N,N′-Bis(2-furylmethyl­ene)-1,1′-binaphthyl-2,2′-diamine

ElMkacher, N.B.M.; Rzaigui, M.; Bouachir, F.

doi:10.1107/S1600536807065750

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o271

https://doi.org/10.1107/S1600536807065750

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N,N′-Bis(2-furylmethylene)-1,1′-binaphthyl-2,2′-diamine

Najoua Belhaj Mbarek ElMkacher,^a ^* Mohamed Rzaigui ^b and Faouzi Bouachir ^a

^aDépartement de Chimie, Faculté des Sciences, 5019, Monastir, Tunisia, and ^bDépartement de Chimie, Faculté des Sciences, 7021, Bizerte, Tunisia
^*Correspondence e-mail: najouahaj@yahoo.fr

(Received 22 November 2007; accepted 5 December 2007; online 12 December 2007)

In the title compound, C₃₀H₂₀N₂O₂, the orientation of the furyl group may induce a variety of coordination modes with this ligand. The dihedral angle between the two naphthyl rings is 79.25 (7)°. The furyl groups make dihedral angles of 62.0 (1) and 16.3 (2)° with the attached naphthyl groups. The dihedral angle between the two furyl rings is 49.3 (2)°.

Related literature

For related literature see: Chen et al. (1995 ); Dang et al. (1971 ); Grubbs et al. (1977 ); Horner et al. (1968 ); Miyashita et al. (1980 ); Nishinaga et al. (1988 ); Pertici et al. (1996 ); Rosini et al. (1992 ); Suda et al. (1983 ); Spassky et al. (1996 ); Suga et al. (2003 ).

Experimental

Crystal data

C₃₀H₂₀N₂O₂
M_r = 440.48
Monoclinic, P 2₁ /n
a = 8.2433 (2) Å
b = 15.5046 (3) Å
c = 17.7432 (3) Å
β = 91.309 (3)°
V = 2267.15 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.23 × 0.15 × 0.12 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction: none
4133 measured reflections
4016 independent reflections
1600 reflections with I > 2σ(I)
R_int = 0.028
2 standard reflections frequency: 120 min intensity decay: −1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.146
S = 0.97
4016 reflections
331 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807065750/hj2001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065750/hj2001Isup2.hkl

checkCIF report

Comment top

The importance of axially chiral ligands in catalytic asymmetric reactions is well known in the development of stereoselective hydrogenation of olefins.The low enantiomeric excess induced by the first chiral monodentate phosphane ligands (Horner et al., 1968) was soon enhanced by chelating bisphosphanes (Dang et al., 1971). Axially chiral ligands were first reported in a hydrogenation reaction in 1977 and have gained ground ever since (Grubbs et al., 1977).In addition to the biaryl backbone bisphosphanes (2,2'-bis (diphenylphosphino)-1,1'-binaphthyl) (Miyashita et al., 1980), derivatives of the corresponding diamines (biphenyldiamine and binaphthyldiamine) have performed successfully in many asymmetric catalytic reactions (Rosini et al., 1992). These include stereoselective polymerizations of methacrylate (Suda et al., 1983) and lactate (Spassky et al., 1996) and numerous enantioselective modifications of olefins such as epoxidation (Nishinaga et al., 1988), aziridination (Suga et al., 2003), cyclopropanation (Chen et al., 1995) and hydrogenation (Pertici et al., 1996). With a structurally rigid binaphthyl ligand backbone, the configuration of the ligand is fixed and its axial chirality can efficiently be transmitted to the active site catalyst. We report here the crystal structure of (I) which was synthesized via condensation of the axially chiral binaphthyldiamine with the 2-furfuraldehyde. The centrosymmetric crystal structure shows that there is racemization which may occur during the reaction of condensation. The molecule of (I) has two imine groups with bond distances N1—C1 1.264 (5) Å and N2—C26 1.268 (4) Å. Each imine group is bound to a furfuryl group such that C1—C2 1.445 (5) and C26—C27 1.431 (5) Å. Variation between N—C (N1—C1 and N2—C26) and C—C (C1—C2 and C26—C27) bonds are statistically insignificant. The naphthyl rings make a dihedral angle of 79.25 (7) ° with one another. The furyl group C2C3C4C5O1 makes a dihedral angle of 62.0 (1) ° with its attached binaphthyl group. The other furyl makes a dihedral angle of 16.3 (2) ° with its binaphthyl group. The furyl groups make a dihedral angle of 49.3 (2) ° with one another.

