Literature DB >> 23476626

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

Manu Lahtinen¹, Kalle Nättinen, Sami Nummelin.

Abstract

In the title compound, C16H16O4, the dihedral angle between the benzene rings is 28.9 (2)°. In the crystal, mol-ecules are packed in layers parallel to the b axis in which they are connected via weak inter-molecular C-H⋯O contacts. Face-to-face π-π inter-actions also exist between the benzene rings of adjacent mol-ecules, with centroid-centroid and plane-to-plane shift distances of 3.8597 (14) and 1.843 (2) Å, respectively.

Entities: Chemical Disease Gene Species

Year: 2013 PMID： 23476626 PMCID： PMC3588445 DOI： 10.1107/S1600536813005333

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

Related literature

For related structures, see: Lahtinen et al. (2013 ▶); Van Eerdenbrugh et al. (2010 ▶). For the nature of hydrogen bonding, see: Steiner (2002 ▶). For synthesis details and related supramolecular structures based on biphenyls, see: Percec et al. (2006 ▶, 2007 ▶). For related synthetic biphenyl structures, see: Rosen et al. (2008 ▶); Percec et al. (2004 ▶); Wolfe et al. (1999 ▶). For polyester functionalized dendrons and dendrimers, see: Nummelin et al. (2000 ▶). For a general review on self-assembling dendrons and dendrimers, see: Rosen et al. (2009 ▶).

Experimental

Crystal data

C16H16O4 M = 272.29 Triclinic, a = 6.0990 (9) Å b = 7.1622 (16) Å c = 16.2408 (18) Å α = 96.589 (14)° β = 91.472 (11)° γ = 112.493 (18)° V = 649.27 (19) Å3 Z = 2 Cu Kα radiation μ = 0.82 mm−1 T = 123 K 0.29 × 0.19 × 0.04 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer Absorption correction: analytical CrysAlis PRO; Agilent, 2010 ▶) T min = 0.924, T max = 0.983 3989 measured reflections 2395 independent reflections 2025 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.111 S = 1.05 2395 reflections 184 parameters H-atom parameters constrained Δρmax = 0.19 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/S1600536813005333/fj2616sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005333/fj2616Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813005333/fj2616Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₆O₄	Z = 2
M_r = 272.29	F(000) = 288
Triclinic, P1	D_x = 1.393 Mg m⁻³
a = 6.0990 (9) Å	Cu Kα radiation, λ = 1.5418 Å
b = 7.1622 (16) Å	Cell parameters from 2092 reflections
c = 16.2408 (18) Å	θ = 5.5–76.0°
α = 96.589 (14)°	µ = 0.82 mm⁻¹
β = 91.472 (11)°	T = 123 K
γ = 112.493 (18)°	Plate, colourless
V = 649.27 (19) Å³	0.29 × 0.19 × 0.04 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2395 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2025 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.025
Detector resolution: 10.3953 pixels mm^-1	θ_max = 69.0°, θ_min = 5.5°
ω scans	h = −5→7
Absorption correction: analytical CrysAlis PRO; Agilent, 2010)	k = −8→8
T_min = 0.924, T_max = 0.983	l = −19→19
3989 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0591P)² + 0.1033P] where P = (F_o² + 2F_c²)/3
2395 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

