Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045138/ci2458sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045138/ci2458Isup2.hkl |
CCDC reference: 667271
The title compound was prepared using the method reported previously by Agar et al. (1999).
Atoms C17 and C18 of the allyl group are disordered over two sites, with refined occupancies of 0.695 (6) and 0.305 (6). The corresponding C—C distances involving the disordered atoms were restrained to be the same. The H atoms of the benzene rings were located in a difference map and refined freely, with Uiso(H) = 1.2Ueq(C). All other H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C). 1315 Friedel pairs were merged before the final refinement.
Phthalonitriles have been used as starting materials for phthalocyanines (Leznoff & Lever, 1996), which are important components for dyes, pigments, gas sensors, optical limiters and liquid crystals, and which are also used in medicine, as singlet oxygen photosensitisers for photodynamic therapy (PDT) (McKeown, 1998). Some phthalocyanines have been used in the petroleum industry as catalysts, for the oxidation of sulfur compounds in the gasoline fraction. Applications as photoconductors in the xerographic double layers of laser printers and copying machines, and as active materials in writable data-storage disks, are also known (Wöhrle, 2001). The synthetic details of the title compound was published elsewhere (Agar et al., 1999). We report here the crystal structure of the title compound.
The benzene rings are essentially planar [the atoms having the largest deviations in the two benzene rings are C4 (0.009 (2) Å) and C12 (0.017 (2) Å)] and they form a dihedral angle of 88.6 (1)° (Fig. 1). The methoxy group is coplanar with the attached ring, with the C13—C14—O2—C15 torsion angle being 0.6 (4)°.
The crystal packing is stabilized by C—H···N intermolecular hydrogen bonds and C—H···π interactions (Table 1). The C—H···N hydrogen bonds link the molecules into a C(6) chain along the a axis (Fig. 2). The chain is further strengthened by C16—H16A···π interactions involving the C1—C6 benzene ring (centroid Cg1).
For general background, see: Agar et al. (1999); Leznoff & Lever (1996); McKeown (1998); Wöhrle (2001).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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 (Farrugia, 1999).
C18H14N2O2 | F(000) = 608 |
Mr = 290.31 | Dx = 1.265 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 11502 reflections |
a = 14.7784 (13) Å | θ = 1.7–27.8° |
b = 11.9726 (9) Å | µ = 0.08 mm−1 |
c = 8.6133 (6) Å | T = 296 K |
V = 1524.0 (2) Å3 | Prism, colourless |
Z = 4 | 0.78 × 0.40 × 0.17 mm |
Stoe IPDSII diffractometer | 1930 independent reflections |
Radiation source: fine-focus sealed tube | 1317 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.0°, θmin = 2.2° |
ω scans | h = −19→19 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.969, Tmax = 0.989 | l = −10→11 |
