4-(1-Naphthoxy)­phthalo­nitrile

Karadayı, N.; Akdemir, N.; Agˇar, E.; Gümrükçüoǧlu, I.E.; Büyükgüngör, O.

doi:10.1107/S160053680301225X

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4-(1-Naphthoxy)phthalonitrile

N. Karadayi, N. Akdemir, E. Agar, I. E. Gümrükçüogglu and O. Büyükgüngör

The title compound, C₁₈H₁₀N₂O, crystallizes with two molecules in the asymmetric unit. The molecules are non-planar and the two independent molecules have different orientations. The dihedral angles between the least-squares planes of the naphthalene and the benzene ring in the independent molecules are 85.52 (3) and 73.40 (3)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301225X/na6242sup1.cif Contains datablocks nev2, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301225X/na6242Isup2.hkl Contains datablock I

CCDC reference: 217452

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.032
wR factor = 0.074
Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



DIFF_019  Alert A _diffrn_standards_number is missing
          Number of standards used in measurement.

DIFF_020  Alert A _diffrn_standards_interval_count and
          _diffrn_standards_interval_time are missing. Number of measurements
          between standards or time (min) between standards.


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.725

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5899

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C14A   -   C18A     =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C15A   -   C17A     =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C14B   -   C18B     =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C15B   -   C17B     =       1.43 Ang.


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 6 Alert Level C = Please check

Comment top

The 4-(1-naphthoxy)phthalonitrile, is a starting material in the synthesis of peripherally tetra-substituted phthalocyanines (Leznoff & Lever, 1996). Since their discovery earlier this century, phthalocyanines have been of great interest to chemists, physicists and industrial scientists. Phthalocyanines have continously been the subject of research due to their wide application fields. These include crystals, thin film fabrication including molecular epitaxic deposition and composites, liquid crystals and self-assembled materials. The fundamental optical and electronic properties of these materials are explained and their potential in nonlinear optics, optical data storage, electronic sensors, xerography, solar energy conversion, nuclear chemistry, molecular magnetism, electrochromic displays and heterogeneous catalysis is evaluated (McKeown et al., 1998).

Compound (I) contains two molecules in the asymmetric unit, designated A and B (Fig. 1). The triple-bond distances C17A≡N1A and C18A≡N2A, 1.136 (2) Å and 1.134 (2) Å, respectively, agree with the literature values (Allen et al., 1986; Öztürk et al., 2000). The bond angles around C17A and C18A agree with the triple-bond character of C17A≡N1A and C18A≡N2A. The C11A—O1A bond length is 1.3657 (17) Å, which is similar to the observed values in the literature 2-(3,4-dimethoxyphenoxy)benzoic acid (1.376 (2) Å; Gales et al., 2001). The bond lengths and angles for compound (I) are listed in Table 1. The two independent molecules have different orientations. The dihedral angles between the naphthalene and the phenyl ring are 85.52 (3)° for A and 73.40 (3)° for B.

Experimental top

The 1-naphthol (1.24 g, 7.6 mmol) was dissolved in dry DMF (40 ml) and 4-nitrophthalonitrile (1.32 g, 7.6 mmol) was added. After stirring for 30 min at room temperature dry fine-powdered potassium carbonate (3.00 g, 21.7 mmol) was added portionwise over 2 h with efficient stirring. The reaction was stirred for 24 h at room temperature and then poured into ice-water (150 g). The product filtered off and washed with (%10 w/w) NaOH solution and water until the filtrate was neutral. Recrystallization from ethanol gave a brown-cloused product. Yield 1.45 (70.4%). The single crystals were obtained in ethanol at room temperature via slow evaporation (m.p.:401–403 K); elemental analysis, calculated for C₁₈H₁₀N₂O: C 79.99, H 3.73, N 10.36%; found: C 79.97, H 3.76, N 10.40%. IR (ν_max/cm^-1): 3080–3025(Ar—CH), 2210(CN), 1622, 1590, 1555, 1500, 1472, 1452, 1416, 1380, 1276, 1208, 1190, 1052, 1084, 1064, 1032, 1008, 940, 880, 854, 828, 800, 780, 740, 716, 696, 656, 624, 612, 590, 568, 516. ¹H NMR (Acetone-d₆): 7.22–8.14 (m,10H). ¹³C NMR (Acetone-d₆): 109.71, 115.89, 116.31, 117.67, 118.93, 121.97, 122.38, 122.74, 126.91, 127.04, 127.39, 127.78, 127.93, 129.15, 136.26, 136.84, 150.57, 163.02.