Related literature top

For related literature see: Chen et al. (1995); Dang et al. (1971); Grubbs et al. (1977); Horner et al. (1968); Miyashita et al. (1980); Nishinaga et al. (1988); Pertici et al. (1996); Rosini et al. (1992); Suda et al. (1983); Spassky et al. (1996); Suga et al. (2003)

Experimental top

The title compound was obtained as follows: to a stirred solution of the 2-furfuraldehyde (0.067 g, 0.703 mmol) in absolute ethanol (10 ml) was added the enantiomerically pure 2,2'-diamino-1,1'-binaphthyl (0.1 g,0.35 mmol). The resulting suspension was heated at reflux for 24 h. The pure yellow ligand was obtained after crystallization in absolute ethanol.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted.

N,N'-Bis(2-furylmethylene)-1,1'-binaphthyl-2,2'-diamine top

Crystal data top

C₃₀H₂₀N₂O₂	F(000) = 920
M_r = 440.48	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.2433 (2) Å	θ = 9.9–11.0°
b = 15.5046 (3) Å	µ = 0.08 mm⁻¹
c = 17.7432 (3) Å	T = 293 K
β = 91.309 (3)°	Prism, yellow
V = 2267.15 (8) Å³	0.23 × 0.15 × 0.12 mm
Z = 4

