2,9-Bis(4-pyridylmeth­oxy)-1,10-phenanthroline

Zhang, S.G.; Xie, L.M.; Li, H.

doi:10.1107/S1600536809038318

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2549

doi:10.1107/S1600536809038318

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2,9-Bis(4-pyridylmethoxy)-1,10-phenanthroline

Shi Guo Zhang,^a ^* Long Miao Xie ^b and Hong Li ^a

^aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: zhangshiguo1970@yahoo.com.cn

(Received 14 September 2009; accepted 21 September 2009; online 26 September 2009)

In the title molecule, C₂₄H₁₈N₄O₂, the dihedral angles between the mean plane of the phenanthroline ring system and the pyridine rings are 82.52 (5) and 71.58 (4)°. The dihedral angle between the two pyridine ring planes is 53.54 (6)°. In the crystal structure, there are π–π stacking interactions between 1,10-phenanthroline rings, with centroid–centroid distances of 3.6101 (11) and 3.5864 (11) Å.

Related literature

For related structures, see: Liu et al. (2008 ); Zhang & Hou (2008 ).

Experimental

Crystal data

C₂₄H₁₈N₄O₂
M_r = 394.42
Monoclinic, P 2₁ /c
a = 12.701 (2) Å
b = 16.418 (3) Å
c = 9.7443 (16) Å
β = 107.535 (2)°
V = 1937.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.51 × 0.40 × 0.38 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.967
9860 measured reflections
3530 independent reflections
2603 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.03
3530 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038318/lh2907sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038318/lh2907Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry and a number of the derivatives (e.g. Liu et al., 2008; Zhang et al. 2008) have been synthesized and used as ligands to prepare new complexes. Herein we report the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. There are two π–π stacking interactions involving 1,10-phenathroline ring systems, one involving symmetry related pyridine rings with the relevant distances being Cg1···Cg2ⁱ = 3.6101 (11) Å and Cg1···Cg2ⁱ_perp = 3.373 Å and α = 1.63°; another from the adjacent pyridine rings and the benzene rings with the relevant distances being Cg2···Cg3ⁱ = 3.5864 (11) Å and Cg2···Cg3ⁱ_perp = 3.383 Å and α = 1.29° [symmetry code: (i) 1 - x, -y, 1 - z; Cg1, Cg2 and Cg3 are the centroids of C1—C5/N3 ring, C8—C12/N4 ring and C4—C9 ring, respectively; Cgi···Cgj_perp is the perpendicular distance from ring Cgi to ring Cgjⁱ; α is the dihedral angle between ring plane Cgi and ring plane Cgjⁱ].

Related literature top

For related structures, see: Liu et al. (2008); Zhang et al. (2008).

Experimental top

Powdered 2,9-Bis((pyridin-4-yl)methoxy)-1,10-phenanthroline (0.1025 g, 0.260 mmol) was dissolved in 15 ml methanol and yellow single crystals were obtained after the filtrate had been allowed to stand at room temperature for four weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2,9-Bis(4-pyridylmethoxy)-1,10-phenanthroline top

Crystal data top

C₂₄H₁₈N₄O₂	F(000) = 824
M_r = 394.42	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2776 reflections
a = 12.701 (2) Å	θ = 2.5–25.2°
b = 16.418 (3) Å	µ = 0.09 mm⁻¹
c = 9.7443 (16) Å	T = 298 K
β = 107.535 (2)°	Block, yellow
V = 1937.5 (6) Å³	0.51 × 0.40 × 0.38 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3530 independent reflections
Radiation source: fine-focus sealed tube	2603 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→11
T_min = 0.956, T_max = 0.967	k = −14→19
9860 measured reflections	l = −10→11

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0569P)² + 0.0745P] where P = (F_o² + 2F_c²)/3
3530 reflections	(Δ/σ)_max = 0.002
271 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₄H₁₈N₄O₂	V = 1937.5 (6) Å³
M_r = 394.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.701 (2) Å	µ = 0.09 mm⁻¹
b = 16.418 (3) Å	T = 298 K
c = 9.7443 (16) Å	0.51 × 0.40 × 0.38 mm
β = 107.535 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3530 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2603 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.967	R_int = 0.028
9860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
3530 reflections	Δρ_min = −0.16 e Å⁻³
271 parameters

