7-tert-Butyl-1,3-bis­(eth­oxy­meth­yl)pyrene

Moriguchi, T.; Sasaki, M.; Miyoshi, N.

doi:10.1107/S241431462600413X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 4| April 2026| x260413

https://doi.org/10.1107/S241431462600413X

Open

access

7-tert-Butyl-1,3-bis(ethoxymethyl)pyrene

Tetsuji Moriguchi,^a ^* Misa Sasaki ^a and Noriko Miyoshi ^b

^aDepartment of Material Science, Faculty of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku Kitakyushu, Fukuoka, Japan, and ^bTechnical Support Department, Management Headquarters, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 6 March 2026; accepted 20 April 2026; online 29 April 2026)

In the molecular structure of the title compound, C₂₆H₃₀O₂, the two ethoxymethyl side arms are twisted from the almost planar pyrene system by 29.85 (17) and 15.16 (18)°. In the crystal, adjacent molecules are arranged in pairs that mainly interact through π–π interactions.

Keywords: crystal structure; substituted pyrene derivative; π–π interactions.

CCDC reference: 2547421

Structure description

In recent years, polycyclic aromatic hydrocarbons (PAHs) have been attracting great interest owing to their significant photochemical and electrical properties (Dötz et al., 2000 ). In the PAHs, pyrene and its derivatives are probably the most studied compounds. They constitute an important class of PAHs found in charcoal and are valuable as intermediates. Moreover, the PAHs comprising the pyrene moiety exhibit p-type semiconductor properties (Moriguchi et al., 2017 ). In the context of our previous studies with respect to substituted pyrene derivatives (Moriguchi et al., 2015 ; Moriguchi et al., 2018 ) or a lanthanum complex with four pyrene moieties (Moriguchi et al., 2014 ), in order to evaluate its fluorescence properties, we report here the result of the crystal structure analysis of 7-tert-butyl-1,3-bis(ethoxymethyl)pyrene.

The molecular structure is shown in Fig. 1. The pyrene ring system is almost planar, with an r.m.s. deviation of the non-H atoms of 0.011 Å. The dihedral angles between the planes of the pyrene system and the ethoxymethyl groups are 29.85 (17) (C21/O1/C23/C24) and 15.16 (18)° (C22/O2/C25/C26).

Figure 1
The molecular structure and atom-numbering scheme for the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.

The packing of the molecules within the unit cell is shown in Fig. 2. A particular arrangement results from π–π interactions between molecules arranged in pairs (Fig. 3), with centroid-to-centroid distances of Cg1⋯Cg3′ of 3.6216 (8) Å (slippage 1.115 Å), Cg1⋯Cg2′ of 3.9104 (8) Å (slippage 1.840 Å), Cg1⋯Cg4′ of 3.7156 (8) Å (slippage 1.408 Å) and Cg3⋯Cg2′ of 3.7092 (8) Å (slippage 1.403 Å) [Cg1 is the centroid of ring C1–C4/C14/C15 (plane 1), Cg2 is the centroid of ring C11–C16 (plane 2), Cg3 is the centroid of ring C4–C7/C15/C16 (plane 3) and Cg4 is the centroid of ring C7–C11/C16 (plane 4); symmetry code for primed centroids: −x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , −z]. These values are approximately equal or smaller than the sum of the van der Waals radii of aromatic planes (Rowland & Taylor, 1996 ).

Figure 2
Packing diagram of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.

Figure 3
A pair of molecules linked by intermolecular π–π interactions and definitions of the planes. The molecule with primed labels is related by symmetry code (−x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , −z).