Structure description top

Computing details top

Data collection: STOE X-AREA (Stoe & Cie, 2002); cell refinement: STOE X-AREA (Stoe & Cie, 2002); data reduction: STOE X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 1997).

Figures top

	Fig. 1. An ORTEPIII (Burnett & Johnson, 1996) drawing of the title compound (I) showing the atomic numbering scheme.
	Fig. 2. PLATON/PLUTON plot (Spek, 1997), viewed down the b axis, showing part of the stacking of molecules.

4-(1-Naphthoxy)phthalonitrile top

Crystal data top

C₁₈H₁₀N₂O	F(000) = 1120
M_r = 270.28	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15908 reflections
a = 17.7196 (13) Å	θ = 0.0–29.2°
b = 12.0092 (11) Å	µ = 0.08 mm⁻¹
c = 13.2800 (19) Å	T = 293 K
β = 97.976 (8)°	Plate, light brown
V = 2798.6 (5) Å³	0.50 × 0.38 × 0.25 mm
Z = 8

Data collection top

STOE IPDS 2 diffractometer	2104 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.071
Plane graphite monochromator	θ_max = 24.8°, θ_min = 4.1°
rotation method scans	h = −20→20
4793 measured reflections	k = 0→14
4793 independent reflections	l = 0→15

Refinement top

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0399P)²] where P = (F_o² + 2F_c²)/3
S = 0.73	(Δ/σ)_max = 0.002
4793 reflections	Δρ_max = 0.10 e Å⁻³
380 parameters	Δρ_min = −0.12 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: 0.0130 (9)

Crystal data top

C₁₈H₁₀N₂O	V = 2798.6 (5) Å³
M_r = 270.28	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.7196 (13) Å	µ = 0.08 mm⁻¹
b = 12.0092 (11) Å	T = 293 K
c = 13.2800 (19) Å	0.50 × 0.38 × 0.25 mm
β = 97.976 (8)°

