3,5-Dimeth­oxy-4′-methyl­biphen­yl

Lahtinen, M.; Nättinen, K.; Nummelin, S.

doi:10.1107/S1600536813006053

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o510-o511

doi:10.1107/S1600536813006053

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3,5-Dimethoxy-4′-methylbiphenyl

Manu Lahtinen,^a Kalle Nättinen ^b and Sami Nummelin ^c ^*

^aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 JY, Finland, ^bVTT Technical Research Centre of Finland, Tampere, FIN-33101, Finland, and ^cMolecular Materials, Department of Applied Physics, School of Science, Aalto University, PO Box 15100, FI-00076 Aalto, Finland
^*Correspondence e-mail: sami.nummelin@aalto.fi

(Received 27 February 2013; accepted 3 March 2013; online 9 March 2013)

The title compound, C₁₅H₁₆O₂, crystallizes with three independent molecules in the asymmetric unit. The intramolecular torsion angle between the aromatic rings of each molecule are −36.4 (3), 41.3 (3) and −37.8 (3)°. In the crystal, the complicated packing of the molecules forms wave-like layers along the b and c axes. The molecules are connected via extensive methoxy–phenyl C—H⋯π interactions. A weak C—H⋯O hydrogen-bonding network also exists between methoxy O atoms and aromatic or methoxy H atoms.

Related literature

For discussion of hydrogen bonding, see: Steiner (2002 ). For similar structures, see: Nakagawa et al. (1984 ); Pandi et al. (2000 ); Lahtinen et al. (2013a ,b ). For details of the synthesis, see: Dol et al. (1998 ); Percec et al. (2006 ). The Suzuki–Miyaura cross-coupling reaction (Miyaura & Suzuki, 1995 ) is widely used for the synthesis of biphenyls and related biaryl structures in organic, polymer, and supramolecular chemistry. Such structures are frequently used as building blocks for e.g. precursors to liquid crystals (Solladié & Zimmermann 1984 ), supramolecular polymers (Brunsveld et al. 2001 ), dendritic molecules (Nummelin et al. 2000 ) as well as Percec-type self-assembling biphenyl dendrons (Percec et al., 2006, 2007 ; Rosen et al., 2009 , 2010 ).

Experimental

Crystal data

C₁₅H₁₆O₂
M_r = 228.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.16505 (18) Å
b = 15.3511 (4) Å
c = 33.3834 (8) Å
V = 3671.88 (16) Å³
Z = 12
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 123 K
0.31 × 0.07 × 0.04 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ) T_min = 0.900, T_max = 0.979
8494 measured reflections
5862 independent reflections
5181 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.094
S = 1.04
5862 reflections
470 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 2062 Friedel pairs
Flack parameter: 0.09 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1–Cg6 are the centroids of C26–C31, C2–C7, C33–C38, C20–C25, C8–C13 and C26–C31 aromatic rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29⋯O15ⁱ	0.95	2.40	3.321 (2)	164
C25—H25⋯O51ⁱⁱ	0.95	2.84	3.459 (3)	124
C24—H24⋯O17ⁱⁱⁱ	0.95	2.91	3.703 (3)	141
C16—H16A⋯O34^iv	0.98	2.68	3.521 (3)	143
C52—H52A⋯O17^v	0.98	2.63	3.398 (3)	136
C18—H18A⋯Cg1ⁱⁱⁱ	0.98	2.89	3.686 (3)	142
C16—H16C⋯Cg2^iv	0.98	2.62	3.366 (3)	139
C33—H33B⋯Cg3ⁱⁱⁱ	0.98	3.05	3.476 (3)	115
C52—H52B⋯Cg4^v	0.98	2.77	3.424 (3)	134
C35—H35C⋯Cg5ⁱⁱⁱ	0.98	2.77	3.639 (3)	146
C35—H35B⋯Cg5	0.98	2.78	3.563 (3)	143
C18—H18C⋯Cg6^vi	0.98	2.75	3.663 (3)	148
Symmetry codes: (i) $[-x-2, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) x+1, y-1, z; (iii) x+1, y, z; (iv) $[-x-2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (v) x, y+1, z; (vi) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006053/fj2619sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006053/fj2619Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006053/fj2619Isup3.cml

checkCIF report

Comment top

The Suzuki-Miyaura cross-coupling reaction (Miyaura & Suzuki 1995) is widely used for the synthesis of biphenyls and related biaryl structures in organic, polymer, and supramolecular chemistry. Such structures are frequently used as building blocks for e.g precursors to liquid crystals (Solladié & Zimmermann 1984), supramolecular polymers (Brunsveld et al. 2001), dendritic molecules (Nummelin et al. 2000), and recently, Percec-type self-assembling supramolecular dendrimers (Percec et al. 2006, 2007; Rosen et al. 2009, 2010). Herein we report the crystal structure of title compound 3,5-dimethoxy-4'-methylbiphenyl (I) as a contribution to a structural study of biphenyl derivatives.