14749 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3 |
1930 reflections | (Δ/σ)max = 0.001 |
225 parameters | Δρmax = 0.08 e Å−3 |
3 restraints | Δρmin = −0.10 e Å−3 |
C18H14N2O2 | V = 1524.0 (2) Å3 |
Mr = 290.31 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.7784 (13) Å | µ = 0.08 mm−1 |
b = 11.9726 (9) Å | T = 296 K |
c = 8.6133 (6) Å | 0.78 × 0.40 × 0.17 mm |
Stoe IPDSII diffractometer | 1930 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1317 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.989 | Rint = 0.074 |
14749 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 3 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.91 | Δρmax = 0.08 e Å−3 |
1930 reflections | Δρmin = −0.10 e Å−3 |
225 parameters |
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 | Occ. (<1) | |
O1 | 0.49053 (11) | 0.51155 (13) | 0.3686 (2) | 0.0736 (5) | |
O2 | 0.53129 (11) | 0.33713 (16) | 0.1909 (2) | 0.0828 (5) | |
N1 | 0.36210 (17) | 0.1802 (2) | 0.8284 (4) | 0.1042 (9) | |
N2 | 0.12638 (15) | 0.2620 (2) | 0.6747 (4) | 0.0956 (7) | |
C1 | 0.41981 (14) | 0.45549 (17) | 0.4342 (3) | 0.0608 (5) | |
C2 | 0.42998 (15) | 0.37518 (17) | 0.5476 (3) | 0.0617 (5) | |
H2 | 0.4858 (17) | 0.352 (2) | 0.584 (3) | 0.074* | |
C3 | 0.35322 (14) | 0.32673 (17) | 0.6111 (3) | 0.0613 (5) | |
C4 | 0.26687 (14) | 0.35687 (18) | 0.5590 (3) | 0.0642 (5) | |
C5 | 0.25886 (15) | 0.4388 (2) | 0.4455 (3) | 0.0708 (6) | |
H5 | 0.1964 (18) | 0.462 (2) | 0.410 (3) | 0.085* | |
C6 | 0.33423 (16) | 0.4874 (2) | 0.3835 (3) | 0.0682 (6) | |
H6 | 0.3309 (15) | 0.543 (2) | 0.302 (4) | 0.082* | |
C7 | 0.36038 (15) | 0.2447 (2) | 0.7318 (3) | 0.0740 (6) | |
C8 | 0.18843 (16) | 0.3044 (2) | 0.6234 (3) | 0.0730 (6) | |
C9 | 0.57803 (13) | 0.46782 (19) | 0.3737 (3) | 0.0642 (5) | |
C10 | 0.64291 (18) | 0.5200 (2) | 0.4616 (4) | 0.0764 (6) | |
H10 | 0.6209 (17) | 0.576 (2) | 0.528 (4) | 0.092* | |
C11 | 0.73302 (17) | 0.4895 (2) | 0.4442 (4) | 0.0790 (7) | |
H11 | 0.7764 (19) | 0.531 (2) | 0.516 (4) | 0.095* | |
C12 | 0.75807 (15) | 0.4089 (2) | 0.3391 (3) | 0.0732 (6) | |
C13 | 0.69107 (16) | 0.3541 (2) | 0.2541 (3) | 0.0710 (6) | |
H13 | 0.7080 (17) | 0.296 (2) | 0.174 (4) | 0.085* | |
C14 | 0.60094 (15) | 0.38315 (18) | 0.2714 (3) | 0.0669 (6) | |
C15 | 0.5531 (2) | 0.2518 (2) | 0.0813 (4) | 0.0978 (9) | |
H15A | 0.5949 | 0.2806 | 0.0061 | 0.147* | |
H15B | 0.4989 | 0.2276 | 0.0297 | 0.147* | |
H15C | 0.5801 | 0.1896 | 0.1344 | 0.147* | |
C16 | 0.85578 (17) | 0.3797 (3) | 0.3059 (4) | 0.0944 (9) | |
H16A | 0.8696 | 0.3101 | 0.3583 | 0.113* | 0.695 (6) |
H16C | 0.8618 | 0.3665 | 0.1953 | 0.113* | 0.695 (6) |
H16D | 0.8699 | 0.4052 | 0.2030 | 0.113* | 0.305 (6) |
H16B | 0.8615 | 0.2999 | 0.3060 | 0.113* | 0.305 (6) |
C17A | 0.9235 (3) | 0.4622 (4) | 0.3515 (7) | 0.0994 (15) | 0.695 (6) |
H17A | 0.9160 | 0.5350 | 0.3159 | 0.119* | 0.695 (6) |