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.028
Radiation source: fine-focus sealed tube	θ_max = 25°, θ_min = 2.3°
Graphite monochromator	h = −10→10
non–profiled ω scans	k = 0→18
4133 measured reflections	l = 0→21
4016 independent reflections	2 standard reflections every 120 min
1600 reflections with I > 2σ(I)	intensity decay: −1%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0464P)²] where P = (F_o² + 2F_c²)/3
4016 reflections	(Δ/σ)_max < 0.001
331 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₃₀H₂₀N₂O₂	V = 2267.15 (8) Å³
M_r = 440.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2433 (2) Å	µ = 0.08 mm⁻¹
b = 15.5046 (3) Å	T = 293 K
c = 17.7432 (3) Å	0.23 × 0.15 × 0.12 mm
β = 91.309 (3)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.028
4133 measured reflections	2 standard reflections every 120 min
4016 independent reflections	intensity decay: −1%
1600 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.17 e Å⁻³
4016 reflections	Δρ_min = −0.18 e Å⁻³
331 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
O1	0.9295 (4)	0.7193 (2)	−0.20480 (18)	0.0883 (10)
O2	0.4942 (3)	0.94701 (19)	−0.06519 (15)	0.0583 (7)
N1	1.0080 (4)	0.7947 (2)	−0.0674 (2)	0.0614 (10)
N2	0.6396 (3)	0.7971 (2)	−0.00840 (18)	0.0503 (9)
C1	1.0368 (5)	0.8348 (3)	−0.1278 (3)	0.0640 (13)
H1	1.086 (4)	0.900 (2)	−0.128 (2)	0.077*
C2	1.0049 (5)	0.7968 (3)	−0.2010 (3)	0.0572 (11)
C3	1.0277 (6)	0.8265 (3)	−0.2713 (3)	0.0731 (15)
H3	1.068 (5)	0.882 (3)	−0.281 (2)	0.088*
C4	0.9647 (6)	0.7628 (4)	−0.3211 (3)	0.0820 (16)
H4	0.959 (5)	0.767 (3)	−0.373 (2)	0.098*
C5	0.9084 (6)	0.7002 (4)	−0.2798 (3)	0.0917 (17)
H5	0.863 (5)	0.635 (3)	−0.284 (2)	0.110*
C6	1.0290 (4)	0.8361 (2)	0.0035 (2)	0.0510 (11)
C7	1.1278 (5)	0.9100 (3)	0.0148 (3)	0.0685 (13)
H7	1.1838	0.9331	−0.0254	0.082*
C8	1.1413 (5)	0.9477 (3)	0.0842 (3)	0.0670 (12)
H8	1.2056	0.9965	0.0908	0.080*
C9	1.0583 (5)	0.9130 (3)	0.1462 (3)	0.0530 (11)
C10	1.0706 (5)	0.9520 (3)	0.2183 (3)	0.0677 (13)
H10	1.1338	1.0012	0.2252	0.081*
C11	0.9906 (6)	0.9180 (3)	0.2772 (3)	0.0758 (14)
H11	1.0008	0.9432	0.3247	0.091*
C12	0.8931 (5)	0.8453 (3)	0.2669 (2)	0.0688 (13)
H12	0.8363	0.8233	0.3073	0.083*
C13	0.8799 (5)	0.8062 (3)	0.1986 (2)	0.0568 (11)
H13	0.8159	0.7571	0.1930	0.068*
C14	0.9628 (4)	0.8395 (2)	0.1355 (2)	0.0461 (10)
C15	0.9504 (4)	0.7992 (2)	0.0629 (2)	0.0440 (10)
C16	0.8575 (4)	0.7176 (2)	0.05238 (19)	0.0417 (9)
C17	0.7078 (4)	0.7177 (3)	0.0167 (2)	0.0475 (10)
C18	0.6187 (5)	0.6405 (3)	0.0082 (2)	0.0637 (12)
H18	0.5171	0.6412	−0.0156	0.076*
C19	0.6821 (5)	0.5652 (3)	0.0349 (2)	0.0703 (13)
H19	0.6199	0.5152	0.0309	0.085*
C20	0.8384 (5)	0.5600 (3)	0.0684 (2)	0.0585 (11)
C21	0.9119 (7)	0.4816 (3)	0.0909 (2)	0.0769 (14)
H21	0.8541	0.4303	0.0859	0.092*
C22	1.0659 (7)	0.4800 (3)	0.1198 (3)	0.0835 (16)
H22	1.1131	0.4280	0.1346	0.100*
C23	1.1524 (6)	0.5562 (3)	0.1273 (2)	0.0754 (14)
H23	1.2581	0.5548	0.1467	0.090*
C24	1.0856 (5)	0.6329 (3)	0.1068 (2)	0.0610 (12)
H24	1.1461	0.6831	0.1129	0.073*
C25	0.9267 (5)	0.6381 (2)	0.0765 (2)	0.0472 (10)
C26	0.5987 (5)	0.8037 (3)	−0.0775 (2)	0.0540 (11)
H26	0.619 (4)	0.759 (2)	−0.1130 (19)	0.065*
C27	0.5253 (5)	0.8786 (3)	−0.1108 (2)	0.0525 (11)
C28	0.4798 (7)	0.8988 (3)	−0.1816 (3)	0.0823 (16)
H28	0.500 (5)	0.863 (3)	−0.223 (2)	0.099*
C29	0.4167 (6)	0.9820 (4)	−0.1811 (3)	0.0842 (17)
H29	0.370 (5)	1.015 (3)	−0.221 (2)	0.102*
C30	0.4264 (6)	1.0095 (3)	−0.1108 (3)	0.0713 (14)
H30	0.399 (5)	1.066 (2)	−0.082 (2)	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C15	0.039 (2)	0.042 (2)	0.050 (3)	−0.0070 (19)	−0.009 (2)	0.006 (2)
O2	0.0567 (17)	0.0603 (19)	0.0581 (17)	0.0050 (16)	0.0043 (14)	0.0058 (17)
C14	0.037 (2)	0.044 (3)	0.056 (3)	−0.004 (2)	−0.013 (2)	0.004 (2)
N2	0.0426 (19)	0.057 (2)	0.051 (2)	−0.0002 (17)	−0.0076 (17)	−0.0008 (18)
C16	0.043 (2)	0.041 (2)	0.041 (2)	−0.005 (2)	−0.0010 (18)	0.0004 (19)
C6	0.048 (3)	0.047 (3)	0.058 (3)	−0.004 (2)	−0.002 (2)	0.003 (2)
C17	0.046 (2)	0.047 (3)	0.049 (3)	−0.004 (2)	−0.006 (2)	0.000 (2)
N1	0.065 (2)	0.065 (2)	0.055 (2)	−0.013 (2)	0.0055 (19)	0.011 (2)
O1	0.104 (3)	0.089 (3)	0.073 (2)	−0.031 (2)	0.0025 (19)	0.001 (2)
C9	0.045 (3)	0.045 (3)	0.068 (3)	−0.004 (2)	−0.014 (2)	−0.002 (2)
C18	0.058 (3)	0.053 (3)	0.079 (3)	−0.011 (3)	−0.014 (2)	−0.009 (2)
C27	0.055 (3)	0.055 (3)	0.047 (3)	−0.008 (2)	−0.009 (2)	0.007 (2)
C12	0.080 (3)	0.073 (3)	0.053 (3)	−0.006 (3)	−0.005 (2)	−0.010 (3)
C25	0.055 (3)	0.043 (3)	0.044 (2)	−0.006 (2)	−0.001 (2)	0.000 (2)
C2	0.056 (3)	0.050 (3)	0.066 (3)	−0.002 (2)	0.009 (2)	0.007 (3)
C26	0.049 (3)	0.059 (3)	0.053 (3)	−0.005 (2)	−0.003 (2)	−0.009 (2)
C20	0.068 (3)	0.053 (3)	0.055 (3)	−0.009 (3)	0.001 (2)	0.002 (2)
C8	0.051 (3)	0.056 (3)	0.094 (4)	−0.015 (2)	−0.007 (3)	−0.008 (3)
C13	0.062 (3)	0.051 (3)	0.057 (3)	−0.008 (2)	−0.007 (2)	0.000 (2)
C24	0.068 (3)	0.055 (3)	0.059 (3)	0.006 (2)	−0.016 (2)	0.005 (2)
C1	0.071 (3)	0.055 (3)	0.066 (3)	0.001 (3)	0.010 (3)	−0.005 (3)
C7	0.059 (3)	0.063 (3)	0.084 (4)	−0.021 (2)	0.007 (3)	0.005 (3)
C30	0.066 (3)	0.067 (3)	0.081 (4)	0.005 (3)	0.009 (3)	0.024 (3)
C11	0.089 (4)	0.072 (4)	0.065 (3)	−0.002 (3)	−0.019 (3)	−0.015 (3)
C10	0.067 (3)	0.051 (3)	0.084 (3)	−0.009 (2)	−0.024 (3)	−0.011 (3)
C21	0.117 (4)	0.049 (3)	0.065 (3)	−0.003 (3)	0.004 (3)	0.009 (2)
C23	0.085 (3)	0.064 (3)	0.076 (3)	0.010 (3)	−0.017 (3)	0.008 (3)
C19	0.079 (3)	0.048 (3)	0.084 (3)	−0.022 (3)	−0.002 (3)	−0.003 (3)
C29	0.089 (4)	0.081 (4)	0.082 (4)	−0.009 (3)	−0.025 (3)	0.026 (3)
C5	0.095 (4)	0.110 (5)	0.071 (4)	−0.016 (4)	−0.001 (3)	−0.014 (4)
C4	0.073 (3)	0.115 (5)	0.058 (3)	0.016 (3)	0.010 (3)	0.003 (4)
C3	0.092 (4)	0.062 (3)	0.067 (3)	0.005 (3)	0.023 (3)	0.010 (3)
C28	0.112 (4)	0.071 (4)	0.062 (4)	0.000 (3)	−0.013 (3)	0.001 (3)
C22	0.115 (5)	0.067 (4)	0.068 (3)	0.028 (4)	−0.003 (3)	0.017 (3)