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
O4	0.72065 (19)	0.88715 (17)	1.15112 (6)	0.0256 (3)
O2	1.01438 (18)	0.78669 (16)	1.11239 (6)	0.0245 (3)
O18	0.46733 (19)	0.23876 (16)	0.56673 (6)	0.0256 (3)
O14	0.1145 (2)	0.71333 (18)	0.59191 (7)	0.0301 (3)
C3	0.8129 (3)	0.8161 (2)	1.09788 (9)	0.0205 (3)
C6	0.5135 (3)	0.7715 (2)	0.98314 (9)	0.0210 (3)
H6	0.4281	0.8202	1.0223	0.025*
C17	0.4269 (3)	0.3845 (2)	0.61901 (9)	0.0213 (3)
C13	0.2432 (3)	0.6276 (2)	0.63282 (9)	0.0220 (3)
C7	0.4295 (3)	0.7185 (2)	0.89982 (9)	0.0212 (3)
H7	0.2877	0.7335	0.8827	0.025*
C11	0.4573 (2)	0.5869 (2)	0.75182 (9)	0.0201 (3)
C5	0.7225 (3)	0.7530 (2)	1.00911 (9)	0.0202 (3)
C12	0.3244 (3)	0.6839 (2)	0.71684 (9)	0.0214 (3)
H12	0.2899	0.7865	0.7497	0.026*
C16	0.2934 (3)	0.4787 (2)	0.58389 (9)	0.0226 (3)
H16	0.2370	0.4417	0.5269	0.027*
C8	0.5486 (2)	0.6439 (2)	0.84072 (9)	0.0196 (3)
C9	0.7577 (3)	0.6253 (2)	0.86810 (9)	0.0223 (3)
H9	0.8427	0.5753	0.8292	0.027*
C20	0.5067 (3)	0.4362 (2)	0.70285 (9)	0.0211 (3)
H20	0.5948	0.3689	0.7268	0.025*
C10	0.8431 (3)	0.6785 (2)	0.95095 (9)	0.0222 (3)
H10	0.9851	0.6639	0.9682	0.027*
C1	1.1197 (3)	0.8460 (2)	1.19672 (9)	0.0255 (3)
H1A	1.2785	0.8419	1.1987	0.038*
H1B	1.0194	0.7518	1.2325	0.038*
H1C	1.1328	0.9848	1.2163	0.038*
C19	0.6415 (3)	0.1676 (3)	0.59536 (10)	0.0271 (3)
H19A	0.6742	0.0828	0.5495	0.041*
H19B	0.5810	0.0866	0.6406	0.041*
H19C	0.7884	0.2845	0.6156	0.041*
C15	0.0299 (3)	0.8481 (3)	0.64007 (10)	0.0279 (4)
H15A	−0.0638	0.8943	0.6035	0.042*
H15B	0.1656	0.9662	0.6678	0.042*
H15C	−0.0700	0.7764	0.6820	0.042*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0290 (6)	0.0305 (6)	0.0189 (5)	0.0141 (5)	0.0027 (4)	−0.0002 (4)
O2	0.0254 (6)	0.0301 (6)	0.0191 (5)	0.0135 (5)	−0.0029 (4)	−0.0018 (4)
O18	0.0309 (6)	0.0269 (6)	0.0208 (5)	0.0150 (5)	−0.0011 (4)	−0.0025 (4)
O14	0.0377 (6)	0.0365 (6)	0.0232 (6)	0.0235 (5)	−0.0032 (5)	0.0010 (5)
C3	0.0208 (7)	0.0181 (7)	0.0214 (7)	0.0059 (6)	0.0011 (6)	0.0039 (6)
C6	0.0231 (7)	0.0198 (7)	0.0201 (7)	0.0084 (6)	0.0038 (6)	0.0012 (6)
C17	0.0219 (7)	0.0198 (7)	0.0201 (7)	0.0064 (6)	0.0033 (6)	0.0008 (6)
C13	0.0217 (7)	0.0231 (8)	0.0218 (7)	0.0087 (6)	0.0004 (6)	0.0051 (6)
C7	0.0213 (7)	0.0232 (8)	0.0199 (7)	0.0094 (6)	0.0013 (6)	0.0036 (6)
C11	0.0181 (7)	0.0202 (7)	0.0194 (7)	0.0044 (6)	0.0026 (6)	0.0034 (6)
C5	0.0221 (7)	0.0182 (7)	0.0187 (7)	0.0060 (6)	0.0019 (6)	0.0029 (5)
C12	0.0211 (7)	0.0221 (8)	0.0202 (7)	0.0079 (6)	0.0013 (6)	0.0015 (6)
C16	0.0246 (8)	0.0237 (8)	0.0180 (7)	0.0081 (6)	0.0006 (6)	0.0017 (6)
C8	0.0202 (7)	0.0169 (7)	0.0199 (7)	0.0050 (6)	0.0021 (6)	0.0029 (5)
C9	0.0223 (7)	0.0254 (8)	0.0192 (7)	0.0099 (6)	0.0033 (6)	0.0006 (6)
C20	0.0208 (7)	0.0211 (7)	0.0210 (7)	0.0077 (6)	0.0007 (6)	0.0031 (6)
C10	0.0195 (7)	0.0242 (8)	0.0229 (8)	0.0091 (6)	0.0011 (6)	0.0019 (6)
C1	0.0276 (8)	0.0288 (8)	0.0190 (7)	0.0107 (7)	−0.0046 (6)	0.0008 (6)
C19	0.0272 (8)	0.0302 (8)	0.0258 (8)	0.0147 (7)	0.0010 (6)	−0.0017 (6)
C15	0.0299 (8)	0.0294 (8)	0.0284 (8)	0.0164 (7)	0.0004 (6)	0.0021 (6)