C18A | 0.9929 (3) | 0.4418 (6) | 0.4376 (8) | 0.124 (2) | 0.695 (6) |
H18A | 1.0026 | 0.3700 | 0.4754 | 0.148* | 0.695 (6) |
H18B | 1.0333 | 0.4987 | 0.4618 | 0.148* | 0.695 (6) |
C17B | 0.9235 (6) | 0.4196 (9) | 0.4153 (14) | 0.0994 (15) | 0.305 (6) |
H17B | 0.9228 | 0.3906 | 0.5155 | 0.119* | 0.305 (6) |
C18B | 0.9847 (10) | 0.4930 (13) | 0.382 (3) | 0.124 (2) | 0.305 (6) |
H18C | 0.9872 | 0.5235 | 0.2825 | 0.148* | 0.305 (6) |
H18D | 1.0263 | 0.5152 | 0.4567 | 0.148* | 0.305 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0676 (8) | 0.0717 (9) | 0.0815 (12) | 0.0061 (7) | 0.0087 (8) | 0.0191 (9) |
O2 | 0.0739 (9) | 0.0871 (11) | 0.0874 (13) | −0.0033 (8) | −0.0090 (9) | −0.0118 (10) |
N1 | 0.1000 (16) | 0.1026 (17) | 0.110 (2) | −0.0132 (13) | −0.0126 (14) | 0.0421 (17) |
N2 | 0.0752 (13) | 0.1035 (16) | 0.108 (2) | −0.0108 (12) | 0.0071 (13) | −0.0001 (15) |
C1 | 0.0660 (12) | 0.0597 (11) | 0.0568 (13) | 0.0000 (9) | 0.0044 (9) | −0.0005 (10) |
C2 | 0.0622 (11) | 0.0620 (11) | 0.0607 (14) | 0.0009 (9) | −0.0053 (10) | −0.0006 (10) |
C3 | 0.0697 (12) | 0.0576 (11) | 0.0567 (13) | −0.0039 (9) | −0.0022 (9) | −0.0003 (10) |
C4 | 0.0609 (11) | 0.0682 (12) | 0.0636 (14) | −0.0013 (9) | 0.0013 (10) | −0.0050 (11) |
C5 | 0.0656 (13) | 0.0756 (13) | 0.0711 (16) | 0.0084 (10) | −0.0023 (11) | 0.0017 (13) |
C6 | 0.0718 (13) | 0.0713 (14) | 0.0616 (15) | 0.0088 (10) | −0.0010 (11) | 0.0061 (12) |
C7 | 0.0703 (13) | 0.0751 (13) | 0.0766 (17) | −0.0089 (10) | −0.0071 (12) | 0.0100 (13) |
C8 | 0.0634 (12) | 0.0784 (13) | 0.0772 (17) | −0.0002 (11) | 0.0007 (11) | −0.0007 (13) |
C9 | 0.0631 (12) | 0.0650 (12) | 0.0646 (14) | −0.0006 (9) | 0.0042 (10) | 0.0100 (11) |
C10 | 0.0858 (16) | 0.0753 (14) | 0.0680 (17) | −0.0058 (12) | 0.0048 (13) | 0.0063 (13) |
C11 | 0.0739 (14) | 0.0878 (15) | 0.0753 (17) | −0.0131 (12) | −0.0074 (13) | 0.0062 (14) |
C12 | 0.0677 (12) | 0.0778 (13) | 0.0743 (18) | −0.0015 (11) | −0.0009 (11) | 0.0156 (13) |
C13 | 0.0700 (14) | 0.0703 (13) | 0.0727 (16) | 0.0021 (11) | 0.0026 (12) | 0.0040 (13) |
C14 | 0.0651 (11) | 0.0704 (13) | 0.0652 (14) | −0.0038 (10) | −0.0036 (10) | 0.0089 (11) |
C15 | 0.101 (2) | 0.0907 (17) | 0.102 (2) | −0.0066 (14) | −0.0140 (17) | −0.0210 (17) |
C16 | 0.0680 (14) | 0.104 (2) | 0.111 (3) | −0.0034 (13) | −0.0023 (14) | 0.0154 (19) |
C17A | 0.0668 (18) | 0.090 (3) | 0.141 (5) | 0.000 (2) | −0.001 (2) | 0.035 (3) |
C18A | 0.085 (2) | 0.135 (6) | 0.151 (7) | −0.016 (3) | −0.031 (3) | 0.022 (4) |
C17B | 0.0668 (18) | 0.090 (3) | 0.141 (5) | 0.000 (2) | −0.001 (2) | 0.035 (3) |
C18B | 0.085 (2) | 0.135 (6) | 0.151 (7) | −0.016 (3) | −0.031 (3) | 0.022 (4) |
O1—C1 | 1.364 (3) | C11—H11 | 1.02 (3) |
O1—C9 | 1.396 (3) | C12—C13 | 1.395 (4) |
O2—C14 | 1.358 (3) | C12—C16 | 1.513 (4) |
O2—C15 | 1.428 (3) | C13—C14 | 1.385 (3) |
N1—C7 | 1.136 (3) | C13—H13 | 1.02 (3) |
N2—C8 | 1.137 (3) | C15—H15A | 0.96 |
C1—C2 | 1.379 (3) | C15—H15B | 0.96 |
C1—C6 | 1.391 (3) | C15—H15C | 0.96 |