Data collection top

STOE IPDS 2 diffractometer	2104 reflections with I > 2σ(I)
4793 measured reflections	R_int = 0.071
4793 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 0.73	Δρ_max = 0.10 e Å⁻³
4793 reflections	Δρ_min = −0.12 e Å⁻³
380 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
N2A	0.81170 (11)	0.24121 (17)	0.48224 (13)	0.1285 (6)
C2A	0.46155 (11)	0.32926 (19)	−0.09497 (15)	0.1129 (7)
H2A	0.4318	0.3917	−0.1135	0.135*
C3B	−0.04645 (11)	0.23947 (18)	0.18812 (16)	0.1077 (6)
H3B	−0.0858	0.2871	0.1622	0.129*
C2B	−0.03104 (12)	0.2227 (2)	0.29225 (15)	0.1116 (7)
H2B	−0.0606	0.2580	0.3353	0.134*
C3A	0.46902 (12)	0.2907 (2)	0.00445 (14)	0.1068 (7)
H3A	0.4442	0.3273	0.0522	0.128*
C1A	0.49693 (11)	0.27713 (19)	−0.16459 (13)	0.0977 (6)
H1A	0.4909	0.3040	−0.2309	0.117*
C18A	0.77846 (11)	0.20049 (17)	0.41281 (14)	0.0943 (6)
N2B	0.31272 (10)	0.24631 (15)	−0.32328 (12)	0.1187 (6)
C4B	−0.00498 (10)	0.18754 (17)	0.12341 (13)	0.0924 (6)
H4B	−0.0165	0.1987	0.0537	0.111*
C1B	0.02630 (12)	0.15575 (18)	0.33129 (13)	0.0966 (6)
H1B	0.0358	0.1450	0.4013	0.116*
C13A	0.74630 (10)	0.17575 (15)	0.22864 (12)	0.0868 (5)
H13A	0.7847	0.2257	0.2186	0.104*
C18B	0.27315 (11)	0.21891 (16)	−0.26765 (13)	0.0902 (5)
C13B	0.23715 (10)	0.20965 (15)	−0.09696 (12)	0.0870 (5)
H13B	0.2784	0.2551	−0.0734	0.104*
C14A	0.73408 (10)	0.14968 (15)	0.32613 (12)	0.0781 (5)
C4A	0.51219 (10)	0.20002 (17)	0.03213 (12)	0.0877 (5)
H4A	0.5162	0.1743	0.0987	0.105*
C6A	0.54310 (9)	0.18246 (16)	−0.13970 (11)	0.0769 (5)
C14B	0.22364 (10)	0.18146 (14)	−0.19811 (11)	0.0738 (4)
C12B	0.19061 (11)	0.17156 (15)	−0.03058 (12)	0.0873 (5)
H12B	0.2001	0.1911	0.0378	0.105*
C12A	0.70251 (10)	0.12888 (15)	0.14642 (12)	0.0827 (5)
H12A	0.7111	0.1467	0.0808	0.099*
C5B	0.05580 (9)	0.11644 (15)	0.16235 (11)	0.0738 (5)
C5A	0.55118 (9)	0.14383 (15)	−0.03843 (11)	0.0725 (4)
C6B	0.07229 (10)	0.10157 (14)	0.26853 (11)	0.0737 (4)
C7A	0.57911 (11)	0.12465 (19)	−0.21134 (12)	0.0928 (6)
H7A	0.5743	0.1502	−0.2780	0.111*
C15A	0.67749 (10)	0.07382 (15)	0.34082 (12)	0.0791 (5)
C15B	0.16095 (10)	0.11410 (14)	−0.23233 (10)	0.0711 (4)
C11B	0.12983 (10)	0.10439 (16)	−0.06492 (11)	0.0824 (5)
N1A	0.65917 (11)	0.0264 (2)	0.52442 (13)	0.1624 (9)
C17A	0.66577 (11)	0.04653 (18)	0.44250 (14)	0.1084 (7)
C17B	0.14519 (10)	0.08491 (15)	−0.33749 (13)	0.0854 (5)
C10B	0.10103 (11)	0.05969 (17)	0.10161 (12)	0.0875 (5)
O1B	0.07892 (6)	0.06690 (12)	−0.00415 (8)	0.1137 (5)
C16B	0.11404 (9)	0.07520 (14)	−0.16574 (11)	0.0786 (5)
H16B	0.0725	0.0301	−0.1885	0.094*
N1B	0.13383 (10)	0.06212 (15)	−0.42144 (11)	0.1203 (6)
C7B	0.13449 (12)	0.03463 (16)	0.30891 (13)	0.0917 (6)
H7B	0.1456	0.0250	0.3789	0.110*
C11A	0.64575 (10)	0.05529 (14)	0.16148 (12)	0.0753 (4)
C16A	0.63327 (9)	0.02714 (14)	0.25853 (12)	0.0840 (5)
H16A	0.5951	−0.0232	0.2682	0.101*
C10A	0.59558 (10)	0.04841 (16)	−0.01465 (12)	0.0790 (5)
C8A	0.62057 (11)	0.0325 (2)	−0.18487 (14)	0.1014 (6)
H8A	0.6437	−0.0052	−0.2335	0.122*
C9B	0.16033 (12)	−0.00475 (18)	0.14135 (16)	0.1046 (6)
H9B	0.1893	−0.0419	0.0986	0.125*
O1A	0.59936 (7)	0.00455 (10)	0.08423 (8)	0.0922 (4)
C8B	0.17799 (12)	−0.01548 (17)	0.24694 (16)	0.1047 (6)
H8B	0.2200	−0.0574	0.2744	0.126*
C9A	0.62908 (10)	−0.00697 (17)	−0.08439 (15)	0.0969 (6)
