Literature DB >> 23476569

Methyl 3',4',5'-trimeth-oxy-biphenyl-4-carboxyl-ate.

Manu Lahtinen¹, Kalle Nättinen, Sami Nummelin.

Abstract

In the title compound, C17H18O5, the dihedral angle between the benzene rings is 31.23 (16)°. In the crystal, the mol-ecules are packed in an anti-parallel fashion in layers along the a axis. In each layer, very weak C-H⋯O hydrogen bonds occur between the meth-oxy and methyl ester groups. Weak C-H⋯π inter-actions between the 4'- and 5'-meth-oxy groups and neighbouring benzene rings [meth-oxy-C-ring centroid distances = 4.075 and 3.486 Å, respectively] connect the layers.

Entities: Chemical Disease Species

Year: 2013 PMID： 23476569 PMCID： PMC3588494 DOI： 10.1107/S1600536813004133

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

Related literature

For a related structure, see: Li et al. (2012 ▶). For the nature of hydrogen bonding, see Steiner (2002 ▶); For related biphenyl structures, see: Leowanawat et al. (2011 ▶); Wilson et al. (2008 ▶); Percec et al. (2004 ▶); Suzuki (1999 ▶). For details of the synthesis and amphiphilic supramolecular biphenyl dendrimers, see: Percec et al. (2006 ▶, 2007 ▶). For general background to self-assembling dendrons and dendrimers, see: Rosen et al. (2009 ▶); For the use of aromatic and aliphatic ester derivatives in the synthesis of dendrimers and dendrons, see Nummelin et al. (2000 ▶); Twibanire & Grindley (2012 ▶).

Experimental

Crystal data

C17H18O5 M = 302.31 Triclinic, a = 7.9103 (5) Å b = 8.6054 (7) Å c = 11.8779 (7) Å α = 92.834 (6)° β = 92.448 (5)° γ = 115.822 (7)° V = 725.07 (9) Å3 Z = 2 Cu Kα radiation μ = 0.84 mm−1 T = 123 K 0.49 × 0.23 × 0.10 mm

Data collection

Agilent SuperNova (Dual source with Cu, Atlas) diffractometer Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) ▶ T min = 0.827, T max = 0.951 4547 measured reflections 2731 independent reflections 2524 reflections with I > 2σ(I) R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.096 S = 1.05 2731 reflections 204 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.25 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); 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/S1600536813004133/fj2614sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004133/fj2614Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813004133/fj2614Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₈O₅	Z = 2
M_r = 302.31	F(000) = 320
Triclinic, P1	D_x = 1.385 Mg m⁻³
a = 7.9103 (5) Å	Cu Kα radiation, λ = 1.5418 Å
b = 8.6054 (7) Å	Cell parameters from 3244 reflections
c = 11.8779 (7) Å	θ = 3.7–76.2°
α = 92.834 (6)°	µ = 0.84 mm⁻¹
β = 92.448 (5)°	T = 123 K
γ = 115.822 (7)°	Plate, colourless
V = 725.07 (9) Å³	0.49 × 0.23 × 0.10 mm

Agilent SuperNova (Dual source with Cu, Atlas) diffractometer	2731 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2524 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.016
Detector resolution: 10.3953 pixels mm^-1	θ_max = 70.0°, θ_min = 3.7°
ω scans	h = −6→9
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −10→10
T_min = 0.827, T_max = 0.951	l = −14→14
4547 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0554P)² + 0.167P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2731 reflections	Δρ_max = 0.26 e Å⁻³
204 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (13)

Experimental. (CrysAlisPro; Agilent 2010)

