4,4'-({[(Pyridine-2,6-di-yl)bis-(methyl-ene)]bis-(-oxy)}bis-(methyl-ene))dibenzo-nitrile.

The complete title molecule, C23H19N3O2, is generated by a twofold axis passing through the central ring. The two oxymethyl-benzo-nitrile arms are attached at the meta positions of the central pyridine ring. The dihedral angle between the pyridine ring and benzene ring of both arms is 84.55 (6)° while the benzene rings make a dihedral angle of 46.07 (7)°. In the crystal, weak C-H⋯π inter-actions link the molecules sheets parallel to the ac plane.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Lima et al. (2011 ▶); Wang & Zhao (2008 ▶): Zhao (2008 ▶); Xiao & Zhao (2008 ▶).

Experimental

Crystal data

C23H19N3O2

M = 369.41

Monoclinic,

a = 14.1838 (7) Å

b = 7.5493 (4) Å

c = 18.4619 (12) Å

β = 107.837 (2)°

V = 1881.83 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.49 × 0.44 × 0.34 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.972

21611 measured reflections

1846 independent reflections

1519 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.05

1846 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814000245/hg5373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000245/hg5373Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000245/hg5373Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C23H19N3O2	F(000) = 776
Mr = 369.41	Dx = 1.304 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8925 reflections
a = 14.1838 (7) Å	θ = 3.0–26.0°
b = 7.5493 (4) Å	µ = 0.09 mm−1
c = 18.4619 (12) Å	T = 296 K
β = 107.837 (2)°	Block, colourless
V = 1881.83 (18) Å3	0.49 × 0.44 × 0.34 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1846 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 83.66 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scan	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→9
Tmin = 0.960, Tmax = 0.972	l = −22→22
21611 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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.9538P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1846 reflections	Δρmax = 0.10 e Å−3
129 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0196 (14)

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.

	x	y	z	Uiso*/Ueq
O1	0.73355 (7)	0.39554 (16)	0.18488 (6)	0.0547 (3)
N1	1.0000	0.4615 (2)	0.2500	0.0416 (4)
N2	0.25164 (10)	0.0851 (2)	−0.08574 (9)	0.0706 (5)
C1	1.0000	0.0946 (3)	0.2500	0.0530 (6)
H1	1.0000	−0.0286	0.2500	0.064*
C2	0.91206 (10)	0.1866 (2)	0.23419 (8)	0.0495 (4)
H2	0.8519	0.1269	0.2230	0.059*
C3	0.91523 (9)	0.3697 (2)	0.23533 (7)	0.0415 (4)
C4	0.82379 (10)	0.4813 (2)	0.22471 (10)	0.0560 (4)
H4A	0.8206	0.5169	0.2744	0.067*
H4B	0.8300	0.5880	0.1973	0.067*
C5	0.71745 (10)	0.3882 (2)	0.10575 (8)	0.0463 (4)
H5A	0.7659	0.3102	0.0951	0.056*
H5B	0.7257	0.5054	0.0870	0.056*
C6	0.61510 (9)	0.32139 (17)	0.06575 (8)	0.0369 (3)
C7	0.58164 (10)	0.3218 (2)	−0.01320 (8)	0.0429 (4)
H7	0.6225	0.3645	−0.0402	0.052*
C8	0.48871 (11)	0.2599 (2)	−0.05204 (8)	0.0452 (4)
H8	0.4672	0.2599	−0.1050	0.054*
C9	0.42703 (10)	0.19725 (18)	−0.01217 (8)	0.0403 (3)
C10	0.45942 (10)	0.19748 (19)	0.06662 (8)	0.0443 (4)
H10	0.4182	0.1562	0.0936	0.053*
C11	0.55300 (10)	0.25913 (19)	0.10512 (8)	0.0422 (4)
H11	0.5746	0.2588	0.1580	0.051*
C12	0.32950 (11)	0.1331 (2)	−0.05269 (9)	0.0496 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0282 (5)	0.0835 (9)	0.0491 (6)	−0.0047 (5)	0.0069 (4)	−0.0156 (5)
N1	0.0293 (8)	0.0550 (10)	0.0369 (8)	0.000	0.0050 (6)	0.000
N2	0.0447 (8)	0.0701 (10)	0.0859 (11)	−0.0081 (7)	0.0035 (7)	−0.0136 (8)
C1	0.0554 (13)	0.0502 (13)	0.0511 (12)	0.000	0.0130 (10)	0.000
C2	0.0393 (8)	0.0624 (10)	0.0446 (8)	−0.0113 (7)	0.0095 (6)	−0.0047 (7)
C3	0.0302 (7)	0.0592 (9)	0.0329 (7)	−0.0029 (6)	0.0063 (5)	−0.0071 (6)
C4	0.0297 (7)	0.0736 (11)	0.0599 (9)	−0.0005 (7)	0.0065 (6)	−0.0220 (8)
C5	0.0327 (7)	0.0542 (9)	0.0498 (8)	0.0018 (6)	0.0095 (6)	−0.0016 (7)
C6	0.0302 (6)	0.0342 (7)	0.0442 (7)	0.0066 (5)	0.0084 (5)	−0.0003 (6)
C7	0.0403 (7)	0.0467 (8)	0.0441 (8)	0.0014 (6)	0.0164 (6)	−0.0001 (6)
C8	0.0469 (8)	0.0485 (8)	0.0368 (7)	0.0028 (7)	0.0080 (6)	−0.0030 (6)
C9	0.0343 (7)	0.0344 (7)	0.0478 (8)	0.0030 (5)	0.0061 (6)	−0.0013 (6)
C10	0.0368 (7)	0.0469 (8)	0.0500 (8)	0.0009 (6)	0.0142 (6)	0.0073 (6)
C11	0.0381 (7)	0.0480 (8)	0.0376 (7)	0.0046 (6)	0.0071 (6)	0.0040 (6)
C12	0.0419 (8)	0.0432 (8)	0.0588 (9)	0.0025 (7)	0.0080 (7)	−0.0039 (7)