The compound (I) crystallizes in orthorhombic P2₁2₁2₁ (No. 19) spacegroup without any solvent molecules. The asymmetric unit is consisted of three crystallographically independent but conformationally quite similar molecules (Figure 1). Major difference in conformation can be found in the orientation of one of the methoxy groups as can be seen in Figure 2. The intramolecular dihedral angles between the phenyl rings are -36.4 (3)° [C(4)–C(5)–C(8)–C(9)], 41.3 (3)° [C(22)–C(23)–C(26)–C(27)], and -37.8 (3)° [C(39)–C(40)–C(43)–C(44)], respectively. The complicated packing scheme of molecules form wave-like layers (layer on b- and c-axes) that are packed along a-axis (Figure 3). On each wave-like layer, molecules are orientated by 90° turns in a sequence of three crystallographically independent molecules (Figure 4). Extensive network of C–H···π and π–π interactions occur between methoxy groups and neighboring phenyl groups and between the phenyl rings (Figure 5) with distances varying from 3.366 (3) to 3.686 (3) Å and from 4.8418 (11) to 4.9137 (12) Å, respectively (Table 1). Also weak C–H···O hydrogen bond networks (Steiner 2002) exist between the methoxy groups of 3,5-dimethoxyphenyl rings and neighbouring hydrogen atoms located either on methoxy groups or in aromatic rings with D···A distances varying from 3.321 (2) to 3.703 (3) Å.

Related literature top

For discussion of hydrogen bonding, see: Steiner (2002). For similar structures, see: Nakagawa et al. (1984); Pandi et al. (2000); Lahtinen et al. (2013a,b). For details of the synthesis, see: Dol et al. (1998); Percec et al. (2006). The Suzuki–Miyaura cross-coupling reaction (Miyaura & Suzuki, 1995) is widely used for the synthesis of biphenyls and related biaryl structures in organic, polymer, and supramolecular chemistry. Such structures are frequently used as building blocks for e.g. precursors to liquid crystals (Solladié & Zimmermann 1984), supramolecular polymers (Brunsveld et al. 2001), dendritic molecules (Nummelin et al. 2000) as well as Percec-type self-assembling biphenyl dendrons (Percec et al., 2006, 2007; Rosen et al., 2009, 2010).

Experimental top

A flame dried Schlenk-tube was charged with 4-methylphenylboronic acid (6.00 g, 44.13 mmol), potassium fluoride (5.13 g, 88.30 mmol), 1-chloro-3,5-dimethoxybenzene (5.08 g, 29.43 mmol), Pd(OAc)₂ (66 mg, 0.29 mmol, 1.0 mol%) and 2-(di-tert-butylphosphino)biphenyl (176 mg, 0.59 mmol, 2.0 mol%). The flask was sealed with a teflon screwcap, evacuated/backfilled with argon five times. Then dry, degassed THF (40 ml) was added via syringe. The reaction mixture was stirred at ambient temperature until the aryl chloride had been completely consumed as judged by GC analysis. The mixture was diluted with ether, filtered, and washed with 1 M NaOH. The aqueous layer was extracted with ether, the combined organic layer was washed with brine and dried with MgSO₄. After evaporation the crude material was purified by flash column chromatography: silica gel/CH₂Cl₂. The solvent was evaporated and the product was re-crystallized from EtOH affording 6.40 g (95%) of a white crystalline solid. Crystals suitable for a single-crystal structure determination were obtained from a slow evaporation of ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Overlay of three crystallographically disctinct molecules of an asymmetric unit.
	Fig. 3. Packing of molecules along b- and c -axes, showing stacking of wave-like layers of molecules.
	Fig. 4. Packing order of crystallographically independent molecules on a single wave-like layer.
	Fig. 5. Extensive C–H···π and π–π interaction network shown along b-axis.

3,5-Dimethoxy-4'-methylbiphenyl top

Crystal data top

C₁₅H₁₆O₂	D_x = 1.239 Mg m⁻³
M_r = 228.28	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4358 reflections
a = 7.16505 (18) Å	θ = 4.0–76.3°
b = 15.3511 (4) Å	µ = 0.64 mm⁻¹
c = 33.3834 (8) Å	T = 123 K
V = 3671.88 (16) Å³	Rod, colourless
Z = 12	0.31 × 0.07 × 0.04 mm
F(000) = 1464

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	5862 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5181 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 5.1977 pixels mm^-1	θ_max = 68.0°, θ_min = 3.9°
ω scans	h = −8→8
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −12→18
T_min = 0.900, T_max = 0.979	l = −35→40
8494 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0416P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.094	(Δ/σ)_max = 0.004
S = 1.04	Δρ_max = 0.21 e Å⁻³
5862 reflections	Δρ_min = −0.22 e Å⁻³
470 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00022 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2062 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.09 (19)

Crystal data top

C₁₅H₁₆O₂	V = 3671.88 (16) Å³
M_r = 228.28	Z = 12
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 7.16505 (18) Å	µ = 0.64 mm⁻¹
b = 15.3511 (4) Å	T = 123 K
c = 33.3834 (8) Å	0.31 × 0.07 × 0.04 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	5862 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	5181 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.979	R_int = 0.028
8494 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.21 e Å⁻³
S = 1.04	Δρ_min = −0.22 e Å⁻³
5862 reflections	Absolute structure: Flack (1983), 2062 Friedel pairs
470 parameters	Absolute structure parameter: 0.09 (19)
0 restraints