C2—C3 | 1.386 (3) | C16—C17B | 1.456 (9) |
C2—H2 | 0.93 (3) | C16—C17A | 1.460 (5) |
C3—C4 | 1.400 (3) | C16—H16A | 0.97 |
C3—C7 | 1.434 (4) | C16—H16C | 0.97 |
C4—C5 | 1.390 (3) | C16—H16D | 0.96 |
C4—C8 | 1.431 (3) | C16—H16B | 0.96 |
C5—C6 | 1.366 (4) | C17A—C18A | 1.289 (6) |
C5—H5 | 1.01 (3) | C17A—H17A | 0.93 |
C6—H6 | 0.97 (3) | C18A—H18A | 0.93 |
C9—C10 | 1.372 (4) | C18A—H18B | 0.93 |
C9—C14 | 1.385 (4) | C17B—C18B | 1.294 (9) |
C10—C11 | 1.389 (4) | C17B—H17B | 0.93 |
C10—H10 | 0.94 (3) | C18B—H18C | 0.93 |
C11—C12 | 1.374 (4) | C18B—H18D | 0.93 |
C1—O1—C9 | 120.80 (16) | O2—C14—C13 | 124.9 (2) |
C14—O2—C15 | 117.20 (19) | O2—C14—C9 | 115.89 (19) |
O1—C1—C2 | 123.6 (2) | C13—C14—C9 | 119.2 (2) |
O1—C1—C6 | 115.6 (2) | O2—C15—H15A | 109.5 |
C2—C1—C6 | 120.8 (2) | O2—C15—H15B | 109.5 |
C1—C2—C3 | 118.8 (2) | H15A—C15—H15B | 109.5 |
C1—C2—H2 | 123.2 (16) | O2—C15—H15C | 109.5 |
C3—C2—H2 | 118.0 (16) | H15A—C15—H15C | 109.5 |
C2—C3—C4 | 120.8 (2) | H15B—C15—H15C | 109.5 |
C2—C3—C7 | 120.8 (2) | C17B—C16—C12 | 117.3 (6) |
C4—C3—C7 | 118.4 (2) | C17A—C16—C12 | 116.6 (3) |
C5—C4—C3 | 119.0 (2) | C17A—C16—H16A | 108.1 |
C5—C4—C8 | 120.9 (2) | C12—C16—H16A | 108.1 |
C3—C4—C8 | 120.1 (2) | C17B—C16—H16C | 128.8 |
C6—C5—C4 | 120.4 (2) | C17A—C16—H16C | 108.1 |
C6—C5—H5 | 120.3 (15) | C12—C16—H16C | 108.1 |
C4—C5—H5 | 119.2 (15) | H16A—C16—H16C | 107.3 |
C5—C6—C1 | 120.1 (2) | C17B—C16—H16D | 110.1 |
C5—C6—H6 | 122.4 (14) | C12—C16—H16D | 108.0 |
C1—C6—H6 | 117.5 (14) | H16A—C16—H16D | 131.0 |
N1—C7—C3 | 177.0 (3) | C17B—C16—H16B | 105.4 |
N2—C8—C4 | 179.6 (3) | C17A—C16—H16B | 127.8 |
C10—C9—C14 | 120.9 (2) | C12—C16—H16B | 108.3 |
C10—C9—O1 | 119.6 (2) | H16D—C16—H16B | 107.3 |
C14—C9—O1 | 118.8 (2) | C18A—C17A—C16 | 124.9 (5) |
C9—C10—C11 | 119.4 (3) | C18A—C17A—H17A | 117.6 |
C9—C10—H10 | 114.7 (17) | C16—C17A—H17A | 117.6 |
C11—C10—H10 | 125.8 (16) | C17A—C18A—H18A | 120.0 |
C12—C11—C10 | 120.9 (3) | C17A—C18A—H18B | 120.0 |
C12—C11—H11 | 125.0 (17) | H18A—C18A—H18B | 120.0 |
C10—C11—H11 | 114.0 (17) | C18B—C17B—C16 | 123.9 (13) |
C11—C12—C13 | 119.0 (2) | C18B—C17B—H17B | 118.0 |
C11—C12—C16 | 122.9 (2) | C16—C17B—H17B | 118.0 |
C13—C12—C16 | 118.0 (3) | C17B—C18B—H18C | 120.0 |
C14—C13—C12 | 120.5 (2) | C17B—C18B—H18D | 120.0 |
C14—C13—H13 | 118.9 (15) | H18C—C18B—H18D | 120.0 |
C12—C13—H13 | 120.4 (15) | ||
C9—O1—C1—C2 | 21.1 (3) | C10—C11—C12—C13 | −2.8 (4) |
C9—O1—C1—C6 | −161.3 (2) | C10—C11—C12—C16 | 174.6 (3) |
O1—C1—C2—C3 | 177.3 (2) | C11—C12—C13—C14 | 2.3 (4) |
C6—C1—C2—C3 | −0.2 (3) | C16—C12—C13—C14 | −175.3 (2) |
C1—C2—C3—C4 | 1.3 (3) | C15—O2—C14—C13 | 0.6 (4) |
C1—C2—C3—C7 | −178.6 (2) | C15—O2—C14—C9 | 178.3 (2) |
C2—C3—C4—C5 | −1.9 (3) | C12—C13—C14—O2 | 178.0 (2) |
C7—C3—C4—C5 | 178.0 (2) | C12—C13—C14—C9 | 0.3 (3) |
C2—C3—C4—C8 | 178.7 (2) | C10—C9—C14—O2 | 179.7 (2) |
C7—C3—C4—C8 | −1.4 (3) | O1—C9—C14—O2 | −10.3 (3) |
C3—C4—C5—C6 | 1.4 (3) | C10—C9—C14—C13 | −2.4 (4) |