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	U_iso*/U_eq
C1	0.50194 (13)	0.23897 (10)	0.53260 (16)	0.0523 (4)
C2	0.61170 (14)	0.25413 (11)	0.53679 (18)	0.0622 (5)
H2	0.6488	0.3003	0.5819	0.075*
C3	0.66137 (14)	0.19987 (12)	0.47360 (18)	0.0626 (5)
H3	0.7339	0.2085	0.4743	0.075*
C4	0.60421 (12)	0.12976 (10)	0.40609 (16)	0.0524 (4)
C5	0.49508 (11)	0.12005 (9)	0.40882 (14)	0.0449 (4)
C6	0.65165 (13)	0.07031 (12)	0.33719 (18)	0.0643 (5)
H6	0.7239	0.0769	0.3353	0.077*
C7	0.59392 (14)	0.00485 (12)	0.27477 (19)	0.0646 (5)
H7	0.6268	−0.0333	0.2301	0.078*
C8	0.43337 (11)	0.04990 (9)	0.34246 (15)	0.0441 (4)
C9	0.48333 (12)	−0.00739 (10)	0.27554 (16)	0.0516 (4)
C10	0.42012 (14)	−0.07576 (11)	0.21217 (17)	0.0600 (4)
H10	0.4501	−0.1146	0.1653	0.072*
C11	0.31631 (14)	−0.08512 (10)	0.21916 (17)	0.0579 (4)
H11	0.2737	−0.1300	0.1780	0.069*
C12	0.27507 (12)	−0.02471 (10)	0.29082 (16)	0.0486 (4)
C13	0.12405 (13)	0.01882 (12)	0.37343 (18)	0.0623 (5)
H13A	0.1829	0.0488	0.4413	0.075*
H13B	0.0830	−0.0100	0.4276	0.075*
C14	0.04897 (11)	0.07741 (10)	0.27374 (18)	0.0542 (4)
C15	0.03967 (13)	0.08218 (11)	0.12927 (18)	0.0610 (5)
H15	0.0832	0.0492	0.0906	0.073*
C16	−0.03412 (15)	0.13578 (12)	0.0426 (2)	0.0752 (5)
H16	−0.0389	0.1373	−0.0545	0.090*
C17	−0.01738 (13)	0.12956 (12)	0.3232 (2)	0.0675 (5)
H17	−0.0141	0.1296	0.4199	0.081*
C18	−0.08782 (15)	0.18100 (14)	0.2280 (3)	0.0829 (6)
H18	−0.1313	0.2155	0.2639	0.100*
C19	0.26496 (12)	0.31914 (10)	0.46362 (16)	0.0526 (4)
C20	0.13577 (17)	0.31235 (18)	0.2316 (2)	0.0918 (7)
H20	0.0968	0.2803	0.1542	0.110*
C21	0.20466 (15)	0.27345 (13)	0.34918 (19)	0.0721 (5)
H21	0.2103	0.2170	0.3512	0.087*
C22	0.17931 (16)	0.43588 (14)	0.3319 (2)	0.0781 (6)
H22	0.1710	0.4922	0.3281	0.094*
C23	0.25156 (14)	0.40236 (12)	0.4528 (2)	0.0636 (5)
H23	0.2914	0.4358	0.5275	0.076*
C24	0.34284 (14)	0.28164 (11)	0.59467 (17)	0.0622 (5)
H24A	0.3305	0.3051	0.6799	0.075*
H24B	0.3288	0.2236	0.5950	0.075*
N1	−0.09879 (13)	0.18537 (11)	0.0876 (2)	0.0860 (5)
N2	0.12073 (13)	0.39253 (15)	0.2202 (2)	0.0891 (6)
N3	0.44458 (9)	0.17568 (8)	0.47191 (12)	0.0472 (3)
N4	0.32756 (9)	0.04086 (7)	0.34768 (12)	0.0455 (3)
O1	0.17152 (8)	−0.03913 (7)	0.29945 (12)	0.0615 (3)