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
O32	−0.6581 (3)	0.00455 (9)	−0.13539 (4)	0.0257 (3)
O15	−1.2140 (2)	−0.53532 (9)	−0.24070 (4)	0.0230 (3)
O17	−1.1815 (3)	−0.31557 (9)	−0.14009 (4)	0.0256 (3)
O34	−0.7204 (2)	−0.24734 (10)	−0.21097 (4)	0.0257 (3)
O51	−1.1549 (3)	0.51057 (9)	−0.07803 (4)	0.0258 (3)
C48	−1.1888 (3)	0.36199 (13)	−0.09024 (6)	0.0203 (4)
H48	−1.2070	0.3761	−0.1177	0.024*
C31	−0.6807 (3)	−0.26527 (13)	−0.13890 (6)	0.0195 (4)
H31	−0.6843	−0.3270	−0.1407	0.023*
O49	−1.1295 (3)	0.30941 (10)	0.03053 (4)	0.0287 (4)
C8	−1.2439 (3)	−0.30112 (13)	−0.24971 (6)	0.0179 (4)
C11	−1.1978 (3)	−0.42464 (13)	−0.18851 (6)	0.0188 (4)
H11	−1.1833	−0.4665	−0.1678	0.023*
C46	−1.1387 (3)	0.40899 (14)	−0.02203 (6)	0.0233 (4)
H46	−1.1189	0.4541	−0.0030	0.028*
C44	−1.1719 (3)	0.25491 (14)	−0.03740 (6)	0.0206 (4)
H44	−1.1763	0.1960	−0.0288	0.025*
C13	−1.2266 (3)	−0.27383 (13)	−0.20985 (6)	0.0187 (4)
H13	−1.2312	−0.2136	−0.2035	0.022*
C23	−0.6510 (3)	−0.27891 (13)	−0.06500 (6)	0.0196 (4)
C45	−1.1468 (3)	0.32131 (15)	−0.00984 (6)	0.0224 (4)
C35	−0.7262 (4)	−0.34030 (14)	−0.21533 (6)	0.0276 (5)
H35A	−0.7526	−0.3551	−0.2433	0.041*
H35B	−0.8245	−0.3642	−0.1981	0.041*
H35C	−0.6055	−0.3651	−0.2075	0.041*
C10	−1.2146 (3)	−0.45040 (13)	−0.22815 (6)	0.0191 (4)
C30	−0.6954 (3)	−0.21431 (14)	−0.17353 (6)	0.0207 (4)
C28	−0.6658 (3)	−0.08472 (13)	−0.13408 (6)	0.0211 (4)
C36	−1.2425 (4)	−0.00048 (14)	−0.19728 (7)	0.0307 (5)
H36A	−1.1237	−0.0051	−0.2117	0.046*
H36B	−1.3426	0.0127	−0.2163	0.046*
H36C	−1.2694	−0.0558	−0.1838	0.046*
C2	−1.2986 (3)	−0.10882 (13)	−0.34317 (6)	0.0221 (4)
C5	−1.2669 (3)	−0.23535 (12)	−0.28198 (6)	0.0174 (4)
C43	−1.1908 (3)	0.27539 (14)	−0.07817 (6)	0.0201 (4)
C26	−0.6609 (3)	−0.22480 (13)	−0.10173 (6)	0.0200 (4)
C27	−0.6522 (3)	−0.13359 (13)	−0.09919 (6)	0.0203 (4)
H27	−0.6371	−0.1057	−0.0740	0.024*
C9	−1.2396 (3)	−0.38929 (13)	−0.25875 (6)	0.0197 (4)
H9	−1.2536	−0.4081	−0.2857	0.024*
C38	−1.1136 (3)	0.06328 (14)	−0.13330 (6)	0.0239 (5)
H38	−1.0395	0.0124	−0.1303	0.029*
C29	−0.6881 (3)	−0.12423 (14)	−0.17108 (6)	0.0223 (4)
H29	−0.6983	−0.0898	−0.1946	0.027*
C39	−1.1042 (3)	0.12794 (14)	−0.10462 (6)	0.0208 (4)
H39	−1.0263	0.1200	−0.0819	0.025*
C21	−0.7427 (3)	−0.30780 (14)	0.00358 (6)	0.0235 (4)
H21	−0.8070	−0.2896	0.0270	0.028*
C6	−1.3671 (3)	−0.15842 (13)	−0.27573 (6)	0.0201 (4)
H6	−1.4261	−0.1485	−0.2507	0.024*
C3	−1.2022 (3)	−0.18594 (13)	−0.34947 (6)	0.0206 (4)
H3	−1.1473	−0.1965	−0.3749	0.025*
C25	−0.5491 (3)	−0.40961 (14)	−0.03083 (7)	0.0236 (5)
H25	−0.4799	−0.4624	−0.0312	0.028*
C24	−0.5494 (3)	−0.35747 (13)	−0.06463 (6)	0.0204 (4)
H24	−0.4809	−0.3747	−0.0877	0.025*
C40	−1.2074 (3)	0.20496 (13)	−0.10848 (6)	0.0194 (4)
C4	−1.1841 (3)	−0.24814 (13)	−0.31951 (6)	0.0197 (4)
