7-[4-(5,7-Dimethyl-1,8-naphthyridin-2-yl-oxy)phen-oxy]-2,4-dimethyl-1,8-naphthyridine methanol disolvate.

The title compound, C(26)H(22)N(4)O(2)·2CH(3)OH, was synthesized and characterized by (1)H NMR spectroscopy and X-ray structure analysis. There is one half-mol-ecule in the asymmetric unit with a centre of symmetry located at the centre of the benzene ring. The two bridged naphthyridine ring systems are in an anti-parallel orientation. In the crystal structure, O-H⋯N, C-H⋯O and C-H⋯N inter-actions define the packing.

Related literature

For related literature, see: Ferrarini et al. (2004 ▶); Goswami & Mukherjee (1997 ▶); Hoock et al. (1999 ▶); Jin, Liu & Chen (2007 ▶); Jin, Chen & Wang (2007 ▶); Nabanita et al. (2006 ▶); Nakatani et al. (2000 ▶); Nakataniz et al. (2001 ▶); Newkome et al. (1981 ▶); Stuk et al. (2003 ▶); Gavrilova & Bosnich (2004 ▶).

Experimental

Crystal data

C26H22N4O2·2CH4O

M = 486.56

Triclinic,

a = 7.009 (3) Å

b = 9.244 (3) Å

c = 10.239 (4) Å

α = 78.679 (6)°

β = 79.653 (6)°

γ = 82.689 (6)°

V = 637.0 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.27 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEX CCD Diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.984

3379 measured reflections

2216 independent reflections

1236 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.163

S = 1.03

2216 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SMn class="Chemical">ART (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706549X/kp2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706549X/kp2143Isup2.hkl

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

C26H22N4O2·2CH4O	Z = 1
Mr = 486.56	F000 = 258
Triclinic, P1	Dx = 1.268 Mg m−3
a = 7.009 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.244 (3) Å	Cell parameters from 877 reflections
c = 10.239 (4) Å	θ = 2.3–24.7º
α = 78.679 (6)º	µ = 0.09 mm−1
β = 79.653 (6)º	T = 298 (2) K
γ = 82.689 (6)º	Block, colourless
V = 637.0 (4) Å3	0.27 × 0.24 × 0.19 mm

Bruker SMART APEX CCD Diffractometer	2216 independent reflections
Radiation source: fine-focus sealed tube	1236 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 298(2) K	θmax = 25.0º
phi and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→5
Tmin = 0.977, Tmax = 0.984	k = −10→10
3379 measured reflections	l = −11→12

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.2468P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2216 reflections	Δρmax = 0.27 e Å−3
163 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.3076 (3)	0.1993 (2)	0.6758 (2)	0.0483 (6)
N2	0.5387 (3)	0.2103 (2)	0.8040 (2)	0.0496 (6)
O1	0.0813 (3)	0.19512 (19)	0.5388 (2)	0.0619 (6)
O2	0.3944 (3)	0.5192 (2)	0.7759 (3)	0.0967 (10)
H2	0.4376	0.4317	0.7831	0.145*
C1	0.4486 (4)	0.1239 (3)	0.7453 (3)	0.0430 (7)
C2	0.6819 (4)	0.1463 (3)	0.8699 (3)	0.0529 (8)
C3	0.7375 (4)	−0.0058 (3)	0.8838 (3)	0.0570 (8)
H3	0.8371	−0.0463	0.9328	0.068*
C4	0.6492 (4)	−0.0972 (3)	0.8273 (3)	0.0521 (8)
C5	0.4982 (4)	−0.0297 (3)	0.7537 (3)	0.0437 (7)
C6	0.3930 (4)	−0.1050 (3)	0.6864 (3)	0.0530 (8)
H6	0.4195	−0.2068	0.6903	0.064*
C7	0.2544 (4)	−0.0296 (3)	0.6165 (3)	0.0557 (8)
H7	0.1844	−0.0778	0.5719	0.067*
C8	0.2194 (4)	0.1241 (3)	0.6135 (3)	0.0489 (7)
C9	0.7853 (5)	0.2444 (4)	0.9283 (4)	0.0748 (10)
H9A	0.7284	0.3448	0.9090	0.112*
H9B	0.9206	0.2389	0.8892	0.112*
H9C	0.7732	0.2123	1.0242	0.112*
C10	0.7114 (5)	−0.2600 (3)	0.8422 (4)	0.0768 (11)
H10A	0.6335	−0.3056	0.7965	0.115*
H10B	0.6944	−0.3037	0.9362	0.115*
H10C	0.8461	−0.2751	0.8035	0.115*
C11	0.1900 (4)	0.4419 (3)	0.4653 (3)	0.0532 (8)
H11	0.3177	0.4026	0.4418	0.064*
C12	0.0463 (4)	0.3504 (3)	0.5222 (3)	0.0470 (7)
C13	−0.1421 (4)	0.4064 (3)	0.5566 (3)	0.0498 (7)
H13	−0.2379	0.3428	0.5947	0.060*
C14	0.1928 (5)	0.5291 (4)	0.8034 (4)	0.0744 (10)
H14A	0.1519	0.4905	0.8970	0.112*
H14B	0.1452	0.4727	0.7488	0.112*
H14C	0.1418	0.6310	0.7834	0.112*