Synthesis and crystallization

A tetrahydrofuran solution (50 ml) of 4-tert-butyl-1,3-bis(chloromethyl)pyrene (0.10 mmol) was added dropwise to ethanol (1 mmol) in the presence of an excess of sodium (0.5 mmol). The mixed solution was then stirred for 3 h at room temperature before the volatiles were removed under reduced pressure. The crude reaction mixture was subjected to column chromatography using EtOAc/hexane as the mobile phase. The title compound was isolated as a yellow fluorescent solid with 80% yield. Single crystals were obtained by the vapour diffusion method at room temperature by diffusion of hexane into a chloroform solution. MS: M⁺, 374.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₆H₃₀O₂
M_r	374.50
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	90
a, b, c (Å)	31.563 (2), 13.4849 (10), 9.4170 (7)
β (°)	92.464 (1)
V (Å³)	4004.4 (5)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.35 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.666, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	23061, 4876, 3900
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.173, 1.05
No. of reflections	4876
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.47
Computer programs: SMART and SAINT (Bruker, 2009 ), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2547421

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431462600413X/wm4247sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462600413X/wm4247Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431462600413X/wm4247Isup3.cml

checkCIF report

Computing details top

7-tert-Butyl-1,3-bis(ethoxymethyl)pyrene top

Crystal data top

C₂₆H₃₀O₂	F(000) = 1616
M_r = 374.50	D_x = 1.242 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 31.563 (2) Å	Cell parameters from 7217 reflections
b = 13.4849 (10) Å	θ = 2.5–28.5°
c = 9.4170 (7) Å	µ = 0.08 mm⁻¹
β = 92.464 (1)°	T = 90 K
V = 4004.4 (5) Å³	Prism, clear light colourless
Z = 8	0.50 × 0.35 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	4876 independent reflections
Radiation source: sealed tube	3900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8 pixels mm^-1	θ_max = 28.7°, θ_min = 1.6°
φ and ω scans	h = −40→41
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −17→18
T_min = 0.666, T_max = 0.746	l = −12→12
23061 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.0977P)² + 3.0623P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4876 reflections	Δρ_max = 0.46 e Å⁻³
258 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.12093 (3)	0.49719 (8)	0.09130 (12)	0.0282 (3)
O2	0.14358 (3)	0.23373 (8)	0.39513 (11)	0.0264 (3)
C1	0.18957 (4)	0.41990 (10)	0.09130 (14)	0.0202 (3)
C2	0.17553 (4)	0.35367 (10)	0.19234 (14)	0.0200 (3)
H2	0.147300	0.356026	0.216684	0.024*
C3	0.20235 (4)	0.28392 (10)	0.25827 (13)	0.0189 (3)
C4	0.24518 (4)	0.27928 (10)	0.22227 (13)	0.0184 (3)
C5	0.27447 (4)	0.20736 (10)	0.28424 (14)	0.0207 (3)
H5	0.264937	0.162385	0.350582	0.025*
C6	0.31544 (4)	0.20404 (11)	0.24785 (14)	0.0221 (3)
H6	0.333469	0.156872	0.289762	0.026*
C7	0.33165 (4)	0.27162 (10)	0.14618 (14)	0.0208 (3)
C8	0.37391 (4)	0.26903 (11)	0.10699 (15)	0.0242 (3)
H8	0.392067	0.222113	0.148895	0.029*
C9	0.38982 (4)	0.33436 (11)	0.00726 (15)	0.0249 (3)
C10	0.36178 (4)	0.40291 (11)	−0.05576 (15)	0.0237 (3)
H10	0.371724	0.446394	−0.123375	0.028*
C11	0.31912 (4)	0.40857 (10)	−0.02072 (14)	0.0208 (3)
C12	0.29017 (4)	0.47819 (11)	−0.08668 (15)	0.0230 (3)
H12	0.299875	0.521467	−0.154981	0.028*
C13	0.24900 (4)	0.48248 (10)	−0.05191 (15)	0.0220 (3)
H13	0.231062	0.528372	−0.097248	0.026*
C14	0.23239 (4)	0.41764 (10)	0.05358 (14)	0.0197 (3)
