3,4,5-Trimeth­oxy-4′-methyl­biphen­yl

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

doi:10.1107/S1600536813010969

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages o810-o811

https://doi.org/10.1107/S1600536813010969

Open

access

3,4,5-Trimethoxy-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 22 April 2013; accepted 23 April 2013; online 30 April 2013)

In the title compound, C₁₆H₁₈O₃, the dihedral angle between the benzene rings is 33.4 (2)°. In the crystal, molecules are packed in a zigzag arrangement along the b-axis and are interconnected via weak C—H⋯O hydrogen bonds, and C—H⋯π interactions involving the methoxy groups and the benzene rings of neighbouring molecules.

Related literature

For related single-crystal structures based on AB₂– and AB₃-branched biphenyls, see: Lahtinen et al. (2013a ,b ,c ); Lahtinen & Nummelin (2013 ). For synthesis of the title compound, see: Percec et al. (2006 , 2007 ). For crystal structures of dendrimers, see: Mekelburger et al. (1993 ); Nättinen & Rissanen (2003 ); Ropponen et al. (2004a ). For related Percec-type self-assembling supramolecular dendrimers, see: Percec et al. (2006, 2007, 2008 ); Roche & Percec (2013 ). For dendrimersomes, see: Percec et al. (2010 ). For aliphatic and aromatic polyester building blocks for dendrimersomes, see: Ropponen et al. (2004b ,c ); Nummelin et al. (2000 ).

Experimental

Crystal data

C₁₆H₁₈O₃
M_r = 258.30
Orthorhombic, P b c a
a = 8.4669 (2) Å
b = 15.0636 (3) Å
c = 21.4516 (4) Å
V = 2735.98 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.3 × 0.25 × 0.2 mm

Data collection

Bruker–Nonius KappaCCD diffractometer equipped with an APEXII detector
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.983
17856 measured reflections
2589 independent reflections
1984 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.03
2589 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C10/C13/C16/C19 aromatic rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O11ⁱ	0.95	2.57	3.382 (2)	144
C12—H12B⋯O14ⁱ	0.98	2.56	3.465 (2)	154
C18—H18C⋯O17ⁱⁱ	0.98	2.63	3.488 (2)	146
C15—H15A⋯Cg1ⁱⁱⁱ	0.98	2.84	3.692 (2)	139
C12—H12A⋯Cg2^iv	0.98	3.19	4.061 (2)	132
C18—H18B⋯Cg1^v	0.98	3.01	3.976 (2)	149
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (v) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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: https://doi.org/10.1107/S1600536813010969/go2088sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010969/go2088Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010969/go2088Isup3.cml

checkCIF report

Comment top

3,4,5-Trimethoxy-4'-methyl biphenyl was synthesized in a gram quantities by employing a metal catalyzed coupling reaction between an aryl bromide and p-tolylboronic acid (Percec et al. 2006, 2007). The title compound (I) was used as a building block for the construction of amphiphilic AB₂– and AB₃-branched biphenyl dendrons (Percec et al. 2006) and hybrid (phenyl–biphenyl) dendrons (Percec et al. 2007). With few exceptions (e.g. Mekelburger et al. 1993; Nättinen & Rissanen 2003; Ropponen et al. 2004a) most dendrimers are liquid or amorphous. However, Percec-type dendrons and dendrimers have the ability to self-assemble in the solid state and in selected solvents into supramolecular architectures, such as hollow or non-hollow columns or spheres, which, in turn, self-organize into periodic lattices or quasi-periodic arrays in the solid state (Percec et al. 2006, 2007, 2008). In addition, biphenyls (Percec et al. 2006, 2007) are key building blocks on expanding the scope of libraries of amphiphilic Janus-dendrimers (Ropponen et al. 2004b; Percec et al. 2010) based on hydrophobic Percec-type building blocks and hydrophilic aliphatic and aromatic polyester building blocks. (Ropponen et al. 2004b,c; Nummelin et al. 2000). Amphiphilic Janus-dendrimers self-assemble into uniform liposome-like structures denoted as dendrimersomes (Percec et al. 2010) and other complex adaptable systems (Roche & Percec 2013) in water and selected biological buffers. Herein, we report the title compound 3,4,5-trimethoxy-4'-methyl biphenyl (I) as a contribution to a structural study of biphenyl derivatives (Lahtinen et al. 2013a,b,c; Lahtinen & Nummelin 2013).