H4	−1.1148	−0.2998	−0.3245	0.024*
C50	−1.1437 (4)	0.22174 (15)	0.04516 (6)	0.0280 (5)
H50A	−1.0489	0.1854	0.0321	0.042*
H50B	−1.2681	0.1987	0.0391	0.042*
H50C	−1.1237	0.2212	0.0742	0.042*
C20	−0.6471 (3)	−0.38717 (14)	0.00367 (6)	0.0246 (4)
C41	−1.3212 (3)	0.21389 (13)	−0.14206 (6)	0.0207 (4)
H41	−1.3919	0.2657	−0.1455	0.025*
C22	−0.7454 (3)	−0.25507 (14)	−0.03023 (6)	0.0236 (5)
H22	−0.8129	−0.2018	−0.0296	0.028*
C47	−1.1602 (3)	0.42827 (14)	−0.06234 (6)	0.0214 (4)
C18	−1.1755 (4)	−0.22542 (13)	−0.12935 (6)	0.0248 (5)
H18A	−1.0726	−0.1969	−0.1436	0.037*
H18B	−1.1563	−0.2200	−0.1004	0.037*
H18C	−1.2937	−0.1976	−0.1368	0.037*
C12	−1.2028 (3)	−0.33505 (13)	−0.17976 (6)	0.0193 (4)
C37	−1.2300 (3)	0.07136 (13)	−0.16657 (6)	0.0212 (4)
C42	−1.3328 (3)	0.14800 (14)	−0.17063 (6)	0.0227 (4)
H42	−1.4120	0.1554	−0.1932	0.027*
C16	−1.1429 (3)	−0.59988 (13)	−0.21377 (6)	0.0249 (5)
H16A	−1.1382	−0.6564	−0.2274	0.037*
H16B	−1.2248	−0.6041	−0.1903	0.037*
H16C	−1.0170	−0.5834	−0.2051	0.037*
C33	−0.6269 (4)	0.05009 (13)	−0.09882 (7)	0.0270 (5)
H33A	−0.6359	0.1129	−0.1036	0.041*
H33B	−0.5023	0.0360	−0.0886	0.041*
H33C	−0.7211	0.0326	−0.0791	0.041*
C7	−1.3810 (3)	−0.09623 (14)	−0.30590 (7)	0.0236 (5)
H7	−1.4483	−0.0440	−0.3009	0.028*
C52	−1.0702 (4)	0.57706 (15)	−0.05435 (7)	0.0284 (5)
H52A	−1.0571	0.6302	−0.0704	0.043*
H52B	−0.9467	0.5576	−0.0455	0.043*
H52C	−1.1485	0.5891	−0.0309	0.043*
C1	−1.3141 (4)	−0.04042 (15)	−0.37556 (7)	0.0313 (5)
H1A	−1.2136	0.0023	−0.3724	0.047*
H1B	−1.4350	−0.0110	−0.3734	0.047*
H1C	−1.3036	−0.0682	−0.4019	0.047*
C19	−0.6454 (4)	−0.44453 (18)	0.04011 (7)	0.0378 (6)
H19A	−0.5222	−0.4419	0.0528	0.057*
H19B	−0.6724	−0.5047	0.0322	0.057*
H19C	−0.7405	−0.4244	0.0591	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O32	0.0337 (9)	0.0178 (7)	0.0256 (7)	−0.0004 (7)	−0.0006 (7)	−0.0008 (6)
O15	0.0326 (9)	0.0153 (6)	0.0210 (7)	0.0011 (7)	−0.0057 (6)	0.0012 (5)
O17	0.0373 (9)	0.0223 (7)	0.0172 (6)	0.0002 (7)	−0.0014 (7)	−0.0015 (6)
O34	0.0337 (9)	0.0237 (7)	0.0197 (7)	−0.0028 (7)	−0.0015 (7)	−0.0025 (6)
O51	0.0322 (9)	0.0180 (7)	0.0273 (7)	−0.0013 (7)	−0.0057 (7)	−0.0014 (6)
C48	0.0191 (10)	0.0235 (10)	0.0185 (9)	0.0014 (9)	0.0003 (8)	−0.0002 (8)
C31	0.0174 (10)	0.0167 (8)	0.0244 (9)	0.0024 (8)	0.0015 (8)	−0.0010 (8)
O49	0.0370 (10)	0.0308 (8)	0.0184 (7)	0.0024 (8)	−0.0023 (7)	−0.0006 (6)
C8	0.0128 (9)	0.0209 (9)	0.0200 (9)	0.0006 (8)	0.0017 (8)	0.0015 (8)
C11	0.0159 (10)	0.0195 (9)	0.0210 (9)	−0.0010 (8)	−0.0006 (8)	0.0039 (8)
C46	0.0215 (11)	0.0249 (10)	0.0234 (10)	0.0008 (9)	−0.0015 (9)	−0.0046 (8)
C44	0.0179 (10)	0.0234 (10)	0.0204 (10)	−0.0006 (8)	0.0013 (8)	0.0024 (8)
C13	0.0187 (10)	0.0164 (9)	0.0211 (9)	−0.0010 (8)	0.0019 (8)	−0.0009 (8)
C23	0.0171 (10)	0.0193 (9)	0.0224 (9)	−0.0008 (9)	0.0000 (8)	−0.0021 (8)
