Literature DB >> 23723948

3,4,5-Trimeth-oxy-4'-methyl-biphen-yl.

Manu Lahtinen¹, Kalle Nättinen, Sami Nummelin.

Abstract

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

Entities: CellLine Chemical Disease Species

Year: 2013 PMID： 23723948 PMCID： PMC3648328 DOI： 10.1107/S1600536813010969

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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. (2004 ▶); Nummelin et al. (2000 ▶).

Experimental

Crystal data

C16H18O3 M = 258.30 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.117 S = 1.03 2589 reflections 173 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.20 e Å−3 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. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010969/go2088sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010969/go2088Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813010969/go2088Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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 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

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	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)

	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)

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)

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

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) ; (ii) ; (iii) ; (iv) ; (v) .

10 in total

1. Bisfunctionalized Janus molecules.

Authors: Jarmo Ropponen; Sami Nummelin; Kari Rissanen
Journal: Org Lett Date: 2004-07-22 Impact factor: 6.005

2. Self-assembly of Janus dendrimers into uniform dendrimersomes and other complex architectures.

Authors: Virgil Percec; Daniela A Wilson; Pawaret Leowanawat; Christopher J Wilson; Andrew D Hughes; Mark S Kaucher; Daniel A Hammer; Dalia H Levine; Anthony J Kim; Frank S Bates; Kevin P Davis; Timothy P Lodge; Michael L Klein; Russell H DeVane; Emad Aqad; Brad M Rosen; Andreea O Argintaru; Monika J Sienkowska; Kari Rissanen; Sami Nummelin; Jarmo Ropponen
Journal: Science Date: 2010-05-21 Impact factor: 47.728

3. Self-assembly of hybrid dendrons with complex primary structure into functional helical pores.

Authors: Virgil Percec; Jan Smidrkal; Mihai Peterca; Catherine M Mitchell; Sami Nummelin; Andrés E Dulcey; Monika J Sienkowska; Paul A Heiney
Journal: Chemistry Date: 2007 Impact factor: 5.236

4. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

5. Hollow spherical supramolecular dendrimers.

Authors: Virgil Percec; Mihai Peterca; Andrés E Dulcey; Mohammad R Imam; Steven D Hudson; Sami Nummelin; Peter Adelman; Paul A Heiney
Journal: J Am Chem Soc Date: 2008-09-05 Impact factor: 15.419

6. Exploring and expanding the structural diversity of self-assembling dendrons through combinations of AB, constitutional isomeric AB2, and AB3 biphenyl-4-methyl ether building blocks.

Authors: Virgil Percec; Marian N Holerca; Sami Nummelin; John J Morrison; Martin Glodde; Jan Smidrkal; Mihai Peterca; Brad M Rosen; Satoshi Uchida; Venkatachalapathy S K Balagurusamy; Monika J Sienkowska; Paul A Heiney
Journal: Chemistry Date: 2006-08-16 Impact factor: 5.236