C15	0.26024 (4)	0.34700 (10)	0.12030 (13)	0.0180 (3)
C16	0.30358 (4)	0.34268 (10)	0.08249 (14)	0.0190 (3)
C17	0.43655 (5)	0.32752 (13)	−0.02992 (17)	0.0297 (3)
C18	0.44405 (6)	0.22943 (15)	−0.1055 (2)	0.0440 (5)
H18A	0.436099	0.175498	−0.045671	0.066*
H18B	0.473517	0.223630	−0.125507	0.066*
H18C	0.427258	0.227436	−0.192908	0.066*
C19	0.46469 (6)	0.3341 (2)	0.1055 (2)	0.0526 (6)
H19A	0.458905	0.394888	0.154212	0.079*
H19B	0.493939	0.332769	0.081555	0.079*
H19C	0.458934	0.278932	0.166122	0.079*
C20	0.44954 (6)	0.41281 (16)	−0.1274 (2)	0.0488 (5)
H20A	0.432821	0.410135	−0.214909	0.073*
H20B	0.479018	0.406459	−0.146977	0.073*
H20C	0.444898	0.475073	−0.081145	0.073*
C21	0.15861 (4)	0.48931 (11)	0.01536 (15)	0.0236 (3)
H21A	0.171421	0.554309	0.006909	0.028*
H21B	0.151861	0.464552	−0.079645	0.028*
C22	0.18585 (4)	0.21118 (10)	0.36365 (14)	0.0211 (3)
H22A	0.187148	0.144655	0.324899	0.025*
H22B	0.203585	0.213168	0.450330	0.025*
C23	0.08765 (5)	0.54219 (14)	0.0076 (2)	0.0377 (4)
H23A	0.079379	0.499682	−0.071942	0.045*
H23B	0.097029	0.605225	−0.029458	0.045*
C24	0.05040 (6)	0.55790 (16)	0.1017 (2)	0.0463 (5)
H24A	0.027562	0.588779	0.047480	0.069*
H24B	0.058927	0.599810	0.180190	0.069*
H24C	0.041134	0.495061	0.136829	0.069*
C25	0.12618 (5)	0.15790 (12)	0.47949 (17)	0.0310 (3)
H25A	0.144671	0.146157	0.562741	0.037*
H25B	0.124111	0.096805	0.425257	0.037*
C26	0.08382 (6)	0.18715 (17)	0.5240 (2)	0.0510 (5)
H26A	0.065729	0.199860	0.441426	0.076*
H26B	0.086119	0.246069	0.581013	0.076*
H26C	0.071990	0.134609	0.578500	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0200 (5)	0.0328 (6)	0.0319 (6)	0.0042 (4)	0.0009 (4)	0.0053 (4)
O2	0.0232 (5)	0.0280 (5)	0.0286 (5)	0.0012 (4)	0.0092 (4)	0.0056 (4)
C1	0.0207 (6)	0.0205 (6)	0.0191 (6)	−0.0004 (5)	−0.0011 (5)	−0.0030 (5)
C2	0.0186 (6)	0.0229 (7)	0.0186 (6)	−0.0017 (5)	0.0005 (5)	−0.0035 (5)
C3	0.0210 (6)	0.0207 (6)	0.0150 (6)	−0.0024 (5)	0.0010 (5)	−0.0035 (5)
C4	0.0204 (6)	0.0195 (6)	0.0152 (6)	−0.0018 (5)	−0.0014 (5)	−0.0036 (5)
C5	0.0231 (7)	0.0229 (6)	0.0160 (6)	−0.0017 (5)	−0.0012 (5)	−0.0002 (5)
C6	0.0213 (6)	0.0245 (7)	0.0199 (6)	0.0011 (5)	−0.0034 (5)	0.0002 (5)
C7	0.0194 (6)	0.0254 (7)	0.0174 (6)	−0.0019 (5)	−0.0017 (5)	−0.0036 (5)
C8	0.0193 (7)	0.0293 (7)	0.0238 (7)	−0.0002 (5)	−0.0022 (5)	−0.0016 (6)
C9	0.0195 (6)	0.0314 (7)	0.0238 (7)	−0.0043 (6)	0.0010 (5)	−0.0044 (6)
C10	0.0219 (7)	0.0280 (7)	0.0213 (7)	−0.0066 (5)	0.0012 (5)	−0.0003 (5)
C11	0.0215 (7)	0.0234 (7)	0.0173 (6)	−0.0047 (5)	−0.0007 (5)	−0.0030 (5)
C12	0.0239 (7)	0.0250 (7)	0.0199 (6)	−0.0054 (5)	−0.0002 (5)	0.0020 (5)
C13	0.0235 (7)	0.0219 (6)	0.0202 (6)	−0.0014 (5)	−0.0022 (5)	0.0012 (5)
C14	0.0211 (6)	0.0205 (6)	0.0173 (6)	−0.0026 (5)	−0.0012 (5)	−0.0027 (5)
C15	0.0189 (6)	0.0201 (6)	0.0148 (6)	−0.0032 (5)	−0.0012 (5)	−0.0043 (5)
C16	0.0186 (6)	0.0217 (6)	0.0166 (6)	−0.0034 (5)	−0.0014 (5)	−0.0047 (5)
C17	0.0181 (7)	0.0408 (9)	0.0304 (8)	−0.0033 (6)	0.0023 (6)	0.0003 (7)
C18	0.0296 (9)	0.0502 (11)	0.0529 (11)	0.0012 (8)	0.0112 (8)	−0.0052 (9)
C19	0.0233 (8)	0.0935 (17)	0.0408 (10)	−0.0099 (9)	−0.0019 (7)	−0.0037 (10)
C20	0.0279 (9)	0.0553 (12)	0.0643 (13)	−0.0033 (8)	0.0137 (8)	0.0125 (10)
C21	0.0222 (7)	0.0249 (7)	0.0238 (7)	0.0007 (5)	0.0006 (5)	0.0009 (5)
C22	0.0212 (7)	0.0233 (6)	0.0190 (6)	0.0005 (5)	0.0017 (5)	−0.0007 (5)
C23	0.0278 (8)	0.0406 (9)	0.0440 (10)	0.0084 (7)	−0.0060 (7)	0.0047 (7)
C24	0.0290 (9)	0.0485 (11)	0.0613 (13)	0.0075 (8)	−0.0006 (8)	0.0051 (9)
C25	0.0322 (8)	0.0314 (8)	0.0297 (8)	−0.0051 (6)	0.0063 (6)	0.0058 (6)
C26	0.0440 (11)	0.0556 (12)	0.0543 (12)	0.0011 (9)	0.0127 (9)	0.0115 (10)