C45	0.0179 (10)	0.0319 (11)	0.0174 (9)	−0.0003 (9)	−0.0002 (8)	−0.0013 (9)
C35	0.0298 (12)	0.0283 (11)	0.0246 (10)	−0.0031 (10)	0.0030 (9)	−0.0075 (9)
C10	0.0162 (10)	0.0165 (9)	0.0246 (10)	−0.0004 (8)	−0.0019 (8)	0.0003 (8)
C30	0.0174 (10)	0.0249 (10)	0.0196 (9)	0.0004 (9)	0.0014 (8)	−0.0017 (8)
C28	0.0162 (10)	0.0196 (9)	0.0276 (10)	0.0003 (8)	0.0017 (9)	−0.0001 (8)
C36	0.0411 (15)	0.0238 (10)	0.0272 (11)	−0.0018 (11)	0.0023 (10)	−0.0035 (9)
C2	0.0215 (11)	0.0207 (10)	0.0240 (9)	−0.0045 (9)	−0.0022 (9)	0.0031 (8)
C5	0.0169 (10)	0.0155 (8)	0.0200 (9)	−0.0021 (8)	−0.0011 (8)	−0.0003 (8)
C43	0.0173 (9)	0.0238 (10)	0.0193 (9)	0.0014 (9)	0.0013 (8)	−0.0002 (8)
C26	0.0163 (10)	0.0214 (9)	0.0223 (9)	0.0017 (9)	0.0020 (8)	−0.0003 (8)
C27	0.0199 (10)	0.0216 (10)	0.0194 (9)	−0.0016 (9)	0.0014 (8)	−0.0032 (8)
C9	0.0227 (10)	0.0214 (9)	0.0148 (8)	−0.0005 (9)	−0.0010 (8)	−0.0006 (8)
C38	0.0263 (11)	0.0183 (9)	0.0271 (11)	0.0018 (9)	0.0039 (9)	0.0021 (9)
C29	0.0193 (10)	0.0253 (10)	0.0223 (9)	0.0025 (9)	0.0015 (9)	0.0024 (8)
C39	0.0217 (11)	0.0215 (10)	0.0192 (9)	0.0014 (9)	−0.0008 (8)	0.0031 (8)
C21	0.0234 (11)	0.0271 (10)	0.0199 (9)	0.0019 (9)	0.0026 (8)	−0.0035 (8)
C6	0.0198 (10)	0.0198 (9)	0.0206 (9)	−0.0005 (9)	0.0017 (8)	−0.0009 (8)
C3	0.0214 (11)	0.0237 (10)	0.0168 (9)	−0.0026 (9)	−0.0009 (8)	0.0006 (8)
C25	0.0248 (11)	0.0194 (10)	0.0267 (11)	0.0021 (9)	−0.0041 (9)	−0.0018 (9)
C24	0.0197 (10)	0.0192 (10)	0.0224 (10)	−0.0006 (9)	0.0012 (8)	−0.0035 (8)
C40	0.0209 (10)	0.0186 (9)	0.0188 (9)	−0.0012 (8)	0.0043 (8)	0.0025 (8)
C4	0.0206 (10)	0.0182 (9)	0.0203 (9)	0.0018 (8)	−0.0011 (8)	−0.0005 (7)
C50	0.0285 (12)	0.0354 (12)	0.0202 (9)	−0.0014 (11)	−0.0021 (9)	0.0042 (9)
C20	0.0233 (11)	0.0262 (10)	0.0243 (10)	−0.0050 (10)	−0.0044 (9)	0.0027 (9)
C41	0.0214 (10)	0.0185 (9)	0.0223 (9)	0.0001 (8)	0.0025 (8)	0.0013 (8)
C22	0.0262 (12)	0.0224 (10)	0.0223 (10)	0.0028 (9)	0.0003 (9)	−0.0025 (8)
C47	0.0171 (10)	0.0211 (9)	0.0261 (10)	0.0015 (9)	0.0016 (9)	0.0004 (8)
C18	0.0307 (12)	0.0222 (10)	0.0214 (9)	0.0003 (10)	0.0015 (9)	−0.0042 (8)
C12	0.0159 (9)	0.0235 (10)	0.0186 (9)	−0.0034 (8)	0.0007 (8)	−0.0017 (8)
C37	0.0217 (11)	0.0195 (9)	0.0223 (10)	−0.0034 (9)	0.0043 (8)	0.0006 (8)
C42	0.0236 (11)	0.0266 (10)	0.0178 (9)	−0.0034 (9)	−0.0012 (9)	−0.0002 (8)
C16	0.0279 (12)	0.0158 (9)	0.0311 (11)	0.0018 (9)	−0.0089 (10)	0.0044 (8)
C33	0.0321 (13)	0.0186 (9)	0.0304 (11)	−0.0005 (9)	0.0027 (10)	−0.0024 (9)
C7	0.0230 (11)	0.0188 (9)	0.0292 (11)	0.0045 (9)	0.0002 (9)	−0.0001 (9)
C52	0.0297 (12)	0.0204 (10)	0.0351 (12)	−0.0008 (10)	−0.0064 (10)	−0.0031 (9)
C1	0.0345 (13)	0.0281 (11)	0.0313 (11)	−0.0005 (11)	−0.0011 (10)	0.0086 (10)
C19	0.0400 (15)	0.0429 (14)	0.0306 (12)	0.0002 (13)	0.0005 (12)	0.0098 (11)