O2	0.45550 (9)	0.29496 (7)	0.59879 (12)	0.0660 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0513 (9)	0.0475 (10)	0.0472 (9)	−0.0005 (8)	−0.0017 (7)	0.0046 (8)
C2	0.0538 (10)	0.0537 (11)	0.0650 (11)	−0.0114 (8)	−0.0031 (8)	0.0087 (9)
C3	0.0434 (9)	0.0704 (12)	0.0662 (11)	−0.0102 (9)	0.0049 (8)	0.0173 (10)
C4	0.0418 (8)	0.0599 (11)	0.0521 (9)	−0.0008 (8)	0.0091 (7)	0.0135 (8)
C5	0.0419 (8)	0.0474 (9)	0.0402 (8)	0.0014 (7)	0.0043 (6)	0.0088 (7)
C6	0.0431 (9)	0.0840 (14)	0.0664 (11)	0.0034 (9)	0.0176 (8)	0.0102 (10)
C7	0.0553 (10)	0.0762 (13)	0.0658 (11)	0.0124 (10)	0.0234 (8)	−0.0016 (9)
C8	0.0400 (8)	0.0485 (9)	0.0401 (8)	0.0042 (7)	0.0064 (6)	0.0061 (7)
C9	0.0500 (9)	0.0556 (10)	0.0473 (9)	0.0088 (8)	0.0118 (7)	0.0023 (8)
C10	0.0637 (11)	0.0539 (11)	0.0575 (10)	0.0119 (8)	0.0109 (8)	−0.0084 (8)
C11	0.0591 (10)	0.0460 (10)	0.0590 (10)	0.0009 (8)	0.0032 (8)	−0.0056 (8)
C12	0.0421 (8)	0.0457 (9)	0.0513 (9)	−0.0006 (7)	0.0038 (7)	0.0036 (7)
C13	0.0459 (9)	0.0767 (12)	0.0654 (10)	−0.0077 (9)	0.0185 (8)	−0.0004 (9)
C14	0.0365 (8)	0.0619 (11)	0.0620 (10)	−0.0109 (7)	0.0114 (7)	−0.0110 (8)
C15	0.0481 (9)	0.0693 (12)	0.0631 (11)	0.0026 (8)	0.0130 (8)	−0.0089 (9)
C16	0.0634 (11)	0.0867 (15)	0.0662 (11)	0.0084 (11)	0.0054 (9)	−0.0062 (11)
C17	0.0475 (10)	0.0841 (14)	0.0718 (11)	−0.0079 (9)	0.0192 (9)	−0.0200 (10)
C18	0.0513 (11)	0.0878 (16)	0.1067 (18)	0.0102 (10)	0.0193 (11)	−0.0274 (13)
C19	0.0510 (9)	0.0587 (11)	0.0521 (9)	−0.0031 (8)	0.0216 (7)	−0.0066 (8)
C20	0.0708 (14)	0.122 (2)	0.0703 (13)	−0.0159 (13)	0.0028 (10)	−0.0075 (14)
C21	0.0717 (12)	0.0748 (13)	0.0633 (11)	−0.0110 (10)	0.0107 (9)	−0.0086 (10)
C22	0.0615 (12)	0.0805 (14)	0.1001 (16)	0.0159 (11)	0.0363 (12)	0.0180 (13)
C23	0.0602 (10)	0.0630 (12)	0.0709 (11)	0.0037 (9)	0.0246 (9)	−0.0052 (9)
C24	0.0737 (12)	0.0593 (11)	0.0532 (10)	−0.0022 (9)	0.0184 (8)	−0.0102 (8)
N1	0.0628 (10)	0.0889 (13)	0.0937 (13)	0.0183 (9)	0.0047 (9)	−0.0108 (10)
N2	0.0573 (10)	0.1221 (17)	0.0853 (12)	0.0093 (11)	0.0178 (9)	0.0238 (13)
N3	0.0450 (7)	0.0455 (8)	0.0446 (7)	−0.0008 (6)	0.0038 (5)	0.0012 (6)
N4	0.0408 (7)	0.0447 (8)	0.0469 (7)	0.0008 (6)	0.0070 (5)	0.0016 (6)
O1	0.0450 (6)	0.0579 (7)	0.0769 (8)	−0.0079 (5)	0.0111 (5)	−0.0047 (6)
O2	0.0624 (8)	0.0551 (7)	0.0686 (7)	−0.0029 (6)	0.0017 (6)	−0.0150 (6)