Geometric parameters (Å, º) top

C15—C6	1.374 (5)	C26—H26	0.95 (3)
C15—C14	1.434 (5)	C20—C19	1.409 (5)
C15—C16	1.488 (5)	C20—C21	1.413 (6)
O2—C27	1.363 (4)	C8—C7	1.366 (5)
O2—C30	1.373 (5)	C8—H8	0.9300
C14—C9	1.395 (5)	C13—H13	0.9300
C14—C13	1.421 (5)	C24—C23	1.357 (5)
N2—C26	1.268 (4)	C24—H24	0.9300
N2—C17	1.421 (4)	C1—H1	1.09 (4)
C16—C17	1.374 (4)	C7—H7	0.9300
C16—C25	1.420 (5)	C30—C29	1.320 (6)
C6—C7	1.418 (5)	C30—H30	1.04 (4)
C6—N1	1.420 (4)	C11—C10	1.356 (6)
C17—C18	1.410 (5)	C11—H11	0.9300
N1—C1	1.264 (5)	C10—H10	0.9300
O1—C2	1.354 (5)	C21—C22	1.359 (6)
O1—C5	1.370 (5)	C21—H21	0.9300
C9—C8	1.415 (5)	C23—C22	1.385 (6)
C9—C10	1.416 (5)	C23—H23	0.9300
C18—C19	1.361 (5)	C19—H19	0.9300
C18—H18	0.9300	C29—C28	1.392 (6)
C27—C28	1.339 (5)	C29—H29	0.95 (4)
C27—C26	1.431 (5)	C5—C4	1.308 (7)
C12—C13	1.357 (5)	C5—H5	1.08 (4)
C12—C11	1.394 (5)	C4—C3	1.416 (7)
C12—H12	0.9300	C4—H4	0.92 (4)
C25—C24	1.407 (5)	C3—H3	0.94 (4)
C25—C20	1.418 (5)	C28—H28	0.93 (4)
C2—C3	1.348 (5)	C22—H22	0.9300
C2—C1	1.445 (5)