Geometric parameters (Å, º) top

O32—C28	1.372 (3)	C43—C40	1.486 (3)
O32—C33	1.424 (3)	C26—C27	1.404 (3)
O15—C10	1.369 (2)	C27—H27	0.9500
O15—C16	1.432 (2)	C9—H9	0.9500
O17—C18	1.430 (2)	C38—H38	0.9500
O17—C12	1.366 (2)	C38—C39	1.381 (3)
O34—C35	1.435 (3)	C38—C37	1.394 (3)
O34—C30	1.361 (3)	C29—H29	0.9500
O51—C47	1.368 (3)	C39—H39	0.9500
O51—C52	1.427 (3)	C39—C40	1.400 (3)
C48—H48	0.9500	C21—H21	0.9500
C48—C43	1.389 (3)	C21—C20	1.398 (3)
C48—C47	1.394 (3)	C21—C22	1.389 (3)
C31—H31	0.9500	C6—H6	0.9500
C31—C30	1.400 (3)	C6—C7	1.391 (3)
C31—C26	1.395 (3)	C3—H3	0.9500
O49—C45	1.366 (3)	C3—C4	1.389 (3)
O49—C50	1.435 (3)	C25—H25	0.9500
C8—C13	1.401 (3)	C25—C24	1.383 (3)
C8—C5	1.486 (3)	C25—C20	1.392 (3)
C8—C9	1.387 (3)	C24—H24	0.9500
C11—H11	0.9500	C40—C41	1.393 (3)
C11—C10	1.386 (3)	C4—H4	0.9500
C11—C12	1.406 (3)	C50—H50A	0.9800
C46—H46	0.9500	C50—H50B	0.9800
C46—C45	1.407 (3)	C50—H50C	0.9800
C46—C47	1.387 (3)	C20—C19	1.502 (3)
C44—H44	0.9500	C41—H41	0.9500
C44—C45	1.385 (3)	C41—C42	1.393 (3)
C44—C43	1.403 (3)	C22—H22	0.9500
C13—H13	0.9500	C18—H18A	0.9800
C13—C12	1.386 (3)	C18—H18B	0.9800
C23—C26	1.483 (3)	C18—H18C	0.9800
C23—C24	1.409 (3)	C37—C42	1.395 (3)
C23—C22	1.392 (3)	C42—H42	0.9500
C35—H35A	0.9800	C16—H16A	0.9800
C35—H35B	0.9800	C16—H16B	0.9800
C35—H35C	0.9800	C16—H16C	0.9800
C10—C9	1.398 (3)	C33—H33A	0.9800
C30—C29	1.386 (3)	C33—H33B	0.9800
C28—C27	1.389 (3)	C33—H33C	0.9800
C28—C29	1.385 (3)	C7—H7	0.9500
C36—H36A	0.9800	C52—H52A	0.9800
C36—H36B	0.9800	C52—H52B	0.9800
C36—H36C	0.9800	C52—H52C	0.9800
C36—C37	1.508 (3)	C1—H1A	0.9800
C2—C3	1.386 (3)	C1—H1B	0.9800
C2—C7	1.391 (3)	C1—H1C	0.9800
C2—C1	1.511 (3)	C19—H19A	0.9800
C5—C6	1.397 (3)	C19—H19B	0.9800
C5—C4	1.400 (3)	C19—H19C	0.9800

C28—O32—C33	117.98 (16)	C5—C6—H6	119.7
C10—O15—C16	117.92 (16)	C7—C6—C5	120.57 (19)
C12—O17—C18	117.26 (16)	C7—C6—H6	119.7
C30—O34—C35	117.86 (17)	C2—C3—H3	119.2
C47—O51—C52	117.42 (17)	C2—C3—C4	121.64 (19)
C43—C48—H48	119.8	C4—C3—H3	119.2
C43—C48—C47	120.40 (18)	C24—C25—H25	119.0
C47—C48—H48	119.8	C24—C25—C20	122.1 (2)
C30—C31—H31	120.2	C20—C25—H25	119.0
C26—C31—H31	120.2	C23—C24—H24	119.9
C26—C31—C30	119.57 (18)	C25—C24—C23	120.2 (2)
C45—O49—C50	117.04 (17)	C25—C24—H24	119.9
C13—C8—C5	119.70 (18)	C39—C40—C43	120.62 (19)
C9—C8—C13	119.78 (18)	C41—C40—C43	121.57 (19)
C9—C8—C5	120.53 (18)	C41—C40—C39	117.79 (18)
C10—C11—H11	120.8	C5—C4—H4	119.7
C10—C11—C12	118.35 (18)	C3—C4—C5	120.54 (19)
C12—C11—H11	120.8	C3—C4—H4	119.7
C45—C46—H46	120.7	O49—C50—H50A	109.5
C47—C46—H46	120.7	O49—C50—H50B	109.5
C47—C46—C45	118.7 (2)	O49—C50—H50C	109.5
C45—C44—H44	120.3	H50A—C50—H50B	109.5
C45—C44—C43	119.47 (19)	H50A—C50—H50C	109.5
C43—C44—H44	120.3	H50B—C50—H50C	109.5
C8—C13—H13	120.1	C21—C20—C19	121.1 (2)
C12—C13—C8	119.77 (18)	C25—C20—C21	117.45 (19)
C12—C13—H13	120.1	C25—C20—C19	121.4 (2)
C24—C23—C26	120.77 (18)	C40—C41—H41	119.5
C22—C23—C26	121.26 (19)	C42—C41—C40	120.98 (19)
C22—C23—C24	117.94 (19)	C42—C41—H41	119.5
O49—C45—C46	114.17 (19)	C23—C22—H22	119.4
O49—C45—C44	124.7 (2)	C21—C22—C23	121.2 (2)
C44—C45—C46	121.15 (19)	C21—C22—H22	119.4
O34—C35—H35A	109.5	O51—C47—C48	114.98 (18)
O34—C35—H35B	109.5	O51—C47—C46	124.4 (2)
O34—C35—H35C	109.5	C46—C47—C48	120.6 (2)
H35A—C35—H35B	109.5	O17—C18—H18A	109.5
H35A—C35—H35C	109.5	O17—C18—H18B	109.5
H35B—C35—H35C	109.5	O17—C18—H18C	109.5
O15—C10—C11	124.29 (18)	H18A—C18—H18B	109.5
O15—C10—C9	114.56 (18)	H18A—C18—H18C	109.5
C11—C10—C9	121.13 (18)	H18B—C18—H18C	109.5
O34—C30—C31	124.08 (19)	O17—C12—C11	114.36 (18)
O34—C30—C29	115.53 (19)	O17—C12—C13	124.59 (18)
C29—C30—C31	120.4 (2)	C13—C12—C11	121.05 (18)
O32—C28—C27	124.28 (19)	C38—C37—C36	120.8 (2)
O32—C28—C29	114.43 (19)	C38—C37—C42	117.93 (19)
C29—C28—C27	121.29 (18)	C42—C37—C36	121.3 (2)
H36A—C36—H36B	109.5	C41—C42—C37	121.0 (2)
H36A—C36—H36C	109.5	C41—C42—H42	119.5
H36B—C36—H36C	109.5	C37—C42—H42	119.5
C37—C36—H36A	109.5	O15—C16—H16A	109.5
C37—C36—H36B	109.5	O15—C16—H16B	109.5
C37—C36—H36C	109.5	O15—C16—H16C	109.5
C3—C2—C7	117.76 (19)	H16A—C16—H16B	109.5
C3—C2—C1	121.4 (2)	H16A—C16—H16C	109.5
C7—C2—C1	120.8 (2)	H16B—C16—H16C	109.5
C6—C5—C8	121.55 (18)	O32—C33—H33A	109.5
C6—C5—C4	118.02 (18)	O32—C33—H33B	109.5
C4—C5—C8	120.41 (18)	O32—C33—H33C	109.5
C48—C43—C44	119.65 (19)	H33A—C33—H33B	109.5
C48—C43—C40	119.98 (18)	H33A—C33—H33C	109.5
C44—C43—C40	120.35 (19)	H33B—C33—H33C	109.5
C31—C26—C23	119.41 (18)	C2—C7—C6	121.5 (2)
C31—C26—C27	120.16 (19)	C2—C7—H7	119.3
C27—C26—C23	120.43 (18)	C6—C7—H7	119.3
C28—C27—C26	119.00 (19)	O51—C52—H52A	109.5
C28—C27—H27	120.5	O51—C52—H52B	109.5
C26—C27—H27	120.5	O51—C52—H52C	109.5
C8—C9—C10	119.91 (18)	H52A—C52—H52B	109.5
C8—C9—H9	120.0	H52A—C52—H52C	109.5
C10—C9—H9	120.0	H52B—C52—H52C	109.5
C39—C38—H38	119.4	C2—C1—H1A	109.5
C39—C38—C37	121.2 (2)	C2—C1—H1B	109.5
C37—C38—H38	119.4	C2—C1—H1C	109.5
C30—C29—H29	120.2	H1A—C1—H1B	109.5
C28—C29—C30	119.6 (2)	H1A—C1—H1C	109.5
C28—C29—H29	120.2	H1B—C1—H1C	109.5
C38—C39—H39	119.4	C20—C19—H19A	109.5
C38—C39—C40	121.1 (2)	C20—C19—H19B	109.5
C40—C39—H39	119.4	C20—C19—H19C	109.5
C20—C21—H21	119.4	H19A—C19—H19B	109.5
C22—C21—H21	119.4	H19A—C19—H19C	109.5
C22—C21—C20	121.1 (2)	H19B—C19—H19C	109.5