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
O20	0.15945 (10)	0.37481 (10)	0.32775 (6)	0.0189 (2)
O17	0.09397 (11)	0.16999 (10)	0.13913 (7)	0.0215 (2)
O2	1.52912 (10)	1.04374 (10)	0.31139 (7)	0.0209 (2)
O14	0.37423 (11)	0.19633 (11)	0.00966 (7)	0.0228 (2)
O4	1.43214 (11)	1.16372 (11)	0.45157 (7)	0.0249 (2)
C19	0.31151 (15)	0.40188 (14)	0.26702 (9)	0.0164 (2)
C22	0.49386 (15)	0.52658 (14)	0.29919 (9)	0.0164 (2)
H22	0.5177	0.6002	0.3661	0.020*
C16	0.27386 (15)	0.29495 (14)	0.16769 (9)	0.0174 (2)
C6	1.17401 (15)	0.76841 (15)	0.27483 (9)	0.0185 (2)
H6	1.2780	0.7473	0.2559	0.022*
C7	0.99186 (15)	0.64548 (14)	0.24261 (9)	0.0183 (2)
H7	0.9724	0.5398	0.2030	0.022*
C11	0.64163 (15)	0.54313 (14)	0.23285 (9)	0.0166 (2)
C10	1.05099 (15)	0.95224 (14)	0.36160 (9)	0.0191 (2)
H10	1.0707	1.0566	0.4032	0.023*
C5	1.20468 (15)	0.92276 (14)	0.33487 (9)	0.0168 (2)
C8	0.83642 (15)	0.67484 (14)	0.26762 (9)	0.0164 (2)
C18	0.00490 (16)	0.20396 (16)	0.04195 (11)	0.0254 (3)
H18A	0.0834	0.2196	−0.0221	0.038*
H18B	−0.0109	0.3094	0.0586	0.038*
H18C	−0.1187	0.1061	0.0230	0.038*
C9	0.86947 (15)	0.83046 (14)	0.32792 (10)	0.0190 (2)
H9	0.7660	0.8529	0.3460	0.023*
C3	1.39732 (15)	1.05633 (14)	0.37365 (9)	0.0180 (2)
C13	0.42300 (16)	0.31014 (14)	0.10261 (9)	0.0183 (2)
C15	0.51955 (16)	0.20895 (16)	−0.06177 (10)	0.0235 (3)
H15A	0.4656	0.1228	−0.1263	0.035*
H15B	0.6151	0.1876	−0.0190	0.035*
H15C	0.5778	0.3252	−0.0890	0.035*
C12	0.60543 (15)	0.43431 (14)	0.13456 (9)	0.0181 (2)
H12	0.7057	0.4451	0.0894	0.022*
C21	0.19948 (16)	0.44995 (16)	0.44155 (9)	0.0225 (3)
H21A	0.2520	0.5762	0.4413	0.034*
H21B	0.2908	0.4186	0.4804	0.034*
H21C	0.0831	0.4065	0.4809	0.034*
C1	1.72008 (15)	1.17042 (15)	0.34262 (11)	0.0229 (3)
H1A	1.8043	1.1574	0.2888	0.034*
H1B	1.7580	1.1529	0.4188	0.034*
H1C	1.7275	1.2870	0.3415	0.034*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O20	0.0124 (4)	0.0220 (4)	0.0179 (4)	0.0041 (3)	0.0012 (3)	−0.0038 (3)
O17	0.0139 (4)	0.0212 (4)	0.0202 (4)	−0.0003 (3)	−0.0014 (3)	−0.0019 (3)
O2	0.0114 (4)	0.0209 (4)	0.0239 (4)	0.0017 (3)	0.0009 (3)	−0.0050 (3)
O14	0.0173 (4)	0.0238 (4)	0.0196 (4)	0.0029 (3)	0.0015 (3)	−0.0086 (3)
O4	0.0183 (4)	0.0222 (4)	0.0269 (4)	0.0034 (3)	−0.0004 (3)	−0.0090 (3)
C19	0.0137 (5)	0.0174 (5)	0.0174 (5)	0.0061 (4)	0.0014 (4)	0.0017 (4)
C22	0.0148 (5)	0.0159 (5)	0.0158 (5)	0.0048 (4)	−0.0011 (4)	−0.0018 (4)
C16	0.0125 (5)	0.0158 (5)	0.0185 (5)	0.0016 (4)	−0.0017 (4)	−0.0010 (4)
C6	0.0139 (5)	0.0210 (5)	0.0191 (5)	0.0067 (4)	0.0015 (4)	−0.0018 (4)
C7	0.0160 (5)	0.0177 (5)	0.0180 (5)	0.0052 (4)	0.0000 (4)	−0.0045 (4)
C11	0.0141 (5)	0.0157 (5)	0.0179 (5)	0.0048 (4)	−0.0008 (4)	0.0007 (4)
C10	0.0173 (5)	0.0162 (5)	0.0211 (5)	0.0052 (4)	0.0023 (4)	−0.0022 (4)
C5	0.0141 (5)	0.0174 (5)	0.0150 (5)	0.0035 (4)	0.0004 (4)	0.0004 (4)
C8	0.0148 (5)	0.0167 (5)	0.0146 (5)	0.0040 (4)	0.0005 (4)	0.0005 (4)
C18	0.0174 (5)	0.0251 (6)	0.0294 (6)	0.0066 (5)	−0.0066 (5)	−0.0042 (5)
C9	0.0144 (5)	0.0183 (5)	0.0227 (6)	0.0058 (4)	0.0021 (4)	−0.0011 (4)
C3	0.0160 (5)	0.0175 (5)	0.0184 (5)	0.0056 (4)	0.0011 (4)	0.0004 (4)
C13	0.0185 (5)	0.0178 (5)	0.0158 (5)	0.0059 (4)	−0.0006 (4)	−0.0019 (4)
C15	0.0214 (6)	0.0264 (6)	0.0200 (6)	0.0084 (5)	0.0031 (4)	−0.0054 (5)
C12	0.0143 (5)	0.0193 (5)	0.0183 (5)	0.0055 (4)	0.0013 (4)	−0.0006 (4)
C21	0.0173 (5)	0.0282 (6)	0.0176 (6)	0.0063 (5)	0.0027 (4)	−0.0032 (4)
C1	0.0120 (5)	0.0201 (6)	0.0298 (6)	0.0012 (4)	0.0000 (4)	−0.0011 (5)