Geometric parameters (Å, º) top

C1—N3	1.3041 (19)	C13—H13A	0.9700
C1—O2	1.3558 (19)	C13—H13B	0.9700
C1—C2	1.405 (2)	C14—C15	1.379 (2)
C2—C3	1.343 (2)	C14—C17	1.386 (2)
C2—H2	0.9300	C15—C16	1.374 (2)
C3—C4	1.413 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—N1	1.322 (2)
C4—C5	1.403 (2)	C16—H16	0.9300
C4—C6	1.418 (2)	C17—C18	1.369 (3)
C5—N3	1.3641 (19)	C17—H17	0.9300
C5—C8	1.433 (2)	C18—N1	1.335 (3)
C6—C7	1.339 (2)	C18—H18	0.9300
C6—H6	0.9300	C19—C21	1.370 (2)
C7—C9	1.421 (2)	C19—C23	1.377 (2)
C7—H7	0.9300	C19—C24	1.492 (2)
C8—N4	1.3681 (18)	C20—N2	1.330 (3)
C8—C9	1.401 (2)	C20—C21	1.372 (3)
C9—C10	1.410 (2)	C20—H20	0.9300
C10—C11	1.349 (2)	C21—H21	0.9300
C10—H10	0.9300	C22—N2	1.325 (3)
C11—C12	1.402 (2)	C22—C23	1.372 (3)
C11—H11	0.9300	C22—H22	0.9300
C12—N4	1.2992 (18)	C23—H23	0.9300
C12—O1	1.3636 (17)	C24—O2	1.436 (2)
C13—O1	1.432 (2)	C24—H24A	0.9700
C13—C14	1.490 (2)	C24—H24B	0.9700

N3—C1—O2	119.50 (14)	C15—C14—C17	116.50 (16)
N3—C1—C2	124.64 (16)	C15—C14—C13	122.91 (15)
O2—C1—C2	115.86 (15)	C17—C14—C13	120.58 (16)
C3—C2—C1	117.91 (16)	C16—C15—C14	119.77 (17)
C3—C2—H2	121.0	C16—C15—H15	120.1
C1—C2—H2	121.0	C14—C15—H15	120.1
C2—C3—C4	120.48 (15)	N1—C16—C15	124.57 (19)
C2—C3—H3	119.8	N1—C16—H16	117.7
C4—C3—H3	119.8	C15—C16—H16	117.7
C5—C4—C3	117.10 (15)	C18—C17—C14	119.14 (17)
C5—C4—C6	119.59 (15)	C18—C17—H17	120.4
C3—C4—C6	123.31 (15)	C14—C17—H17	120.4
N3—C5—C4	122.25 (14)	N1—C18—C17	124.95 (18)
N3—C5—C8	118.29 (12)	N1—C18—H18	117.5
C4—C5—C8	119.46 (14)	C17—C18—H18	117.5
C7—C6—C4	120.99 (15)	C21—C19—C23	117.07 (17)
C7—C6—H6	119.5	C21—C19—C24	122.29 (16)
C4—C6—H6	119.5	C23—C19—C24	120.63 (15)
C6—C7—C9	121.18 (16)	N2—C20—C21	124.7 (2)
C6—C7—H7	119.4	N2—C20—H20	117.6
C9—C7—H7	119.4	C21—C20—H20	117.6
N4—C8—C9	122.16 (14)	C19—C21—C20	119.0 (2)
N4—C8—C5	118.70 (13)	C19—C21—H21	120.5
C9—C8—C5	119.14 (13)	C20—C21—H21	120.5
C8—C9—C10	117.42 (14)	N2—C22—C23	123.7 (2)
C8—C9—C7	119.64 (15)	N2—C22—H22	118.2
C10—C9—C7	122.93 (15)	C23—C22—H22	118.2
C11—C10—C9	120.31 (15)	C22—C23—C19	119.93 (18)
C11—C10—H10	119.8	C22—C23—H23	120.0
C9—C10—H10	119.8	C19—C23—H23	120.0
C10—C11—C12	117.52 (15)	O2—C24—C19	111.04 (13)
C10—C11—H11	121.2	O2—C24—H24A	109.4
C12—C11—H11	121.2	C19—C24—H24A	109.4
N4—C12—O1	119.88 (14)	O2—C24—H24B	109.4
N4—C12—C11	125.30 (14)	C19—C24—H24B	109.4
O1—C12—C11	114.82 (14)	H24A—C24—H24B	108.0
O1—C13—C14	112.62 (14)	C16—N1—C18	115.06 (17)
O1—C13—H13A	109.1	C22—N2—C20	115.61 (18)
C14—C13—H13A	109.1	C1—N3—C5	117.62 (13)
O1—C13—H13B	109.1	C12—N4—C8	117.24 (13)
C14—C13—H13B	109.1	C12—O1—C13	118.41 (12)
H13A—C13—H13B	107.8	C1—O2—C24	117.13 (12)