Compound (I) has a dihedral angle between the aromatic rings of 33.4 (2)°, and is analogous to various biphenyl structures (Lahtinen et al. 2103a,b). The methoxy groups in 3- and 5-positions (Fig. 1) are co-planar with the [C(8)>C(19)] ring with the dihedral angles of 0.2 (2)° and 0.7 (2)°, respectively, whereas the methoxy group in the 4-position is tilted out from the plane with angle 113.32 (13)°. The molecules are packed in a zigzag formation along b -axis. This formation origates from antiparallel rows of molecules running through c -axis (Figures 2 and 3). Three weak CH···O hydrogen bonds occur with donor-acceptor d(D···A) bond distances of 3.382 (2), 3.465 (2), and 3.488 (2) Å, respectively (Fig. 4). Moreover, a network of weak CH···π interactions is observable between methoxy groups and nearby phenyl groups having ring-centroid to methyl(C) distances of 3.692 (2) - 4.061 (2)Å.

Related literature top

For related single-crystal structures based on AB₂– and AB₃-branched biphenyls, see: Lahtinen et al. (2013a,b,c); Lahtinen & Nummelin (2013). For synthesis of the title compound, see Percec et al. (2006, 2007). For selected and sparse examples on single-crystal structures of dendrimers, see Mekelburger et al. (1993); Nättinen & Rissanen (2003); Ropponen et al. (2004a). For related Percec-type self-assembling supramolecular dendrimers, see: Percec et al. (2006, 2007, 2008); Roche & Percec (2013). For dendrimersomes, see Percec et al. (2010). For aliphatic and aromatic polyester building blocks for dendrimersomes, see Ropponen et al. (2004b,c); Nummelin et al. (2000).

Experimental top

A flame-dried Schlenk-tube was loaded with p-tolylboronic acid (3.3 g, 24.3 mmol), KF (2.8 g, 48.6 mmol), 3,4,5-trimethoxy bromobenzene (4.0 g, 16.2 mmol), Pd(OAc)₂ (36 mg, 0.16 mmol, 1.0 mol%) and 2-(di-tert-butylphosphino)biphenyl (97 mg, 0.33 mmol, 2.0 mol%). The tube was sealed with a teflon screwcap and evacuated/backfilled with argon (5x). Then dry, degassed THF (30 ml) was added via syringe and the reaction mixture was stirred at RT until the aryl bromide had been completely consumed as judged by TLC analysis. The mixture was diluted with ether, filtered, and washed with 1M NaOH. The aqueous layer was extracted with ether, the combined organic layer was washed with brine and dried with MgSO₄. After evaporation the pale yellow solid was chromatographed on silica gel using dichloromethane as eluent. Recrystallization from ethanol gave 3.9 g (93%) of the title compound (I) as a white crystalline solid. Crystals suitable for a single-crystal structure determination were obtained from a slow evaporation of the solvent.

Structure description top

For related single-crystal structures based on AB₂– and AB₃-branched biphenyls, see: Lahtinen et al. (2013a,b,c); Lahtinen & Nummelin (2013). For synthesis of the title compound, see Percec et al. (2006, 2007). For selected and sparse examples on single-crystal structures of dendrimers, see Mekelburger et al. (1993); Nättinen & Rissanen (2003); Ropponen et al. (2004a). For related Percec-type self-assembling supramolecular dendrimers, see: Percec et al. (2006, 2007, 2008); Roche & Percec (2013). For dendrimersomes, see Percec et al. (2010). For aliphatic and aromatic polyester building blocks for dendrimersomes, see Ropponen et al. (2004b,c); Nummelin et al. (2000).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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 and atomic numbering of the title compound showing 50% probability displacement ellipsoids.
	Fig. 2. Antiparallel rows of molecules viewed along a-axis.
	Fig. 3. The zigzag arrangement of the molecules viewed along c-axis.
	Fig. 4. CH···O and CH···π interactions shown by blue and black contact lines, respectively.

