 (8)	0.0218 (7)	0.0156 (7)	0.0135 (7)
C7	0.0499 (11)	0.0369 (8)	0.0492 (9)	0.0206 (7)	0.0211 (8)	0.0152 (7)
C8	0.0438 (9)	0.0325 (7)	0.0377 (8)	0.0152 (6)	0.0161 (7)	0.0093 (6)
C9	0.0419 (10)	0.0329 (7)	0.0491 (9)	0.0140 (7)	0.0199 (7)	0.0108 (7)
C10	0.0423 (9)	0.0346 (7)	0.0472 (8)	0.0126 (7)	0.0172 (7)	0.0075 (7)
C11	0.0404 (9)	0.0348 (7)	0.0496 (9)	0.0133 (7)	0.0132 (7)	0.0110 (7)
C12	0.0771 (14)	0.0387 (9)	0.0689 (12)	0.0200 (9)	0.0284 (11)	0.0131 (9)
C13	0.1020 (18)	0.0371 (10)	0.0973 (16)	0.0189 (11)	0.0391 (14)	0.0247 (11)
C14	0.0974 (18)	0.0550 (12)	0.0934 (16)	0.0188 (11)	0.0427 (14)	0.0405 (12)
C15	0.0765 (15)	0.0599 (11)	0.0652 (12)	0.0200 (10)	0.0317 (11)	0.0285 (10)
C16	0.0438 (9)	0.0261 (6)	0.0379 (7)	0.0128 (6)	0.0182 (6)	0.0112 (6)
C17	0.0494 (10)	0.0371 (7)	0.0351 (8)	0.0163 (7)	0.0183 (7)	0.0092 (6)
C18	0.0475 (10)	0.0432 (8)	0.0465 (9)	0.0205 (7)	0.0246 (8)	0.0102 (7)
C19	0.0417 (9)	0.0358 (7)	0.0475 (8)	0.0154 (7)	0.0174 (7)	0.0133 (7)
C20	0.0466 (10)	0.0410 (8)	0.0366 (8)	0.0135 (7)	0.0153 (7)	0.0071 (7)
C21	0.0464 (10)	0.0385 (8)	0.0405 (8)	0.0164 (7)	0.0222 (7)	0.0078 (6)

O1—C6	1.2135 (17)	C8—H8A	0.996 (15)
O2—C10	1.2114 (18)	C9—C10	1.504 (2)
O3—C19	1.3689 (19)	C9—H9B	0.975 (18)
O3—H03A	0.93 (2)	C9—H9A	1.017 (17)
N1—C1	1.3295 (19)	C10—C11	1.504 (2)
N1—C5	1.338 (2)	C11—C12	1.387 (2)
N2—C15	1.339 (2)	C12—C13	1.372 (3)
N2—C11	1.340 (2)	C12—H12A	0.96 (2)
C1—C2	1.375 (2)	C13—C14	1.360 (3)
C1—C6	1.504 (2)	C13—H13A	0.99 (3)
C2—C3	1.375 (2)	C14—C15	1.376 (3)
C2—H2A	0.960 (18)	C14—H14A	0.95 (3)
C3—C4	1.357 (3)	C15—H15A	0.966 (19)
C3—H3A	0.94 (2)	C16—C21	1.389 (2)
C4—C5	1.368 (3)	C16—C17	1.391 (2)
C4—H4A	0.99 (2)	C17—C18	1.378 (2)
C5—H5A	0.99 (2)	C17—H17A	0.971 (16)
C6—C7	1.502 (2)	C18—C19	1.384 (2)
C7—C8	1.538 (2)	C18—H18A	0.938 (18)
C7—H7A	1.006 (19)	C19—C20	1.384 (2)
C7—H7B	1.001 (16)	C20—C21	1.381 (2)
C8—C16	1.513 (2)	C20—H20A	0.967 (17)
C8—C9	1.532 (2)	C21—H21A	0.998 (17)
C19—O3—H03A	109.1 (15)	H9B—C9—H9A	104.6 (13)
C1—N1—C5	116.28 (15)	O2—C10—C9	121.67 (14)
C15—N2—C11	116.90 (15)	O2—C10—C11	119.15 (13)
N1—C1—C2	122.88 (14)	C9—C10—C11	119.08 (13)
N1—C1—C6	117.47 (13)	N2—C11—C12	122.63 (15)
C2—C1—C6	119.64 (14)	N2—C11—C10	118.46 (13)
C1—C2—C3	119.43 (16)	C12—C11—C10	118.91 (15)
C1—C2—H2A	118.1 (11)	C13—C12—C11	119.0 (2)
C3—C2—H2A	122.4 (11)	C13—C12—H12A	121.8 (12)
C4—C3—C2	118.47 (17)	C11—C12—H12A	119.2 (12)
C4—C3—H3A	121.3 (12)	C14—C13—C12	118.97 (19)
C2—C3—H3A	120.2 (12)	C14—C13—H13A	121.0 (15)
C3—C4—C5	118.65 (17)	C12—C13—H13A	120.0 (15)
C3—C4—H4A	122.3 (12)	C13—C14—C15	119.1 (2)
C5—C4—H4A	119.1 (12)	C13—C14—H14A	123.3 (14)