O20—C19	1.3667 (13)	C10—H10	0.9500
O20—C21	1.4298 (13)	C10—C5	1.3916 (15)
O17—C16	1.3733 (13)	C10—C9	1.3851 (16)
O17—C18	1.4345 (14)	C5—C3	1.4891 (15)
O2—C3	1.3424 (13)	C8—C9	1.3997 (15)
O2—C1	1.4442 (13)	C18—H18A	0.9800
O14—C13	1.3618 (13)	C18—H18B	0.9800
O14—C15	1.4271 (13)	C18—H18C	0.9800
O4—C3	1.2076 (14)	C9—H9	0.9500
C19—C22	1.3937 (15)	C13—C12	1.3921 (15)
C19—C16	1.3969 (15)	C15—H15A	0.9800
C22—H22	0.9500	C15—H15B	0.9800
C22—C11	1.3972 (15)	C15—H15C	0.9800
C16—C13	1.4000 (16)	C12—H12	0.9500
C6—H6	0.9500	C21—H21A	0.9800
C6—C7	1.3881 (15)	C21—H21B	0.9800
C6—C5	1.3937 (15)	C21—H21C	0.9800
C7—H7	0.9500	C1—H1A	0.9800
C7—C8	1.3994 (15)	C1—H1B	0.9800
C11—C8	1.4857 (14)	C1—H1C	0.9800
C11—C12	1.3971 (15)

C19—O20—C21	116.33 (8)	H18A—C18—H18B	109.5
C16—O17—C18	113.77 (9)	H18A—C18—H18C	109.5
C3—O2—C1	115.40 (8)	H18B—C18—H18C	109.5
C13—O14—C15	117.61 (9)	C10—C9—C8	120.93 (10)
O20—C19—C22	123.79 (10)	C10—C9—H9	119.5
O20—C19—C16	115.53 (9)	C8—C9—H9	119.5
C22—C19—C16	120.67 (10)	O2—C3—C5	111.90 (9)
C19—C22—H22	120.1	O4—C3—O2	123.63 (10)
C19—C22—C11	119.89 (10)	O4—C3—C5	124.47 (10)
C11—C22—H22	120.1	O14—C13—C16	115.08 (10)
O17—C16—C19	119.67 (10)	O14—C13—C12	124.58 (10)
O17—C16—C13	121.07 (10)	C12—C13—C16	120.34 (10)
C19—C16—C13	119.14 (10)	O14—C15—H15A	109.5
C7—C6—H6	119.9	O14—C15—H15B	109.5
C7—C6—C5	120.16 (10)	O14—C15—H15C	109.5
C5—C6—H6	119.9	H15A—C15—H15B	109.5
C6—C7—H7	119.5	H15A—C15—H15C	109.5
C6—C7—C8	121.03 (10)	H15B—C15—H15C	109.5
C8—C7—H7	119.5	C11—C12—H12	119.9
C22—C11—C8	119.97 (10)	C13—C12—C11	120.23 (10)
C12—C11—C22	119.69 (10)	C13—C12—H12	119.9
C12—C11—C8	120.34 (10)	O20—C21—H21A	109.5
C5—C10—H10	119.8	O20—C21—H21B	109.5
C9—C10—H10	119.8	O20—C21—H21C	109.5
C9—C10—C5	120.44 (10)	H21A—C21—H21B	109.5
C6—C5—C3	122.00 (10)	H21A—C21—H21C	109.5
C10—C5—C6	119.29 (10)	H21B—C21—H21C	109.5
C10—C5—C3	118.69 (10)	O2—C1—H1A	109.5
C7—C8—C11	120.91 (10)	O2—C1—H1B	109.5
C7—C8—C9	118.14 (10)	O2—C1—H1C	109.5
C9—C8—C11	120.95 (10)	H1A—C1—H1B	109.5
O17—C18—H18A	109.5	H1A—C1—H1C	109.5
O17—C18—H18B	109.5	H1B—C1—H1C	109.5
O17—C18—H18C	109.5