3,4,5-Trimethoxy-4'-methylbiphenyl top

Crystal data top

C₁₆H₁₈O₃	D_x = 1.254 Mg m⁻³
M_r = 258.30	Mo Kα radiation, λ = 0.71069 Å
Orthorhombic, Pbca	Cell parameters from 9816 reflections
a = 8.4669 (2) Å	θ = 2.9–25.7°
b = 15.0636 (3) Å	µ = 0.09 mm⁻¹
c = 21.4516 (4) Å	T = 173 K
V = 2735.98 (10) Å³	Plate, colourless
Z = 8	0.3 × 0.25 × 0.2 mm
F(000) = 1104

Data collection top

Bruker–Nonius KappaCCD diffractometer equipped with an APEXII detector	2589 independent reflections
Radiation source: sealed tube	1984 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 8 pixels mm^-1	θ_max = 25.7°, θ_min = 2.9°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→18
T_min = 0.975, T_max = 0.983	l = −25→26
17856 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0571P)² + 1.2608P] where P = (F_o² + 2F_c²)/3
2589 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³
0 constraints

Crystal data top

C₁₆H₁₈O₃	V = 2735.98 (10) Å³
M_r = 258.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.4669 (2) Å	µ = 0.09 mm⁻¹
b = 15.0636 (3) Å	T = 173 K
c = 21.4516 (4) Å	0.3 × 0.25 × 0.2 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer equipped with an APEXII detector	2589 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1984 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.052
17856 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
2589 reflections	Δρ_min = −0.20 e Å⁻³
173 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
C1	−0.5594 (2)	−0.00288 (14)	0.14685 (10)	0.0423 (5)
H1A	−0.6400	0.0432	0.1521	0.063*
H1B	−0.5619	−0.0432	0.1827	0.063*
H1C	−0.5807	−0.0364	0.1086	0.063*
C2	−0.3984 (2)	0.03996 (12)	0.14242 (9)	0.0324 (4)
C3	−0.3444 (2)	0.07517 (12)	0.08647 (9)	0.0333 (4)
H3	−0.4095	0.0715	0.0505	0.040*
C4	−0.1974 (2)	0.11563 (11)	0.08190 (8)	0.0305 (4)
H4	−0.1630	0.1387	0.0430	0.037*
C5	−0.10199 (19)	0.12239 (10)	0.13322 (7)	0.0230 (4)
C6	−0.1534 (2)	0.08818 (12)	0.18971 (8)	0.0284 (4)
H6	−0.0881	0.0929	0.2256	0.034*
C7	−0.2995 (2)	0.04713 (11)	0.19405 (8)	0.0311 (4)
H7	−0.3327	0.0235	0.2329	0.037*
C8	0.0553 (2)	0.17020 (11)	0.12955 (8)	0.0245 (4)
C9	0.1441 (2)	0.16780 (11)	0.07478 (7)	0.0248 (4)
H9	0.1084	0.1337	0.0403	0.030*
C10	0.28466 (19)	0.21507 (11)	0.07052 (7)	0.0229 (4)