C6—C15—C14	118.8 (4)	C12—C13—H13	119.6
C6—C15—C16	120.6 (3)	C14—C13—H13	119.6
C14—C15—C16	120.6 (4)	C23—C24—C25	121.4 (4)
C27—O2—C30	106.2 (3)	C23—C24—H24	119.3
C9—C14—C13	118.0 (4)	C25—C24—H24	119.3
C9—C14—C15	120.4 (4)	N1—C1—C2	121.8 (4)
C13—C14—C15	121.6 (4)	N1—C1—H1	122 (2)
C26—N2—C17	117.9 (3)	C2—C1—H1	115.8 (19)
C17—C16—C25	119.3 (3)	C8—C7—C6	120.5 (4)
C17—C16—C15	120.8 (3)	C8—C7—H7	119.8
C25—C16—C15	119.9 (3)	C6—C7—H7	119.8
C15—C6—C7	120.6 (4)	C29—C30—O2	110.1 (5)
C15—C6—N1	116.2 (4)	C29—C30—H30	136 (2)
C7—C6—N1	123.2 (4)	O2—C30—H30	114 (2)
C16—C17—C18	120.6 (4)	C10—C11—C12	120.2 (4)
C16—C17—N2	119.3 (3)	C10—C11—H11	119.9
C18—C17—N2	120.0 (3)	C12—C11—H11	119.9
C1—N1—C6	120.5 (4)	C11—C10—C9	120.2 (4)
C2—O1—C5	106.8 (4)	C11—C10—H10	119.9
C14—C9—C8	119.1 (4)	C9—C10—H10	119.9
C14—C9—C10	120.1 (4)	C22—C21—C20	120.9 (5)
C8—C9—C10	120.9 (4)	C22—C21—H21	119.6
C19—C18—C17	119.8 (4)	C20—C21—H21	119.6
C19—C18—H18	120.1	C24—C23—C22	121.2 (4)
C17—C18—H18	120.1	C24—C23—H23	119.4
C28—C27—O2	108.8 (4)	C22—C23—H23	119.4
C28—C27—C26	133.2 (5)	C18—C19—C20	122.4 (4)
O2—C27—C26	118.0 (4)	C18—C19—H19	118.8
C13—C12—C11	120.9 (4)	C20—C19—H19	118.8
C13—C12—H12	119.6	C30—C29—C28	106.9 (5)
C11—C12—H12	119.6	C30—C29—H29	123 (3)
C24—C25—C20	117.4 (4)	C28—C29—H29	130 (3)
C24—C25—C16	121.9 (4)	C4—C5—O1	110.2 (5)
C20—C25—C16	120.6 (4)	C4—C5—H5	142 (2)
C3—C2—O1	109.3 (4)	O1—C5—H5	107 (2)
C3—C2—C1	131.9 (5)	C5—C4—C3	107.3 (5)
O1—C2—C1	118.7 (4)	C5—C4—H4	127 (3)
N2—C26—C27	124.5 (4)	C3—C4—H4	126 (3)
N2—C26—H26	122 (2)	C2—C3—C4	106.4 (4)
C27—C26—H26	113 (2)	C2—C3—H3	123 (3)
C19—C20—C21	123.4 (4)	C4—C3—H3	130 (3)
C19—C20—C25	117.2 (4)	C27—C28—C29	107.9 (5)
C21—C20—C25	119.4 (4)	C27—C28—H28	123 (3)
C7—C8—C9	120.5 (4)	C29—C28—H28	129 (3)
C7—C8—H8	119.7	C21—C22—C23	119.7 (5)
C9—C8—H8	119.7	C21—C22—H22	120.2
C12—C13—C14	120.7 (4)	C23—C22—H22	120.2