H9A	0.6576	−0.0707	−0.0663	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2A	0.1321 (15)	0.1572 (17)	0.0903 (11)	−0.0279 (13)	−0.0057 (10)	−0.0207 (11)
C2A	0.1148 (16)	0.1363 (19)	0.0873 (13)	0.0347 (14)	0.0133 (12)	0.0121 (13)
C3B	0.0841 (14)	0.1361 (18)	0.1031 (15)	0.0088 (12)	0.0136 (12)	−0.0071 (13)
C2B	0.0913 (16)	0.157 (2)	0.0881 (15)	0.0037 (15)	0.0183 (11)	−0.0274 (14)
C3A	0.1153 (17)	0.1296 (19)	0.0766 (13)	0.0283 (14)	0.0172 (11)	−0.0037 (12)
C1A	0.0972 (14)	0.1273 (18)	0.0678 (11)	0.0084 (13)	0.0085 (10)	0.0189 (12)
C18A	0.0937 (14)	0.1107 (16)	0.0769 (12)	−0.0093 (12)	0.0058 (11)	−0.0020 (11)
N2B	0.1137 (14)	0.1416 (15)	0.1020 (11)	−0.0128 (12)	0.0187 (10)	0.0467 (11)
C4B	0.0772 (13)	0.1258 (17)	0.0727 (11)	−0.0102 (12)	0.0059 (10)	0.0080 (11)
C1B	0.0942 (15)	0.1337 (17)	0.0632 (10)	−0.0141 (13)	0.0153 (10)	−0.0145 (11)
C13A	0.0853 (13)	0.0986 (14)	0.0750 (11)	−0.0181 (10)	0.0057 (9)	0.0019 (10)
C18B	0.0921 (13)	0.0986 (15)	0.0784 (11)	−0.0024 (11)	0.0064 (10)	0.0281 (10)
C13B	0.0959 (13)	0.0906 (13)	0.0713 (11)	−0.0139 (10)	0.0001 (10)	0.0051 (10)
C14A	0.0777 (12)	0.0858 (13)	0.0682 (11)	−0.0029 (10)	0.0011 (9)	0.0014 (9)
C4A	0.0940 (14)	0.1091 (16)	0.0600 (10)	−0.0012 (12)	0.0106 (9)	−0.0021 (10)
C6A	0.0717 (11)	0.1022 (14)	0.0562 (9)	−0.0068 (10)	0.0063 (8)	−0.0028 (9)
C14B	0.0796 (12)	0.0773 (12)	0.0635 (10)	0.0003 (10)	0.0067 (9)	0.0120 (9)
C12B	0.0986 (14)	0.0998 (14)	0.0620 (10)	−0.0082 (12)	0.0059 (10)	−0.0129 (10)
C12A	0.0850 (12)	0.0926 (13)	0.0697 (10)	−0.0093 (11)	0.0078 (9)	0.0075 (10)
C5B	0.0718 (11)	0.0949 (13)	0.0560 (9)	−0.0169 (10)	0.0133 (8)	−0.0027 (9)
C5A	0.0728 (11)	0.0872 (13)	0.0562 (9)	−0.0096 (10)	0.0040 (8)	−0.0049 (9)
C6B	0.0797 (12)	0.0863 (12)	0.0565 (9)	−0.0160 (10)	0.0146 (8)	−0.0041 (9)
C7A	0.0868 (14)	0.1280 (18)	0.0631 (10)	−0.0077 (13)	0.0087 (10)	−0.0047 (11)
C15A	0.0815 (12)	0.0909 (13)	0.0633 (10)	−0.0018 (11)	0.0043 (9)	0.0115 (9)
C15B	0.0827 (12)	0.0807 (12)	0.0500 (9)	0.0068 (10)	0.0093 (8)	0.0004 (8)
C11B	0.0823 (12)	0.1088 (14)	0.0587 (10)	−0.0053 (11)	0.0185 (9)	−0.0091 (9)
N1A	0.1650 (18)	0.238 (2)	0.0825 (11)	−0.0683 (17)	0.0094 (11)	0.0311 (14)
C17A	0.1045 (15)	0.1427 (19)	0.0748 (12)	−0.0278 (13)	0.0009 (10)	0.0164 (13)
C17B	0.0953 (13)	0.1014 (14)	0.0598 (10)	0.0023 (10)	0.0119 (9)	0.0011 (10)
C10B	0.0907 (14)	0.1153 (16)	0.0589 (11)	−0.0154 (12)	0.0186 (10)	−0.0105 (10)
O1B	0.0955 (9)	0.1905 (14)	0.0591 (7)	−0.0333 (9)	0.0247 (6)	−0.0196 (8)
C16B	0.0808 (11)	0.0998 (13)	0.0557 (9)	−0.0081 (10)	0.0118 (8)	−0.0097 (9)
N1B	0.1444 (15)	0.1533 (16)	0.0626 (9)	0.0009 (12)	0.0124 (9)	−0.0072 (10)
C7B	0.1025 (15)	0.1033 (15)	0.0696 (11)	−0.0080 (12)	0.0136 (10)	0.0123 (11)
C11A	0.0795 (12)	0.0749 (12)	0.0675 (10)	−0.0021 (10)	−0.0036 (9)	0.0039 (9)
C16A	0.0849 (12)	0.0888 (13)	0.0758 (11)	−0.0127 (10)	0.0023 (9)	0.0159 (10)
C10A	0.0852 (12)	0.0855 (14)	0.0635 (11)	−0.0095 (11)	0.0002 (9)	−0.0030 (10)
C8A	0.0975 (15)	0.1306 (19)	0.0765 (13)	−0.0004 (14)	0.0132 (10)	−0.0260 (12)
C9B	0.1084 (17)	0.1118 (17)	0.0989 (15)	0.0056 (13)	0.0333 (12)	−0.0146 (13)
O1A	0.1075 (9)	0.0897 (8)	0.0731 (7)	−0.0195 (7)	−0.0098 (6)	0.0064 (7)
C8B	0.1120 (16)	0.1040 (16)	0.0994 (15)	0.0122 (12)	0.0195 (12)	0.0146 (12)
C9A	0.0963 (14)	0.0991 (15)	0.0918 (13)	0.0090 (11)	0.0006 (11)	−0.0160 (12)