O20—C19—C22—C11	178.85 (10)	C7—C6—C5—C10	−0.25 (17)
O20—C19—C16—O17	−1.73 (15)	C7—C6—C5—C3	178.45 (10)
O20—C19—C16—C13	−177.75 (10)	C7—C8—C9—C10	0.19 (17)
O17—C16—C13—O14	1.62 (16)	C11—C8—C9—C10	179.15 (10)
O17—C16—C13—C12	−178.14 (10)	C10—C5—C3—O2	−157.96 (10)
O14—C13—C12—C11	−178.77 (10)	C10—C5—C3—O4	21.96 (17)
C19—C22—C11—C8	−179.40 (9)	C5—C6—C7—C8	1.18 (17)
C19—C22—C11—C12	−0.02 (16)	C5—C10—C9—C8	0.72 (17)
C19—C16—C13—O14	177.58 (10)	C8—C11—C12—C13	179.52 (10)
C19—C16—C13—C12	−2.18 (17)	C18—O17—C16—C19	111.07 (11)
C22—C19—C16—O17	178.33 (9)	C18—O17—C16—C13	−72.99 (13)
C22—C19—C16—C13	2.31 (17)	C9—C10—C5—C6	−0.70 (17)
C22—C11—C8—C7	148.15 (11)	C9—C10—C5—C3	−179.43 (10)
C22—C11—C8—C9	−30.78 (15)	C15—O14—C13—C16	178.23 (10)
C22—C11—C12—C13	0.14 (16)	C15—O14—C13—C12	−2.02 (16)
C16—C19—C22—C11	−1.23 (16)	C12—C11—C8—C7	−31.23 (16)
C16—C13—C12—C11	0.97 (17)	C12—C11—C8—C9	149.84 (11)
C6—C7—C8—C11	179.90 (10)	C21—O20—C19—C22	−15.21 (15)
C6—C7—C8—C9	−1.14 (16)	C21—O20—C19—C16	164.86 (10)
C6—C5—C3—O2	23.34 (15)	C1—O2—C3—O4	−0.72 (16)
C6—C5—C3—O4	−156.74 (12)	C1—O2—C3—C5	179.20 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.98	2.58	3.4933 (15)	156
C18—H18C···O14ⁱⁱ	0.98	2.50	3.4453 (16)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.98	2.58	3.4933 (15)	156
C18—H18C⋯O14ⁱⁱ	0.98	2.50	3.4453 (16)	161

Symmetry codes: (i) ; (ii) .

8 in total

1. 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

2. A short history of SHELX.

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

Review 3. Dendron-mediated self-assembly, disassembly, and self-organization of complex systems.

Authors: Brad M Rosen; Christopher J Wilson; Daniela A Wilson; Mihai Peterca; Mohammad R Imam; Virgil Percec
Journal: Chem Rev Date: 2009-11 Impact factor: 60.622

4. Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.

Authors: Pawaret Leowanawat; Na Zhang; Ana-Maria Resmerita; Brad M Rosen; Virgil Percec
Journal: J Org Chem Date: 2011-11-16 Impact factor: 4.354

5. 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

6. Two-step, one-pot Ni-catalyzed neopentylglycolborylation and complementary Pd/Ni-catalyzed cross-coupling with aryl halides, mesylates, and tosylates.

Authors: Daniela A Wilson; Christopher J Wilson; Brad M Rosen; Virgil Percec
Journal: Org Lett Date: 2008-09-26 Impact factor: 6.005

7. NiCl(2)(dppe)-catalyzed cross-coupling of aryl mesylates, arenesulfonates, and halides with arylboronic acids.

Authors: Virgil Percec; Geoffrey M Golding; Jan Smidrkal; Oliver Weichold
Journal: J Org Chem Date: 2004-05-14 Impact factor: 4.354

8. 3,4-Dimeth-oxy-4'-nitro-1,1'-biphen-yl.

Authors: Xin-Min Li; Yan-Jun Hou; Wen-Yi Chu; Zhi-Zhong Sun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-04