O32—C28—C27—C26	−179.7 (2)	C9—C8—C5—C6	145.2 (2)
O32—C28—C29—C30	179.2 (2)	C9—C8—C5—C4	−36.4 (3)
O15—C10—C9—C8	179.6 (2)	C38—C39—C40—C43	−177.8 (2)
O34—C30—C29—C28	179.04 (19)	C38—C39—C40—C41	0.5 (3)
C48—C43—C40—C39	140.4 (2)	C38—C37—C42—C41	−0.7 (3)
C48—C43—C40—C41	−37.8 (3)	C29—C28—C27—C26	0.1 (3)
C31—C30—C29—C28	0.1 (4)	C39—C38—C37—C36	−178.6 (2)
C31—C26—C27—C28	0.8 (3)	C39—C38—C37—C42	1.8 (3)
C8—C13—C12—O17	178.9 (2)	C39—C40—C41—C42	0.5 (3)
C8—C13—C12—C11	−0.8 (3)	C6—C5—C4—C3	−0.2 (3)
C8—C5—C6—C7	177.6 (2)	C3—C2—C7—C6	0.3 (3)
C8—C5—C4—C3	−178.69 (19)	C24—C23—C26—C31	40.2 (3)
C11—C10—C9—C8	1.4 (3)	C24—C23—C26—C27	−140.4 (2)
C44—C43—C40—C39	−37.8 (3)	C24—C23—C22—C21	−1.2 (3)
C44—C43—C40—C41	144.0 (2)	C24—C25—C20—C21	−1.9 (3)
C13—C8—C5—C6	−34.7 (3)	C24—C25—C20—C19	180.0 (2)
C13—C8—C5—C4	143.7 (2)	C40—C41—C42—C37	−0.4 (3)
C13—C8—C9—C10	−1.2 (3)	C4—C5—C6—C7	−0.9 (3)
C23—C26—C27—C28	−178.7 (2)	C50—O49—C45—C46	177.7 (2)
C45—C46—C47—O51	−179.9 (2)	C50—O49—C45—C44	−1.8 (3)
C45—C46—C47—C48	−0.2 (4)	C20—C21—C22—C23	−0.8 (4)
C45—C44—C43—C48	−1.6 (3)	C20—C25—C24—C23	−0.1 (3)
C45—C44—C43—C40	176.6 (2)	C22—C23—C26—C31	−138.1 (2)
C35—O34—C30—C31	−2.1 (3)	C22—C23—C26—C27	41.3 (3)
C35—O34—C30—C29	179.1 (2)	C22—C23—C24—C25	1.7 (3)
C10—C11—C12—O17	−178.73 (18)	C22—C21—C20—C25	2.4 (3)
C10—C11—C12—C13	0.9 (3)	C22—C21—C20—C19	−179.5 (2)
C30—C31—C26—C23	178.2 (2)	C47—C48—C43—C44	2.7 (3)
C30—C31—C26—C27	−1.2 (3)	C47—C48—C43—C40	−175.5 (2)
C36—C37—C42—C41	179.7 (2)	C47—C46—C45—O49	−178.2 (2)
C2—C3—C4—C5	1.4 (3)	C47—C46—C45—C44	1.3 (4)
C5—C8—C13—C12	−179.2 (2)	C18—O17—C12—C11	176.9 (2)
C5—C8—C9—C10	178.9 (2)	C18—O17—C12—C13	−2.8 (3)
C5—C6—C7—C2	0.8 (3)	C12—C11—C10—O15	−179.3 (2)
C43—C48—C47—O51	177.9 (2)	C12—C11—C10—C9	−1.2 (3)
C43—C48—C47—C46	−1.8 (3)	C37—C38—C39—C40	−1.7 (3)
C43—C44—C45—O49	179.0 (2)	C16—O15—C10—C11	−17.5 (3)
C43—C44—C45—C46	−0.4 (3)	C16—O15—C10—C9	164.4 (2)
C43—C40—C41—C42	178.8 (2)	C33—O32—C28—C27	2.6 (3)
C26—C31—C30—O34	−178.0 (2)	C33—O32—C28—C29	−177.2 (2)
C26—C31—C30—C29	0.8 (3)	C7—C2—C3—C4	−1.4 (3)
C26—C23—C24—C25	−176.7 (2)	C52—O51—C47—C48	−160.9 (2)
C26—C23—C22—C21	177.1 (2)	C52—O51—C47—C46	18.8 (3)
C27—C28—C29—C30	−0.6 (3)	C1—C2—C3—C4	178.5 (2)
C9—C8—C13—C12	0.9 (3)	C1—C2—C7—C6	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg1–Cg6 are the centroids of C26–C31, C2–C7, C33–C38, C20–C25, C8–C13 and C26–C31 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29···O15ⁱ	0.95	2.40	3.321 (2)	164
C25—H25···O51ⁱⁱ	0.95	2.84	3.459 (3)	124
C24—H24···O17ⁱⁱⁱ	0.95	2.91	3.703 (3)	141
C16—H16A···O34^iv	0.98	2.68	3.521 (3)	143
C52—H52A···O17^v	0.98	2.63	3.398 (3)	136
C18—H18A···Cg1ⁱⁱⁱ	0.98	2.89	3.686 (3)	142
C16—H16C···Cg2^iv	0.98	2.62	3.366 (3)	139
C33—H33B···Cg3ⁱⁱⁱ	0.98	3.05	3.476 (3)	115
C52—H52B···Cg4^v	0.98	2.77	3.424 (3)	134
C35—H35C···Cg5ⁱⁱⁱ	0.98	2.77	3.639 (3)	146
C35—H35B···Cg5	0.98	2.78	3.563 (3)	143
C18—H18C···Cg6^vi	0.98	2.75	3.663 (3)	148