Geometric parameters (Å, º) top

N2A—C18A	1.134 (2)	C12B—H12B	0.9300
C2A—C1A	1.342 (2)	C12A—C11A	1.374 (2)
C2A—C3A	1.388 (2)	C12A—H12A	0.9300
C2A—H2A	0.9300	C5B—C10B	1.392 (2)
C3B—C4B	1.357 (2)	C5B—C6B	1.411 (2)
C3B—C2B	1.387 (2)	C5A—C10A	1.401 (2)
C3B—H3B	0.9300	C6B—C7B	1.409 (2)
C2B—C1B	1.342 (2)	C7A—C8A	1.347 (2)
C2B—H2B	0.9300	C7A—H7A	0.9300
C3A—C4A	1.352 (2)	C15A—C16A	1.373 (2)
C3A—H3A	0.9300	C15A—C17A	1.432 (2)
C1A—C6A	1.413 (2)	C15B—C16B	1.3766 (19)
C1A—H1A	0.9300	C15B—C17B	1.429 (2)
C18A—C14A	1.437 (2)	C11B—O1B	1.3675 (18)
N2B—C18B	1.136 (2)	C11B—C16B	1.3747 (19)
C4B—C5B	1.415 (2)	N1A—C17A	1.136 (2)
C4B—H4B	0.9300	C17B—N1B	1.1385 (18)
C1B—C6B	1.404 (2)	C10B—C9B	1.352 (2)
C1B—H1B	0.9300	C10B—O1B	1.4075 (18)
C13A—C12A	1.370 (2)	C16B—H16B	0.9300
C13A—C14A	1.378 (2)	C7B—C8B	1.345 (2)
C13A—H13A	0.9300	C7B—H7B	0.9300
C18B—C14B	1.432 (2)	C11A—O1A	1.3657 (17)
C13B—C12B	1.367 (2)	C11A—C16A	1.380 (2)
C13B—C14B	1.374 (2)	C16A—H16A	0.9300
C13B—H13B	0.9300	C10A—C9A	1.344 (2)
C14A—C15A	1.388 (2)	C10A—O1A	1.4078 (17)
C4A—C5A	1.411 (2)	C8A—C9A	1.404 (2)
C4A—H4A	0.9300	C8A—H8A	0.9300
C6A—C7A	1.401 (2)	C9B—C8B	1.400 (2)
C6A—C5A	1.4110 (19)	C9B—H9B	0.9300
C14B—C15B	1.398 (2)	C8B—H8B	0.9300
C12B—C11B	1.372 (2)	C9A—H9A	0.9300