C12	0.3296 (2)	0.16804 (13)	−0.03432 (8)	0.0356 (5)
H12A	0.4071	0.1748	−0.0679	0.053*
H12B	0.2268	0.1904	−0.0483	0.053*
H12C	0.3201	0.1052	−0.0232	0.053*
C13	0.33806 (19)	0.26545 (11)	0.12094 (7)	0.0233 (4)
C15	0.4574 (2)	0.40464 (12)	0.10715 (9)	0.0347 (4)
H15A	0.5609	0.4335	0.1040	0.052*
H15B	0.3993	0.4294	0.1426	0.052*
H15C	0.3977	0.4150	0.0687	0.052*
C16	0.2514 (2)	0.26602 (11)	0.17617 (7)	0.0244 (4)
C18	0.2258 (2)	0.31828 (12)	0.28086 (7)	0.0294 (4)
H18A	0.2816	0.3556	0.3112	0.044*
H18B	0.2148	0.2581	0.2976	0.044*
H18C	0.1209	0.3433	0.2728	0.044*
C19	0.1099 (2)	0.21951 (11)	0.18045 (8)	0.0251 (4)
H19	0.0502	0.2212	0.2179	0.030*
O11	0.38021 (14)	0.21736 (8)	0.01893 (5)	0.0286 (3)
O14	0.47847 (13)	0.31138 (8)	0.11607 (5)	0.0270 (3)
O17	0.31410 (14)	0.31530 (8)	0.22369 (5)	0.0309 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0279 (10)	0.0437 (12)	0.0554 (13)	−0.0092 (9)	0.0020 (9)	−0.0026 (10)
C2	0.0239 (9)	0.0260 (9)	0.0473 (11)	−0.0003 (8)	0.0001 (8)	−0.0004 (8)
C3	0.0298 (10)	0.0290 (10)	0.0413 (10)	−0.0032 (8)	−0.0080 (8)	0.0006 (8)
C4	0.0309 (10)	0.0260 (9)	0.0347 (9)	−0.0022 (8)	0.0003 (8)	0.0020 (8)
C5	0.0222 (9)	0.0167 (8)	0.0302 (8)	0.0055 (7)	0.0031 (7)	0.0009 (6)
C6	0.0242 (9)	0.0265 (9)	0.0346 (9)	−0.0002 (7)	−0.0020 (7)	−0.0013 (7)
C7	0.0294 (10)	0.0273 (10)	0.0366 (10)	−0.0011 (8)	0.0050 (8)	0.0009 (8)
C8	0.0201 (9)	0.0225 (8)	0.0307 (9)	0.0008 (7)	−0.0023 (7)	0.0020 (7)
C9	0.0251 (9)	0.0242 (9)	0.0252 (8)	−0.0010 (7)	−0.0038 (7)	−0.0020 (7)
C10	0.0218 (9)	0.0241 (9)	0.0229 (8)	0.0025 (7)	0.0009 (6)	0.0027 (6)
C12	0.0410 (11)	0.0395 (11)	0.0262 (9)	−0.0062 (9)	0.0034 (8)	−0.0062 (8)
C13	0.0173 (8)	0.0243 (9)	0.0283 (9)	0.0003 (7)	−0.0006 (6)	0.0013 (7)
C15	0.0336 (11)	0.0278 (10)	0.0426 (11)	−0.0050 (8)	0.0047 (9)	−0.0012 (8)
C16	0.0213 (8)	0.0259 (9)	0.0259 (8)	0.0011 (7)	−0.0029 (7)	−0.0034 (7)
C18	0.0287 (10)	0.0335 (10)	0.0259 (9)	−0.0017 (8)	0.0027 (7)	−0.0037 (7)
C19	0.0219 (9)	0.0272 (9)	0.0261 (9)	0.0001 (7)	0.0018 (7)	0.0002 (7)
O11	0.0276 (7)	0.0353 (7)	0.0229 (6)	−0.0037 (5)	0.0021 (5)	−0.0031 (5)
O14	0.0191 (6)	0.0283 (7)	0.0335 (7)	−0.0037 (5)	0.0015 (5)	−0.0025 (5)
O17	0.0247 (6)	0.0421 (8)	0.0259 (6)	−0.0074 (6)	0.0028 (5)	−0.0094 (5)