C6—C15—C14—C9	−2.4 (5)	C16—C25—C20—C19	0.8 (5)
C16—C15—C14—C9	176.0 (3)	C24—C25—C20—C21	0.2 (5)
C6—C15—C14—C13	177.8 (3)	C16—C25—C20—C21	178.3 (4)
C16—C15—C14—C13	−3.8 (5)	C14—C9—C8—C7	0.3 (6)
C6—C15—C16—C17	−76.0 (5)	C10—C9—C8—C7	−179.5 (4)
C14—C15—C16—C17	105.6 (4)	C11—C12—C13—C14	−1.2 (6)
C6—C15—C16—C25	101.2 (4)	C9—C14—C13—C12	0.3 (5)
C14—C15—C16—C25	−77.2 (4)	C15—C14—C13—C12	−179.9 (4)
C14—C15—C6—C7	3.3 (5)	C20—C25—C24—C23	0.3 (6)
C16—C15—C6—C7	−175.1 (4)	C16—C25—C24—C23	−177.8 (4)
C14—C15—C6—N1	−178.1 (3)	C6—N1—C1—C2	−175.2 (4)
C16—C15—C6—N1	3.5 (5)	C3—C2—C1—N1	−179.0 (5)
C25—C16—C17—C18	4.0 (5)	O1—C2—C1—N1	5.7 (7)
C15—C16—C17—C18	−178.7 (4)	C9—C8—C7—C6	0.6 (6)
C25—C16—C17—N2	−179.1 (3)	C15—C6—C7—C8	−2.5 (6)
C15—C16—C17—N2	−1.8 (5)	N1—C6—C7—C8	179.1 (4)
C26—N2—C17—C16	124.2 (4)	C27—O2—C30—C29	−0.4 (5)
C26—N2—C17—C18	−58.9 (5)	C13—C12—C11—C10	1.7 (7)
C15—C6—N1—C1	160.8 (4)	C12—C11—C10—C9	−1.3 (6)
C7—C6—N1—C1	−20.7 (6)	C14—C9—C10—C11	0.4 (6)
C13—C14—C9—C8	−179.6 (3)	C8—C9—C10—C11	−179.9 (4)
C15—C14—C9—C8	0.6 (5)	C19—C20—C21—C22	177.0 (4)
C13—C14—C9—C10	0.1 (5)	C25—C20—C21—C22	−0.3 (6)
C15—C14—C9—C10	−179.6 (3)	C25—C24—C23—C22	−0.7 (7)
C16—C17—C18—C19	−0.6 (6)	C17—C18—C19—C20	−2.8 (6)
N2—C17—C18—C19	−177.5 (4)	C21—C20—C19—C18	−174.6 (4)
C30—O2—C27—C28	0.6 (5)	C25—C20—C19—C18	2.7 (6)
C30—O2—C27—C26	179.4 (3)	O2—C30—C29—C28	0.1 (6)
C17—C16—C25—C24	173.9 (3)	C2—O1—C5—C4	−1.1 (6)
C15—C16—C25—C24	−3.4 (5)	O1—C5—C4—C3	0.5 (7)
C17—C16—C25—C20	−4.1 (5)	O1—C2—C3—C4	−0.9 (5)
C15—C16—C25—C20	178.6 (3)	C1—C2—C3—C4	−176.6 (5)
C5—O1—C2—C3	1.2 (5)	C5—C4—C3—C2	0.2 (6)
C5—O1—C2—C1	177.5 (4)	O2—C27—C28—C29	−0.5 (6)
C17—N2—C26—C27	178.6 (3)	C26—C27—C28—C29	−179.1 (4)
C28—C27—C26—N2	177.2 (5)	C30—C29—C28—C27	0.2 (6)
O2—C27—C26—N2	−1.4 (6)	C20—C21—C22—C23	−0.1 (7)
C24—C25—C20—C19	−177.3 (4)	C24—C23—C22—C21	0.6 (7)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₀N₂O₂
M_r	440.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.2433 (2), 15.5046 (3), 17.7432 (3)
β (°)	91.309 (3)
V (Å³)	2267.15 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.15 × 0.12

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4133, 4016, 1600
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.146, 0.97
No. of reflections	4016
No. of parameters	331
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Selected geometric parameters (Å, º) top

N2—C26	1.268 (4)	C27—C26	1.431 (5)
N2—C17	1.421 (4)	C2—C1	1.445 (5)
C6—N1	1.420 (4)	C26—H26	0.95 (3)
N1—C1	1.264 (5)	C1—H1	1.09 (4)

C26—N2—C17	117.9 (3)	C18—C17—N2	120.0 (3)
C15—C6—N1	116.2 (4)	C1—N1—C6	120.5 (4)
C7—C6—N1	123.2 (4)	N2—C26—C27	124.5 (4)
C16—C17—N2	119.3 (3)	N1—C1—C2	121.8 (4)

C6—C15—C16—C17	−76.0 (5)	C6—C15—C16—C25	101.2 (4)

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