Geometric parameters (Å, º) top

O1—C21	1.4177 (17)	C14—C15	1.4239 (19)
O1—C23	1.4219 (18)	C15—C16	1.4295 (18)
O2—C22	1.4123 (16)	C17—C18	1.525 (3)
O2—C25	1.4198 (18)	C17—C19	1.525 (2)
C1—C2	1.3912 (19)	C17—C20	1.538 (2)
C1—C14	1.4126 (19)	C18—H18A	0.9600
C1—C21	1.5107 (19)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C2—C3	1.3935 (19)	C19—H19A	0.9600
C3—C4	1.4089 (18)	C19—H19B	0.9600
C3—C22	1.5042 (18)	C19—H19C	0.9600
C4—C5	1.4455 (19)	C20—H20A	0.9600
C4—C15	1.4217 (18)	C20—H20B	0.9600
C5—H5	0.9300	C20—H20C	0.9600
C5—C6	1.3527 (19)	C21—H21A	0.9700
C6—H6	0.9300	C21—H21B	0.9700
C6—C7	1.4321 (19)	C22—H22A	0.9700
C7—C8	1.3998 (19)	C22—H22B	0.9700
C7—C16	1.4201 (19)	C23—H23A	0.9700
C8—H8	0.9300	C23—H23B	0.9700
C8—C9	1.397 (2)	C23—C24	1.517 (3)
C9—C10	1.395 (2)	C24—H24A	0.9600
C9—C17	1.533 (2)	C24—H24B	0.9600
C10—H10	0.9300	C24—H24C	0.9600
C10—C11	1.4021 (19)	C25—H25A	0.9700
C11—C12	1.433 (2)	C25—H25B	0.9700
C11—C16	1.4196 (19)	C25—C26	1.472 (2)
C12—H12	0.9300	C26—H26A	0.9600
C12—C13	1.3550 (19)	C26—H26B	0.9600
C13—H13	0.9300	C26—H26C	0.9600
C13—C14	1.4390 (19)