	U11	U22	U33	U12	U13	U23
N1	0.0538 (15)	0.0380 (13)	0.0556 (16)	−0.0017 (11)	−0.0224 (12)	−0.0039 (11)
N2	0.0545 (15)	0.0452 (13)	0.0511 (15)	−0.0090 (11)	−0.0184 (12)	−0.0019 (11)
O1	0.0721 (14)	0.0400 (11)	0.0834 (16)	0.0003 (10)	−0.0463 (12)	−0.0069 (10)
O2	0.0614 (16)	0.0542 (14)	0.176 (3)	−0.0057 (11)	−0.0178 (16)	−0.0239 (16)
C1	0.0442 (16)	0.0406 (15)	0.0437 (17)	−0.0039 (12)	−0.0123 (13)	−0.0015 (12)
C2	0.0496 (18)	0.0580 (19)	0.0515 (19)	−0.0095 (15)	−0.0141 (15)	−0.0026 (14)
C3	0.0475 (18)	0.065 (2)	0.056 (2)	0.0036 (15)	−0.0188 (15)	−0.0011 (15)
C4	0.0492 (18)	0.0499 (17)	0.0528 (19)	0.0061 (14)	−0.0097 (15)	−0.0040 (14)
C5	0.0427 (16)	0.0400 (15)	0.0458 (17)	−0.0005 (12)	−0.0083 (13)	−0.0024 (12)
C6	0.0608 (19)	0.0353 (15)	0.063 (2)	0.0006 (14)	−0.0152 (16)	−0.0075 (14)
C7	0.064 (2)	0.0426 (16)	0.067 (2)	−0.0048 (15)	−0.0239 (17)	−0.0114 (14)
C8	0.0507 (17)	0.0432 (16)	0.0535 (18)	−0.0017 (13)	−0.0204 (15)	−0.0014 (13)
C9	0.078 (2)	0.078 (2)	0.079 (3)	−0.0178 (19)	−0.038 (2)	−0.0080 (19)
C10	0.079 (2)	0.058 (2)	0.092 (3)	0.0232 (18)	−0.035 (2)	−0.0121 (18)
C11	0.0488 (18)	0.0544 (18)	0.055 (2)	0.0034 (14)	−0.0140 (15)	−0.0070 (14)
C12	0.0560 (19)	0.0397 (15)	0.0478 (18)	−0.0031 (14)	−0.0249 (15)	0.0005 (13)
C13	0.0481 (18)	0.0493 (17)	0.0497 (19)	−0.0110 (14)	−0.0121 (14)	0.0051 (13)
C14	0.070 (2)	0.074 (2)	0.084 (3)	−0.0051 (18)	−0.016 (2)	−0.0227 (19)