Geometric parameters (Å, º) top

C1—H1A	0.9800	C10—C13	1.396 (2)
C1—H1B	0.9800	C10—O11	1.3713 (19)
C1—H1C	0.9800	C12—H12A	0.9800
C1—C2	1.511 (3)	C12—H12B	0.9800
C2—C3	1.389 (3)	C12—H12C	0.9800
C2—C7	1.393 (3)	C12—O11	1.429 (2)
C3—H3	0.9500	C13—C16	1.394 (2)
C3—C4	1.389 (3)	C13—O14	1.3795 (19)
C4—H4	0.9500	C15—H15A	0.9800
C4—C5	1.370 (2)	C15—H15B	0.9800
C5—C6	1.387 (2)	C15—H15C	0.9800
C5—C8	1.516 (2)	C15—O14	1.429 (2)
C6—H6	0.9500	C16—C19	1.391 (2)
C6—C7	1.386 (3)	C16—O17	1.3683 (19)
C7—H7	0.9500	C18—H18A	0.9800
C8—C9	1.396 (2)	C18—H18B	0.9800
C8—C19	1.399 (2)	C18—H18C	0.9800
C9—H9	0.9500	C18—O17	1.4370 (19)
C9—C10	1.389 (2)	C19—H19	0.9500

H1A—C1—H1B	109.5	O11—C10—C13	114.86 (14)
H1A—C1—H1C	109.5	H12A—C12—H12B	109.5
H1B—C1—H1C	109.5	H12A—C12—H12C	109.5
C2—C1—H1A	109.5	H12B—C12—H12C	109.5
C2—C1—H1B	109.5	O11—C12—H12A	109.5
C2—C1—H1C	109.5	O11—C12—H12B	109.5
C3—C2—C1	120.94 (17)	O11—C12—H12C	109.5
C3—C2—C7	117.35 (16)	C16—C13—C10	119.42 (15)
C7—C2—C1	121.70 (17)	O14—C13—C10	119.53 (14)
C2—C3—H3	119.2	O14—C13—C16	121.01 (14)
C4—C3—C2	121.55 (17)	H15A—C15—H15B	109.5
C4—C3—H3	119.2	H15A—C15—H15C	109.5
C3—C4—H4	119.9	H15B—C15—H15C	109.5
C5—C4—C3	120.30 (17)	O14—C15—H15A	109.5
C5—C4—H4	119.9	O14—C15—H15B	109.5
C4—C5—C6	119.32 (16)	O14—C15—H15C	109.5
C4—C5—C8	120.80 (15)	C19—C16—C13	120.44 (15)
C6—C5—C8	119.83 (15)	O17—C16—C13	115.61 (15)
C5—C6—H6	119.9	O17—C16—C19	123.95 (15)
C7—C6—C5	120.29 (16)	H18A—C18—H18B	109.5
C7—C6—H6	119.9	H18A—C18—H18C	109.5
C2—C7—H7	119.4	H18B—C18—H18C	109.5
C6—C7—C2	121.19 (17)	O17—C18—H18A	109.5
C6—C7—H7	119.4	O17—C18—H18B	109.5
C9—C8—C5	120.31 (14)	O17—C18—H18C	109.5
C9—C8—C19	119.55 (15)	C8—C19—H19	120.0
C19—C8—C5	120.11 (15)	C16—C19—C8	120.02 (15)
C8—C9—H9	119.9	C16—C19—H19	120.0
C10—C9—C8	120.22 (15)	C10—O11—C12	117.08 (13)
C10—C9—H9	119.9	C13—O14—C15	113.32 (13)
C9—C10—C13	120.32 (15)	C16—O17—C18	116.80 (13)
O11—C10—C9	124.82 (14)

C1—C2—C3—C4	179.25 (17)	C9—C8—C19—C16	0.3 (2)
C1—C2—C7—C6	−178.67 (17)	C9—C10—C13—C16	1.7 (2)
C2—C3—C4—C5	−0.5 (3)	C9—C10—C13—O14	179.48 (14)
C3—C2—C7—C6	0.3 (3)	C9—C10—O11—C12	0.7 (2)
C3—C4—C5—C6	0.2 (3)	C10—C13—C16—C19	−2.3 (2)
C3—C4—C5—C8	−177.12 (16)	C10—C13—C16—O17	178.43 (15)
C4—C5—C6—C7	0.4 (3)	C10—C13—O14—C15	104.14 (17)
C4—C5—C8—C9	−33.4 (2)	C13—C10—O11—C12	−179.01 (15)
C4—C5—C8—C19	144.48 (17)	C13—C16—C19—C8	1.4 (3)
C5—C6—C7—C2	−0.6 (3)	C13—C16—O17—C18	178.99 (15)
C5—C8—C9—C10	176.97 (15)	C16—C13—O14—C15	−78.13 (19)
C5—C8—C19—C16	−177.60 (15)	C19—C8—C9—C10	−0.9 (2)
C6—C5—C8—C9	149.32 (16)	C19—C16—O17—C18	−0.2 (2)
C6—C5—C8—C19	−32.8 (2)	O11—C10—C13—C16	−178.55 (14)
C7—C2—C3—C4	0.3 (3)	O11—C10—C13—O14	−0.8 (2)
C8—C5—C6—C7	177.71 (15)	O14—C13—C16—C19	179.92 (15)
C8—C9—C10—C13	−0.1 (2)	O14—C13—C16—O17	0.7 (2)
C8—C9—C10—O11	−179.81 (15)	O17—C16—C19—C8	−179.47 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C10/C13/C16/C19 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O11ⁱ	0.95	2.57	3.382 (2)	144
C12—H12B···O14ⁱ	0.98	2.56	3.465 (2)	154
C18—H18C···O17ⁱⁱ	0.98	2.63	3.488 (2)	146
C15—H15A···Cg1ⁱⁱⁱ	0.98	2.84	3.692 (2)	139
C12—H12A···Cg2^iv	0.98	3.19	4.061 (2)	132
C18—H18B···Cg1^v	0.98	3.01	3.976 (2)	149