C1A—C2A—C3A	120.50 (19)	C10A—C5A—C6A	117.60 (15)
C1A—C2A—H2A	119.7	C4A—C5A—C6A	118.78 (17)
C3A—C2A—H2A	119.7	C1B—C6B—C7B	121.76 (16)
C4B—C3B—C2B	121.04 (19)	C1B—C6B—C5B	118.55 (17)
C4B—C3B—H3B	119.5	C7B—C6B—C5B	119.68 (16)
C2B—C3B—H3B	119.5	C8A—C7A—C6A	120.86 (17)
C1B—C2B—C3B	120.40 (18)	C8A—C7A—H7A	119.6
C1B—C2B—H2B	119.8	C6A—C7A—H7A	119.6
C3B—C2B—H2B	119.8	C16A—C15A—C14A	119.98 (14)
C4A—C3A—C2A	120.21 (18)	C16A—C15A—C17A	121.03 (17)
C4A—C3A—H3A	119.9	C14A—C15A—C17A	118.99 (16)
C2A—C3A—H3A	119.9	C16B—C15B—C14B	120.72 (13)
C2A—C1A—C6A	121.67 (17)	C16B—C15B—C17B	119.40 (16)
C2A—C1A—H1A	119.2	C14B—C15B—C17B	119.88 (14)
C6A—C1A—H1A	119.2	O1B—C11B—C12B	123.31 (14)
N2A—C18A—C14A	178.1 (2)	O1B—C11B—C16B	115.41 (16)
C3B—C4B—C5B	119.82 (17)	C12B—C11B—C16B	121.20 (15)
C3B—C4B—H4B	120.1	N1A—C17A—C15A	177.4 (2)
C5B—C4B—H4B	120.1	N1B—C17B—C15B	178.9 (2)
C2B—C1B—C6B	121.26 (17)	C9B—C10B—C5B	122.21 (16)
C2B—C1B—H1B	119.4	C9B—C10B—O1B	121.23 (17)
C6B—C1B—H1B	119.4	C5B—C10B—O1B	116.44 (18)
C12A—C13A—C14A	120.68 (16)	C11B—O1B—C10B	119.61 (13)
C12A—C13A—H13A	119.7	C11B—C16B—C15B	118.66 (15)
C14A—C13A—H13A	119.7	C11B—C16B—H16B	120.7
N2B—C18B—C14B	178.5 (2)	C15B—C16B—H16B	120.7
C12B—C13B—C14B	120.62 (16)	C8B—C7B—C6B	120.45 (16)
C12B—C13B—H13B	119.7	C8B—C7B—H7B	119.8
C14B—C13B—H13B	119.7	C6B—C7B—H7B	119.8
C13A—C14A—C15A	119.46 (15)	O1A—C11A—C12A	123.64 (14)
C13A—C14A—C18A	121.09 (17)	O1A—C11A—C16A	115.76 (15)
C15A—C14A—C18A	119.45 (15)	C12A—C11A—C16A	120.60 (16)
C3A—C4A—C5A	121.02 (16)	C15A—C16A—C11A	119.72 (16)
C3A—C4A—H4A	119.5	C15A—C16A—H16A	120.1
C5A—C4A—H4A	119.5	C11A—C16A—H16A	120.1
C7A—C6A—C5A	119.26 (17)	C9A—C10A—C5A	122.51 (16)
C7A—C6A—C1A	122.92 (17)	C9A—C10A—O1A	119.30 (18)
C5A—C6A—C1A	117.80 (15)	C5A—C10A—O1A	117.96 (15)
C13B—C14B—C15B	118.90 (15)	C7A—C8A—C9A	120.53 (18)
C13B—C14B—C18B	120.94 (17)	C7A—C8A—H8A	119.7
C15B—C14B—C18B	120.16 (15)	C9A—C8A—H8A	119.7
C13B—C12B—C11B	119.89 (15)	C10B—C9B—C8B	119.82 (17)
C13B—C12B—H12B	120.1	C10B—C9B—H9B	120.1
C11B—C12B—H12B	120.1	C8B—C9B—H9B	120.1
C13A—C12A—C11A	119.56 (15)	C11A—O1A—C10A	118.66 (12)
C13A—C12A—H12A	120.2	C7B—C8B—C9B	120.29 (19)
C11A—C12A—H12A	120.2	C7B—C8B—H8B	119.9
C10B—C5B—C6B	117.46 (17)	C9B—C8B—H8B	119.9
C10B—C5B—C4B	123.65 (16)	C10A—C9A—C8A	119.23 (18)
C6B—C5B—C4B	118.90 (16)	C10A—C9A—H9A	120.4
C10A—C5A—C4A	123.57 (16)	C8A—C9A—H9A	120.4