Symmetry codes: (i) −x−2, y+1/2, −z−1/2; (ii) x+1, y−1, z; (iii) x+1, y, z; (iv) −x−2, y−1/2, −z−1/2; (v) x, y+1, z; (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆O₂
M_r	228.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	123
a, b, c (Å)	7.16505 (18), 15.3511 (4), 33.3834 (8)
V (Å³)	3671.88 (16)
Z	12
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.31 × 0.07 × 0.04

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.900, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	8494, 5862, 5181
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.094, 1.04
No. of reflections	5862
No. of parameters	470
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22
Absolute structure	Flack (1983), 2062 Friedel pairs
Absolute structure parameter	0.09 (19)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

Cg1–Cg6 are the centroids of C26–C31, C2–C7, C33–C38, C20–C25, C8–C13 and C26–C31 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29···O15ⁱ	0.95	2.40	3.321 (2)	164
C25—H25···O51ⁱⁱ	0.95	2.84	3.459 (3)	124
C24—H24···O17ⁱⁱⁱ	0.95	2.91	3.703 (3)	141
C16—H16A···O34^iv	0.98	2.68	3.521 (3)	143
C52—H52A···O17^v	0.98	2.63	3.398 (3)	136
C18—H18A···Cg1ⁱⁱⁱ	0.98	2.89	3.686 (3)	142
C16—H16C···Cg2^iv	0.98	2.62	3.366 (3)	139
C33—H33B···Cg3ⁱⁱⁱ	0.98	3.05	3.476 (3)	115
C52—H52B···Cg4^v	0.98	2.77	3.424 (3)	134
C35—H35C···Cg5ⁱⁱⁱ	0.98	2.77	3.639 (3)	146
C35—H35B···Cg5	0.98	2.78	3.563 (3)	143
C18—H18C···Cg6^vi	0.98	2.75	3.663 (3)	148

Symmetry codes: (i) −x−2, y+1/2, −z−1/2; (ii) x+1, y−1, z; (iii) x+1, y, z; (iv) −x−2, y−1/2, −z−1/2; (v) x, y+1, z; (vi) x−1, y, z.

Acknowledgements

SN acknowledges the Academy of Finland for financial support (No. 138850).

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Volume 69| Part 4| April 2013| Pages o510-o511

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