C21—O1—C23	111.60 (12)	C19—C17—C20	107.14 (15)
C22—O2—C25	110.73 (11)	C17—C18—H18A	109.5
C2—C1—C14	119.64 (12)	C17—C18—H18B	109.5
C2—C1—C21	120.19 (12)	C17—C18—H18C	109.5
C14—C1—C21	120.05 (12)	H18A—C18—H18B	109.5
C1—C2—H2	118.9	H18A—C18—H18C	109.5
C1—C2—C3	122.19 (13)	H18B—C18—H18C	109.5
C3—C2—H2	118.9	C17—C19—H19A	109.5
C2—C3—C4	119.57 (12)	C17—C19—H19B	109.5
C2—C3—C22	120.87 (12)	C17—C19—H19C	109.5
C4—C3—C22	119.52 (12)	H19A—C19—H19B	109.5
C3—C4—C5	122.42 (12)	H19A—C19—H19C	109.5
C3—C4—C15	119.09 (12)	H19B—C19—H19C	109.5
C15—C4—C5	118.48 (12)	C17—C20—H20A	109.5
C4—C5—H5	119.3	C17—C20—H20B	109.5
C6—C5—C4	121.45 (13)	C17—C20—H20C	109.5
C6—C5—H5	119.3	H20A—C20—H20B	109.5
C5—C6—H6	119.3	H20A—C20—H20C	109.5
C5—C6—C7	121.41 (13)	H20B—C20—H20C	109.5
C7—C6—H6	119.3	O1—C21—C1	110.31 (11)
C8—C7—C6	122.16 (13)	O1—C21—H21A	109.6
C8—C7—C16	119.31 (13)	O1—C21—H21B	109.6
C16—C7—C6	118.52 (12)	C1—C21—H21A	109.6
C7—C8—H8	118.8	C1—C21—H21B	109.6
C9—C8—C7	122.39 (13)	H21A—C21—H21B	108.1
C9—C8—H8	118.8	O2—C22—C3	110.80 (11)
C8—C9—C17	119.52 (13)	O2—C22—H22A	109.5
C10—C9—C8	117.68 (13)	O2—C22—H22B	109.5
C10—C9—C17	122.80 (13)	C3—C22—H22A	109.5
C9—C10—H10	118.9	C3—C22—H22B	109.5
C9—C10—C11	122.28 (13)	H22A—C22—H22B	108.1
C11—C10—H10	118.9	O1—C23—H23A	110.1
C10—C11—C12	122.31 (12)	O1—C23—H23B	110.1
C10—C11—C16	119.37 (13)	O1—C23—C24	107.98 (15)
C16—C11—C12	118.32 (12)	H23A—C23—H23B	108.4
C11—C12—H12	119.2	C24—C23—H23A	110.1
C13—C12—C11	121.56 (13)	C24—C23—H23B	110.1
C13—C12—H12	119.2	C23—C24—H24A	109.5
C12—C13—H13	119.3	C23—C24—H24B	109.5
C12—C13—C14	121.50 (13)	C23—C24—H24C	109.5
C14—C13—H13	119.3	H24A—C24—H24B	109.5
C1—C14—C13	122.78 (12)	H24A—C24—H24C	109.5
C1—C14—C15	118.86 (12)	H24B—C24—H24C	109.5
C15—C14—C13	118.35 (12)	O2—C25—H25A	109.6
C4—C15—C14	120.64 (12)	O2—C25—H25B	109.6
C4—C15—C16	119.57 (12)	O2—C25—C26	110.12 (14)
C14—C15—C16	119.77 (12)	H25A—C25—H25B	108.1
C7—C16—C15	120.56 (12)	C26—C25—H25A	109.6
C11—C16—C7	118.94 (12)	C26—C25—H25B	109.6
C11—C16—C15	120.49 (12)	C25—C26—H26A	109.5
C9—C17—C20	112.03 (14)	C25—C26—H26B	109.5
C18—C17—C9	109.20 (13)	C25—C26—H26C	109.5
C18—C17—C20	108.61 (15)	H26A—C26—H26B	109.5
C19—C17—C9	109.68 (13)	H26A—C26—H26C	109.5
C19—C17—C18	110.15 (16)	H26B—C26—H26C	109.5