C4B—C3B—C2B—C1B	1.1 (3)	C13B—C12B—C11B—O1B	−177.14 (17)
C1A—C2A—C3A—C4A	0.1 (3)	C13B—C12B—C11B—C16B	−0.7 (3)
C3A—C2A—C1A—C6A	−0.5 (3)	C6B—C5B—C10B—C9B	−2.1 (3)
C2B—C3B—C4B—C5B	−1.0 (3)	C4B—C5B—C10B—C9B	177.74 (18)
C3B—C2B—C1B—C6B	0.3 (3)	C6B—C5B—C10B—O1B	173.90 (14)
C12A—C13A—C14A—C15A	1.0 (3)	C4B—C5B—C10B—O1B	−6.2 (2)
C12A—C13A—C14A—C18A	−178.44 (17)	C12B—C11B—O1B—C10B	−24.0 (3)
C2A—C3A—C4A—C5A	0.9 (3)	C16B—C11B—O1B—C10B	159.39 (17)
C2A—C1A—C6A—C7A	178.29 (18)	C9B—C10B—O1B—C11B	−59.4 (3)
C2A—C1A—C6A—C5A	−0.1 (3)	C5B—C10B—O1B—C11B	124.50 (17)
C12B—C13B—C14B—C15B	0.7 (3)	O1B—C11B—C16B—C15B	177.18 (15)
C12B—C13B—C14B—C18B	−178.54 (17)	C12B—C11B—C16B—C15B	0.5 (3)
C14B—C13B—C12B—C11B	0.1 (3)	C14B—C15B—C16B—C11B	0.3 (2)
C14A—C13A—C12A—C11A	0.1 (3)	C17B—C15B—C16B—C11B	−179.76 (16)
C3B—C4B—C5B—C10B	179.78 (17)	C1B—C6B—C7B—C8B	−179.41 (17)
C3B—C4B—C5B—C6B	−0.4 (3)	C5B—C6B—C7B—C8B	−0.3 (3)
C3A—C4A—C5A—C10A	−178.80 (17)	C13A—C12A—C11A—O1A	−179.98 (16)
C3A—C4A—C5A—C6A	−1.4 (3)	C13A—C12A—C11A—C16A	−0.9 (3)
C7A—C6A—C5A—C10A	0.1 (2)	C14A—C15A—C16A—C11A	0.5 (3)
C1A—C6A—C5A—C10A	178.55 (16)	C17A—C15A—C16A—C11A	179.81 (16)
C7A—C6A—C5A—C4A	−177.47 (15)	O1A—C11A—C16A—C15A	179.73 (15)
C1A—C6A—C5A—C4A	1.0 (2)	C12A—C11A—C16A—C15A	0.6 (3)
C2B—C1B—C6B—C7B	177.45 (18)	C4A—C5A—C10A—C9A	176.56 (16)
C2B—C1B—C6B—C5B	−1.7 (3)	C6A—C5A—C10A—C9A	−0.9 (2)
C10B—C5B—C6B—C1B	−178.45 (15)	C4A—C5A—C10A—O1A	2.1 (2)
C4B—C5B—C6B—C1B	1.7 (2)	C6A—C5A—C10A—O1A	−175.41 (13)
C10B—C5B—C6B—C7B	2.4 (2)	C6A—C7A—C8A—C9A	−0.5 (3)
C4B—C5B—C6B—C7B	−177.48 (16)	C5B—C10B—C9B—C8B	−0.3 (3)
C5A—C6A—C7A—C8A	0.6 (3)	O1B—C10B—C9B—C8B	−176.11 (16)
C1A—C6A—C7A—C8A	−177.76 (18)	C12A—C11A—O1A—C10A	−16.4 (2)
C13A—C14A—C15A—C16A	−1.3 (3)	C16A—C11A—O1A—C10A	164.50 (15)
C18A—C14A—C15A—C16A	178.13 (17)	C9A—C10A—O1A—C11A	107.21 (18)
C13A—C14A—C15A—C17A	179.41 (17)	C5A—C10A—O1A—C11A	−78.10 (19)
C18A—C14A—C15A—C17A	−1.2 (3)	C6B—C7B—C8B—C9B	−2.2 (3)
C13B—C14B—C15B—C16B	−0.9 (2)	C10B—C9B—C8B—C7B	2.5 (3)
C18B—C14B—C15B—C16B	178.32 (16)	C5A—C10A—C9A—C8A	1.0 (3)
C13B—C14B—C15B—C17B	179.18 (15)	O1A—C10A—C9A—C8A	175.40 (15)
C18B—C14B—C15B—C17B	−1.6 (2)	C7A—C8A—C9A—C10A	−0.2 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₀N₂O
M_r	270.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.7196 (13), 12.0092 (11), 13.2800 (19)
β (°)	97.976 (8)
V (Å³)	2798.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.38 × 0.25