C8—C4—C5—C6 | −179.2 (2) | O1—C9—C14—C13 | 167.6 (2) |
C4—C5—C6—C1 | −0.3 (4) | C11—C12—C16—C17B | 14.8 (6) |
O1—C1—C6—C5 | −178.0 (2) | C13—C12—C16—C17B | −167.7 (5) |
C2—C1—C6—C5 | −0.3 (4) | C11—C12—C16—C17A | −18.7 (5) |
C1—O1—C9—C10 | −111.8 (2) | C13—C12—C16—C17A | 158.7 (3) |
C1—O1—C9—C14 | 78.0 (3) | C17B—C16—C17A—C18A | 27.7 (11) |
C14—C9—C10—C11 | 1.9 (4) | C12—C16—C17A—C18A | 126.7 (6) |
O1—C9—C10—C11 | −168.0 (2) | C17A—C16—C17B—C18B | −17.3 (12) |
C9—C10—C11—C12 | 0.8 (4) | C12—C16—C17B—C18B | −113.7 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N2i | 0.93 (3) | 2.61 (3) | 3.510 (3) | 166 (2) |
C16—H16A···Cg1i | 0.97 | 2.88 | 3.808 (4) | 160 |
Symmetry code: (i) x+1/2, −y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C18H14N2O2 |
Mr | 290.31 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 296 |
a, b, c (Å) | 14.7784 (13), 11.9726 (9), 8.6133 (6) |
V (Å3) | 1524.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.78 × 0.40 × 0.17 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.969, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14749, 1930, 1317 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.099, 0.91 |
No. of reflections | 1930 |
No. of parameters | 225 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.08, −0.10 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N2i | 0.93 (3) | 2.61 (3) | 3.510 (3) | 166 (2) |
C16—H16A···Cg1i | 0.97 | 2.88 | 3.808 (4) | 160 |
Symmetry code: (i) x+1/2, −y+1/2, z. |
Phthalonitriles have been used as starting materials for phthalocyanines (Leznoff & Lever, 1996), which are important components for dyes, pigments, gas sensors, optical limiters and liquid crystals, and which are also used in medicine, as singlet oxygen photosensitisers for photodynamic therapy (PDT) (McKeown, 1998). Some phthalocyanines have been used in the petroleum industry as catalysts, for the oxidation of sulfur compounds in the gasoline fraction. Applications as photoconductors in the xerographic double layers of laser printers and copying machines, and as active materials in writable data-storage disks, are also known (Wöhrle, 2001). The synthetic details of the title compound was published elsewhere (Agar et al., 1999). We report here the crystal structure of the title compound.
The benzene rings are essentially planar [the atoms having the largest deviations in the two benzene rings are C4 (0.009 (2) Å) and C12 (0.017 (2) Å)] and they form a dihedral angle of 88.6 (1)° (Fig. 1). The methoxy group is coplanar with the attached ring, with the C13—C14—O2—C15 torsion angle being 0.6 (4)°.
The crystal packing is stabilized by C—H···N intermolecular hydrogen bonds and C—H···π interactions (Table 1). The C—H···N hydrogen bonds link the molecules into a C(6) chain along the a axis (Fig. 2). The chain is further strengthened by C16—H16A···π interactions involving the C1—C6 benzene ring (centroid Cg1).