N1—C5—C4	124.27 (18)	C15—C14—H14A	117.6 (15)
N1—C5—H5A	114.4 (13)	N2—C15—C14	123.4 (2)
C4—C5—H5A	121.3 (13)	N2—C15—H15A	115.5 (12)
O1—C6—C7	122.05 (14)	C14—C15—H15A	121.1 (12)
O1—C6—C1	118.79 (14)	C21—C16—C17	116.72 (14)
C7—C6—C1	119.14 (13)	C21—C16—C8	121.07 (13)
C6—C7—C8	112.24 (13)	C17—C16—C8	122.21 (13)
C6—C7—H7A	104.7 (10)	C18—C17—C16	121.93 (14)
C8—C7—H7A	109.3 (10)	C18—C17—H17A	121.3 (9)
C6—C7—H7B	110.5 (9)	C16—C17—H17A	116.7 (10)
C8—C7—H7B	111.5 (9)	C17—C18—C19	120.22 (15)
H7A—C7—H7B	108.3 (14)	C17—C18—H18A	120.7 (10)
C16—C8—C9	110.96 (12)	C19—C18—H18A	119.0 (11)
C16—C8—C7	110.90 (12)	O3—C19—C20	122.26 (14)
C9—C8—C7	110.75 (12)	O3—C19—C18	118.70 (14)
C16—C8—H8A	107.9 (9)	C20—C19—C18	119.04 (15)
C9—C8—H8A	108.1 (9)	C21—C20—C19	119.99 (14)
C7—C8—H8A	108.1 (8)	C21—C20—H20A	121.1 (10)
C10—C9—C8	112.42 (13)	C19—C20—H20A	118.9 (10)
C10—C9—H9B	104.4 (10)	C20—C21—C16	122.10 (14)
C8—C9—H9B	112.2 (10)	C20—C21—H21A	118.6 (9)
C10—C9—H9A	110.8 (9)	C16—C21—H21A	119.3 (10)
C8—C9—H9A	111.9 (10)
C5—N1—C1—C2	0.8 (3)	C9—C10—C11—N2	11.1 (2)
C5—N1—C1—C6	−178.05 (18)	O2—C10—C11—C12	8.4 (3)
N1—C1—C2—C3	0.3 (3)	C9—C10—C11—C12	−168.07 (16)
C6—C1—C2—C3	179.14 (17)	N2—C11—C12—C13	−1.1 (3)
C1—C2—C3—C4	−0.7 (3)	C10—C11—C12—C13	178.02 (18)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C14	0.1 (4)
C1—N1—C5—C4	−1.6 (4)	C12—C13—C14—C15	0.7 (4)
C3—C4—C5—N1	1.1 (4)	C11—N2—C15—C14	−0.4 (3)
N1—C1—C6—O1	164.80 (16)	C13—C14—C15—N2	−0.6 (4)
C2—C1—C6—O1	−14.1 (2)	C9—C8—C16—C21	64.71 (16)
N1—C1—C6—C7	−16.5 (2)	C7—C8—C16—C21	−58.83 (17)
C2—C1—C6—C7	164.56 (16)	C9—C8—C16—C17	−114.63 (14)
O1—C6—C7—C8	−30.0 (2)	C7—C8—C16—C17	121.83 (14)
C1—C6—C7—C8	151.38 (14)	C21—C16—C17—C18	0.2 (2)
C6—C7—C8—C16	−65.15 (17)	C8—C16—C17—C18	179.58 (13)
C6—C7—C8—C9	171.20 (13)	C16—C17—C18—C19	−0.3 (2)
C16—C8—C9—C10	72.76 (16)	C17—C18—C19—O3	−179.03 (13)
C7—C8—C9—C10	−163.62 (14)	C17—C18—C19—C20	0.2 (2)
C8—C9—C10—O2	16.4 (2)	O3—C19—C20—C21	179.21 (13)
C8—C9—C10—C11	−167.22 (13)	C18—C19—C20—C21	0.0 (2)
C15—N2—C11—C12	1.2 (3)	C19—C20—C21—C16	−0.1 (2)
C15—N2—C11—C10	−177.89 (16)	C17—C16—C21—C20	0.0 (2)
O2—C10—C11—N2	−172.47 (15)	C8—C16—C21—C20	−179.38 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H03A···N2i	0.93 (2)	2.00 (2)	2.8940 (19)	160 (2)
C12—H12A···O2ii	0.96 (2)	2.48 (2)	3.312 (3)	145 (2)
C4a—H4a···Cg3iii	0.99 (2)	0.98 (2)	3.825 (2)	144 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H03A⋯N2i	0.93 (2)	2.00 (2)	2.8940 (19)	160 (2)
C12—H12A⋯O2ii	0.96 (2)	2.48 (2)	3.312 (3)	145 (2)
C4a—H4a⋯Cg3iii	0.99 (2)	0.98 (2)	3.825 (2)	144 (2)

Symmetry codes: (i) ; (ii) ; (iii) .