O1—C5	1.4088 (18)	C5—H5A	0.9700
O1—C4	1.4217 (17)	C5—H5B	0.9700
N1—C3i	1.3417 (16)	C6—C11	1.3846 (19)
N1—C3	1.3417 (16)	C6—C7	1.3879 (19)
N2—C12	1.1449 (19)	C7—C8	1.3751 (19)
C1—C2	1.3786 (19)	C7—H7	0.9300
C1—C2i	1.3786 (19)	C8—C9	1.387 (2)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.382 (2)	C9—C10	1.3847 (19)
C2—H2	0.9300	C9—C12	1.4400 (19)
C3—C4	1.508 (2)	C10—C11	1.3804 (19)
C4—H4A	0.9700	C10—H10	0.9300
C4—H4B	0.9700	C11—H11	0.9300
C5—C6	1.5001 (18)
C5—O1—C4	112.87 (12)	C6—C5—H5B	109.6
C3i—N1—C3	117.77 (18)	H5A—C5—H5B	108.1
C2—C1—C2i	119.5 (2)	C11—C6—C7	118.96 (12)
C2—C1—H1	120.3	C11—C6—C5	122.07 (12)
C2i—C1—H1	120.3	C7—C6—C5	118.97 (12)
C1—C2—C3	118.50 (14)	C8—C7—C6	120.77 (13)
C1—C2—H2	120.8	C8—C7—H7	119.6
C3—C2—H2	120.8	C6—C7—H7	119.6
N1—C3—C2	122.86 (14)	C7—C8—C9	119.92 (13)
N1—C3—C4	114.79 (14)	C7—C8—H8	120.0
C2—C3—C4	122.25 (13)	C9—C8—H8	120.0
O1—C4—C3	114.53 (13)	C10—C9—C8	119.77 (12)
O1—C4—H4A	108.6	C10—C9—C12	120.20 (13)
C3—C4—H4A	108.6	C8—C9—C12	120.03 (13)
O1—C4—H4B	108.6	C11—C10—C9	119.91 (13)
C3—C4—H4B	108.6	C11—C10—H10	120.0
H4A—C4—H4B	107.6	C9—C10—H10	120.0
O1—C5—C6	110.41 (11)	C10—C11—C6	120.67 (13)
O1—C5—H5A	109.6	C10—C11—H11	119.7
C6—C5—H5A	109.6	C6—C11—H11	119.7
O1—C5—H5B	109.6	N2—C12—C9	178.67 (19)
C2i—C1—C2—C3	−0.50 (9)	C11—C6—C7—C8	−0.7 (2)
C3i—N1—C3—C2	−0.54 (10)	C5—C6—C7—C8	179.27 (13)
C3i—N1—C3—C4	175.99 (14)	C6—C7—C8—C9	0.5 (2)
C1—C2—C3—N1	1.1 (2)	C7—C8—C9—C10	0.0 (2)
C1—C2—C3—C4	−175.22 (11)	C7—C8—C9—C12	179.68 (14)
C5—O1—C4—C3	−76.99 (18)	C8—C9—C10—C11	−0.3 (2)
N1—C3—C4—O1	159.71 (12)	C12—C9—C10—C11	180.00 (13)
C2—C3—C4—O1	−23.7 (2)	C9—C10—C11—C6	0.1 (2)
C4—O1—C5—C6	−171.60 (12)	C7—C6—C11—C10	0.3 (2)
O1—C5—C6—C11	−6.58 (19)	C5—C6—C11—C10	−179.59 (13)
O1—C5—C6—C7	173.49 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1	0.93	2.39	2.735 (2)	102
C8—H8···Cgii	0.93	2.87	3.7180 (15)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C1–C3/C2′/C3′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg i	0.93	2.87	3.7180 (15)	152

Symmetry code: (i) .