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x−1/2, y, −z+1/2; (iii) x−1/2, −y+3/2, −z+1; (iv) x+1/2, −y+1/2, −z; (v) −x+3/2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈O₃
M_r	258.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	8.4669 (2), 15.0636 (3), 21.4516 (4)
V (Å³)	2735.98 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.25 × 0.2

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer equipped with an APEXII detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	17856, 2589, 1984
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.03
No. of reflections	2589
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), 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 and Cg2 are the centroids of the C2–C7 and C8–C10/C13/C16/C19 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O11ⁱ	0.95	2.57	3.382 (2)	143.8
C12—H12B···O14ⁱ	0.98	2.56	3.465 (2)	154.3
C18—H18C···O17ⁱⁱ	0.98	2.63	3.488 (2)	145.9
C15—H15A···Cg1ⁱⁱⁱ	0.98	2.84	3.692 (2)	138.8
C12—H12A···Cg2^iv	0.98	3.19	4.061 (2)	131.7
C18—H18B···Cg1^v	0.98	3.01	3.976 (2)	149.1

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x−1/2, y, −z+1/2; (iii) x−1/2, −y+3/2, −z+1; (iv) x+1/2, −y+1/2, −z; (v) −x+3/2, −y+1, z−1/2.

Acknowledgements

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

References

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
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013a). Acta Cryst. E69, o383. CSD CrossRef IUCr Journals Google Scholar
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013b). Acta Cryst. E69, o460. CSD CrossRef IUCr Journals Google Scholar
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013c). Acta Cryst. E69, o510–o511. CSD CrossRef CAS IUCr Journals Google Scholar
Lahtinen, M. & Nummelin, S. (2013). Acta Cryst. E69, o681. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mekelburger, H.-B., Rissanen, K. & Vögtle, F. (1993). Chem. Ber. 126, 1161–1169. CrossRef CAS Web of Science Google Scholar
Nättinen, K. & Rissanen, K. (2003). Cryst. Growth Des. 3, 339–353. Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1–67. CrossRef CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Percec, V., Holerca, M. N., Nummelin, S., Morrison, J. J., Glodde, M., Smidrkal, J., Peterca, M., Uchida, S., Balagurusamy, V. S. K., Sienkowska, M. J. & Heiney, P. A. (2006). Chem. Eur. J. 12, 6216–6241. Web of Science CrossRef PubMed CAS Google Scholar
Percec, V., Peterca, M., Dulcey, A. E., Imam, M. R., Hudson, S. D., Nummelin, S., Adelman, P. & Heiney, P. A. (2008). J. Am. Chem. Soc. 130, 13079–13094. Web of Science CrossRef PubMed CAS Google Scholar
Percec, V., Smidrkal, J., Peterca, M., Mitchell, C. M., Nummelin, S., Dulcey, A. E., Sienkowska, M. J. & Heiney, P. A. (2007). Chem. Eur. J. 13, 3989–4007. Web of Science CrossRef PubMed CAS Google Scholar
Percec, V., Wilson, D. A., Leowanawat, P., Wilson, C. J., Hughes, A. D., Kaucher, M. S., Hammer, D. A., Levine, D. H., Kim, A. J., Bates, F. S., Davis, K. P., Lodge, T. P., Klein, M. L., DeVane, R. H., Aqad, E., Rosen, B. R., Argintaru, A. O., Sienkowska, M. J., Rissanen, K., Nummelin, S. & Ropponen, J. (2010). Science, 328, 1009–1014. Web of Science CrossRef CAS PubMed Google Scholar
Roche, C. & Percec, V. (2013). Isr. J. Chem. 53, 30–44. Web of Science CrossRef CAS Google Scholar
Ropponen, J., Nättinen, K., Lahtinen, M. & Rissanen, K. (2004a). CrystEngComm, 6, 559–566. Web of Science CSD CrossRef CAS Google Scholar
Ropponen, J., Nummelin, S. & Rissanen, K. (2004b). Org. Lett. 6, 2495–2497. Web of Science CrossRef PubMed CAS Google Scholar
Ropponen, J., Tuuttila, T., Lahtinen, M., Nummelin, S. & Rissanen, K. (2004c). J. Polym. Sci. Part A Polym. Chem. 42, 5574–5586. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages o810-o811

https://doi.org/10.1107/S1600536813010969

Open

access