Data collection
Diffractometer	STOE IPDS 2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4793, 4793, 2104
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.590

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.074, 0.73
No. of reflections	4793
No. of parameters	380
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.12

Computer programs: STOE X-AREA (Stoe & Cie, 2002), STOE X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1999) and PLATON (Spek, 1997).

Selected geometric parameters (Å, º) top

N2A—C18A	1.134 (2)	C11B—O1B	1.3675 (18)
C18A—C14A	1.437 (2)	N1A—C17A	1.136 (2)
N2B—C18B	1.136 (2)	C17B—N1B	1.1385 (18)
C18B—C14B	1.432 (2)	C10B—O1B	1.4075 (18)
C15A—C17A	1.432 (2)	C11A—O1A	1.3657 (17)
C15B—C17B	1.429 (2)	C10A—O1A	1.4078 (17)

C15A—C14A—C18A	119.45 (15)	C11B—O1B—C10B	119.61 (13)
C15B—C14B—C18B	120.16 (15)	O1A—C11A—C12A	123.64 (14)
O1B—C11B—C12B	123.31 (14)	O1A—C11A—C16A	115.76 (15)
O1B—C11B—C16B	115.41 (16)	C9A—C10A—O1A	119.30 (18)
C9B—C10B—O1B	121.23 (17)	C5A—C10A—O1A	117.96 (15)
C5B—C10B—O1B	116.44 (18)	C11A—O1A—C10A	118.66 (12)

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