N3—C1—C2—C3	0.2 (2)	C14—C15—C16—N1	0.5 (3)
O2—C1—C2—C3	179.44 (14)	C15—C14—C17—C18	0.8 (2)
C1—C2—C3—C4	−0.3 (2)	C13—C14—C17—C18	−178.10 (16)
C2—C3—C4—C5	−0.1 (2)	C14—C17—C18—N1	0.2 (3)
C2—C3—C4—C6	179.82 (15)	C23—C19—C21—C20	0.4 (2)
C3—C4—C5—N3	0.7 (2)	C24—C19—C21—C20	−179.17 (16)
C6—C4—C5—N3	−179.19 (13)	N2—C20—C21—C19	−1.4 (3)
C3—C4—C5—C8	−179.77 (13)	N2—C22—C23—C19	−1.0 (3)
C6—C4—C5—C8	0.3 (2)	C21—C19—C23—C22	0.7 (2)
C5—C4—C6—C7	−0.1 (2)	C24—C19—C23—C22	−179.74 (15)
C3—C4—C6—C7	179.96 (15)	C21—C19—C24—O2	106.35 (17)
C4—C6—C7—C9	−0.1 (3)	C23—C19—C24—O2	−73.16 (19)
N3—C5—C8—N4	−1.30 (19)	C15—C16—N1—C18	0.5 (3)
C4—C5—C8—N4	179.19 (12)	C17—C18—N1—C16	−0.8 (3)
N3—C5—C8—C9	179.21 (12)	C23—C22—N2—C20	0.1 (3)
C4—C5—C8—C9	−0.3 (2)	C21—C20—N2—C22	1.1 (3)
N4—C8—C9—C10	0.2 (2)	O2—C1—N3—C5	−178.81 (12)
C5—C8—C9—C10	179.67 (13)	C2—C1—N3—C5	0.4 (2)
N4—C8—C9—C7	−179.36 (13)	C4—C5—N3—C1	−0.9 (2)
C5—C8—C9—C7	0.1 (2)	C8—C5—N3—C1	179.62 (12)
C6—C7—C9—C8	0.1 (2)	O1—C12—N4—C8	176.56 (12)
C6—C7—C9—C10	−179.45 (16)	C11—C12—N4—C8	−2.9 (2)
C8—C9—C10—C11	−1.1 (2)	C9—C8—N4—C12	1.7 (2)
C7—C9—C10—C11	178.44 (15)	C5—C8—N4—C12	−177.73 (12)
C9—C10—C11—C12	0.1 (2)	N4—C12—O1—C13	−0.8 (2)
C10—C11—C12—N4	2.1 (2)	C11—C12—O1—C13	178.80 (13)
C10—C11—C12—O1	−177.47 (13)	C14—C13—O1—C12	97.39 (15)
O1—C13—C14—C15	−8.9 (2)	N3—C1—O2—C24	−1.5 (2)
O1—C13—C14—C17	169.93 (14)	C2—C1—O2—C24	179.22 (13)
C17—C14—C15—C16	−1.1 (2)	C19—C24—O2—C1	−88.63 (16)
C13—C14—C15—C16	177.76 (15)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈N₄O₂
M_r	394.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.701 (2), 16.418 (3), 9.7443 (16)
β (°)	107.535 (2)
V (Å³)	1937.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.51 × 0.40 × 0.38

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	9860, 3530, 2603
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.03
No. of reflections	3530
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Project of Scientific Studies Development of Shandong Provincial Education Department (grant No. J08LC51) and the Natural Science Foundation of Shandong Province of China (grant No. Y2007B26).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S. G. & Hou, C. (2008). Acta Cryst. E64, o1450. Web of Science CSD CrossRef IUCr Journals Google Scholar