C1—C2—C3—C4	−0.15 (19)	C9—C10—C11—C12	−179.23 (13)
C1—C2—C3—C22	−178.02 (12)	C9—C10—C11—C16	0.1 (2)
C1—C14—C15—C4	0.52 (19)	C10—C9—C17—C18	−112.72 (17)
C1—C14—C15—C16	179.28 (11)	C10—C9—C17—C19	126.49 (18)
C2—C1—C14—C13	178.77 (12)	C10—C9—C17—C20	7.6 (2)
C2—C1—C14—C15	0.11 (19)	C10—C11—C12—C13	179.79 (13)
C2—C1—C21—O1	18.16 (18)	C10—C11—C16—C7	−0.90 (19)
C2—C3—C4—C5	−178.61 (12)	C10—C11—C16—C15	179.90 (11)
C2—C3—C4—C15	0.78 (18)	C11—C12—C13—C14	0.3 (2)
C2—C3—C22—O2	−7.55 (17)	C12—C11—C16—C7	178.45 (12)
C3—C4—C5—C6	179.82 (12)	C12—C11—C16—C15	−0.76 (19)
C3—C4—C15—C14	−0.97 (18)	C12—C13—C14—C1	−179.53 (13)
C3—C4—C15—C16	−179.72 (11)	C12—C13—C14—C15	−0.9 (2)
C4—C3—C22—O2	174.58 (11)	C13—C14—C15—C4	−178.20 (12)
C4—C5—C6—C7	0.0 (2)	C13—C14—C15—C16	0.55 (18)
C4—C15—C16—C7	−0.18 (18)	C14—C1—C2—C3	−0.3 (2)
C4—C15—C16—C11	179.01 (11)	C14—C1—C21—O1	−165.83 (12)
C5—C4—C15—C14	178.44 (12)	C14—C15—C16—C7	−178.95 (12)
C5—C4—C15—C16	−0.31 (18)	C14—C15—C16—C11	0.24 (19)
C5—C6—C7—C8	−179.81 (13)	C15—C4—C5—C6	0.43 (19)
C5—C6—C7—C16	−0.5 (2)	C16—C7—C8—C9	0.3 (2)
C6—C7—C8—C9	179.60 (13)	C16—C11—C12—C13	0.5 (2)
C6—C7—C16—C11	−178.64 (12)	C17—C9—C10—C11	−179.90 (13)
C6—C7—C16—C15	0.57 (19)	C21—O1—C23—C24	−173.86 (14)
C7—C8—C9—C10	−1.0 (2)	C21—C1—C2—C3	175.73 (12)
C7—C8—C9—C17	179.70 (13)	C21—C1—C14—C13	2.7 (2)
C8—C7—C16—C11	0.73 (19)	C21—C1—C14—C15	−175.92 (12)
C8—C7—C16—C15	179.94 (12)	C22—O2—C25—C26	174.09 (14)
C8—C9—C10—C11	0.9 (2)	C22—C3—C4—C5	−0.71 (19)
C8—C9—C17—C18	66.50 (18)	C22—C3—C4—C15	178.67 (11)
C8—C9—C17—C19	−54.3 (2)	C23—O1—C21—C1	−166.10 (12)
C8—C9—C17—C20	−173.13 (15)	C25—O2—C22—C3	172.25 (11)

Acknowledgements

The authors are grateful to the Center for Instrumental Analysis, Kyushu Institute of Technology (KITCIA), for the X-ray analysis.

References

Bruker (2009). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dötz, F., Brand, J. D., Ito, S., Gherghel, L. & Müllen, K. (2000). J. Am. Chem. Soc. 122, 7707–7717. Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Moriguchi, T., Higashi, M., Yakeya, D., Venkataprasad, J., Tsuge, A., Okauchi, T., Nagamatsu, S. & Takashima, W. (2017). J. Mol. Struct. 1127, 413–418. CrossRef CAS Google Scholar
Moriguchi, T., Kitou, N., Iwamoto, T., Yoza, K. & Tsuge, A. (2015). J. Chem. Res. 39, 351–356. CrossRef CAS Google Scholar
Moriguchi, T., Yakeya, D., Tsuge, A. & Venkataprasad, J. (2018). J. Mol. Struct. 1157, 348–354. CrossRef CAS Google Scholar
Moriguchi, T., Yoza, K. & Tsuge, A. (2014). J. Crystallogr. Article ID 271238. Google Scholar
Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384–7391. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.