N1—C8	1.303 (3)	C7—C8	1.406 (4)
N1—C1	1.361 (3)	C7—H7	0.9300
N2—C2	1.322 (3)	C9—H9A	0.9600
N2—C1	1.361 (3)	C9—H9B	0.9600
O1—C8	1.364 (3)	C9—H9C	0.9600
O1—C12	1.406 (3)	C10—H10A	0.9600
O2—C14	1.385 (4)	C10—H10B	0.9600
O2—H2	0.8200	C10—H10C	0.9600
C1—C5	1.407 (4)	C11—C12	1.372 (4)
C2—C3	1.396 (4)	C11—C13i	1.383 (4)
C2—C9	1.498 (4)	C11—H11	0.9300
C3—C4	1.373 (4)	C12—C13	1.367 (4)
C3—H3	0.9300	C13—C11i	1.383 (4)
C4—C5	1.418 (4)	C13—H13	0.9300
C4—C10	1.499 (4)	C14—H14A	0.9600
C5—C6	1.416 (4)	C14—H14B	0.9600
C6—C7	1.350 (4)	C14—H14C	0.9600
C6—H6	0.9300
C8—N1—C1	117.3 (2)	C2—C9—H9A	109.5
C2—N2—C1	117.9 (2)	C2—C9—H9B	109.5
C8—O1—C12	119.3 (2)	H9A—C9—H9B	109.5
C14—O2—H2	109.5	C2—C9—H9C	109.5
N2—C1—N1	114.1 (2)	H9A—C9—H9C	109.5
N2—C1—C5	123.2 (2)	H9B—C9—H9C	109.5
N1—C1—C5	122.7 (2)	C4—C10—H10A	109.5
N2—C2—C3	122.1 (3)	C4—C10—H10B	109.5
N2—C2—C9	117.1 (3)	H10A—C10—H10B	109.5
C3—C2—C9	120.8 (3)	C4—C10—H10C	109.5
C4—C3—C2	121.9 (3)	H10A—C10—H10C	109.5
C4—C3—H3	119.1	H10B—C10—H10C	109.5
C2—C3—H3	119.1	C12—C11—C13i	119.0 (3)
C3—C4—C5	116.8 (3)	C12—C11—H11	120.5
C3—C4—C10	121.3 (3)	C13i—C11—H11	120.5
C5—C4—C10	122.0 (3)	C13—C12—C11	121.2 (2)
C1—C5—C6	116.9 (2)	C13—C12—O1	116.5 (2)
C1—C5—C4	118.2 (3)	C11—C12—O1	122.1 (3)
C6—C5—C4	124.9 (2)	C12—C13—C11i	119.8 (3)
C7—C6—C5	120.2 (3)	C12—C13—H13	120.1
C7—C6—H6	119.9	C11i—C13—H13	120.1
C5—C6—H6	119.9	O2—C14—H14A	109.5
C6—C7—C8	117.9 (3)	O2—C14—H14B	109.5
C6—C7—H7	121.1	H14A—C14—H14B	109.5
C8—C7—H7	121.1	O2—C14—H14C	109.5
N1—C8—O1	119.7 (2)	H14A—C14—H14C	109.5
N1—C8—C7	124.9 (2)	H14B—C14—H14C	109.5
O1—C8—C7	115.3 (2)
C2—N2—C1—N1	−177.8 (2)	C10—C4—C5—C6	−0.8 (5)
C2—N2—C1—C5	1.3 (4)	C1—C5—C6—C7	1.0 (4)
C8—N1—C1—N2	178.0 (2)	C4—C5—C6—C7	−178.5 (3)
C8—N1—C1—C5	−1.1 (4)	C5—C6—C7—C8	0.0 (5)
C1—N2—C2—C3	−2.0 (4)	C1—N1—C8—O1	−177.9 (2)
C1—N2—C2—C9	177.3 (3)	C1—N1—C8—C7	2.2 (4)
N2—C2—C3—C4	1.5 (5)	C12—O1—C8—N1	4.6 (4)
C9—C2—C3—C4	−177.8 (3)	C12—O1—C8—C7	−175.5 (3)
C2—C3—C4—C5	0.0 (4)	C6—C7—C8—N1	−1.7 (5)
C2—C3—C4—C10	179.5 (3)	C6—C7—C8—O1	178.5 (3)
N2—C1—C5—C6	−179.4 (3)	C13i—C11—C12—C13	0.3 (5)
N1—C1—C5—C6	−0.4 (4)	C13i—C11—C12—O1	175.5 (2)
N2—C1—C5—C4	0.1 (4)	C8—O1—C12—C13	−126.0 (3)
N1—C1—C5—C4	179.1 (3)	C8—O1—C12—C11	58.6 (4)
C3—C4—C5—C1	−0.7 (4)	C11—C12—C13—C11i	−0.3 (5)
C10—C4—C5—C1	179.7 (3)	O1—C12—C13—C11i	−175.7 (2)
C3—C4—C5—C6	178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	2.06	2.882 (3)	178
C6—H6···O2ii	0.93	2.53	3.414 (4)	159
C10—H10A···O2ii	0.96	2.54	3.436 (4)	156
C13—H13···N2iii	0.93	2.61	3.450 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	2.06	2.882 (3)	178
C6—H6⋯O2i	0.93	2.53	3.414 (4)	159
C10—H10A⋯O2i	0.96	2.54	3.436 (4)	156
C13—H13⋯N2ii	0.93	2.61	3.450 (4)	151

Symmetry codes: (i) ; (ii) .