O4—C3	1.2107 (18)	C11—C20	1.397 (2)
O2—C3	1.3436 (17)	C5—C10	1.392 (2)
O2—C1	1.4427 (17)	C12—H12	0.9500
O18—C17	1.3694 (17)	C16—H16	0.9500
O18—C19	1.4308 (18)	C8—C9	1.399 (2)
O14—C13	1.3676 (18)	C9—H9	0.9500
O14—C15	1.4278 (18)	C9—C10	1.386 (2)
C3—C5	1.485 (2)	C20—H20	0.9500
C6—H6	0.9500	C10—H10	0.9500
C6—C7	1.391 (2)	C1—H1A	0.9800
C6—C5	1.391 (2)	C1—H1B	0.9800
C17—C16	1.389 (2)	C1—H1C	0.9800
C17—C20	1.393 (2)	C19—H19A	0.9800
C13—C12	1.399 (2)	C19—H19B	0.9800
C13—C16	1.389 (2)	C19—H19C	0.9800
C7—H7	0.9500	C15—H15A	0.9800
C7—C8	1.396 (2)	C15—H15B	0.9800
C11—C12	1.400 (2)	C15—H15C	0.9800
C11—C8	1.487 (2)

C3—O2—C1	115.97 (11)	C7—C8—C11	121.35 (13)
C17—O18—C19	117.27 (11)	C7—C8—C9	117.57 (13)
C13—O14—C15	117.93 (12)	C9—C8—C11	121.09 (13)
O4—C3—O2	123.42 (13)	C8—C9—H9	119.4
O4—C3—C5	125.19 (13)	C10—C9—C8	121.19 (13)
O2—C3—C5	111.38 (12)	C10—C9—H9	119.4
C7—C6—H6	120.0	C17—C20—C11	120.10 (13)
C5—C6—H6	120.0	C17—C20—H20	119.9
C5—C6—C7	119.98 (13)	C11—C20—H20	119.9
O18—C17—C16	115.76 (13)	C5—C10—H10	119.7
O18—C17—C20	123.83 (13)	C9—C10—C5	120.53 (14)
C16—C17—C20	120.40 (13)	C9—C10—H10	119.7
O14—C13—C12	124.10 (13)	O2—C1—H1A	109.5
O14—C13—C16	114.75 (13)	O2—C1—H1B	109.5
C16—C13—C12	121.14 (13)	O2—C1—H1C	109.5
C6—C7—H7	119.2	H1A—C1—H1B	109.5
C6—C7—C8	121.62 (13)	H1A—C1—H1C	109.5
C8—C7—H7	119.2	H1B—C1—H1C	109.5
C12—C11—C8	120.57 (13)	O18—C19—H19A	109.5
C20—C11—C12	119.93 (14)	O18—C19—H19B	109.5
C20—C11—C8	119.50 (13)	O18—C19—H19C	109.5
C6—C5—C3	119.12 (13)	H19A—C19—H19B	109.5
C6—C5—C10	119.11 (14)	H19A—C19—H19C	109.5
C10—C5—C3	121.77 (13)	H19B—C19—H19C	109.5
C13—C12—C11	119.01 (13)	O14—C15—H15A	109.5
C13—C12—H12	120.5	O14—C15—H15B	109.5
C11—C12—H12	120.5	O14—C15—H15C	109.5
C17—C16—C13	119.41 (14)	H15A—C15—H15B	109.5
C17—C16—H16	120.3	H15A—C15—H15C	109.5
C13—C16—H16	120.3	H15B—C15—H15C	109.5

O4—C3—C5—C6	−1.2 (2)	C12—C11—C8—C7	28.9 (2)
O4—C3—C5—C10	177.90 (14)	C12—C11—C8—C9	−150.86 (14)
O2—C3—C5—C6	179.48 (13)	C12—C11—C20—C17	0.9 (2)
O2—C3—C5—C10	−1.4 (2)	C16—C17—C20—C11	−1.4 (2)
O18—C17—C16—C13	179.66 (13)	C16—C13—C12—C11	−0.4 (2)
O18—C17—C20—C11	−179.97 (13)	C8—C11—C12—C13	179.45 (13)
O14—C13—C12—C11	−179.23 (13)	C8—C11—C20—C17	−178.56 (13)
O14—C13—C16—C17	178.85 (13)	C8—C9—C10—C5	−0.3 (2)
C3—C5—C10—C9	−178.42 (14)	C20—C17—C16—C13	1.0 (2)
C6—C7—C8—C11	179.75 (13)	C20—C11—C12—C13	0.0 (2)
C6—C7—C8—C9	−0.4 (2)	C20—C11—C8—C7	−151.58 (14)
C6—C5—C10—C9	0.7 (2)	C20—C11—C8—C9	28.6 (2)
C7—C6—C5—C3	178.20 (13)	C1—O2—C3—O4	−0.2 (2)
C7—C6—C5—C10	−0.9 (2)	C1—O2—C3—C5	179.10 (12)
C7—C8—C9—C10	0.2 (2)	C19—O18—C17—C16	167.89 (13)
C11—C8—C9—C10	179.99 (13)	C19—O18—C17—C20	−13.5 (2)
C5—C6—C7—C8	0.8 (2)	C15—O14—C13—C12	−9.0 (2)
C12—C13—C16—C17	−0.1 (2)	C15—O14—C13—C16	172.12 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.89	3.7702 (19)	154
C7—H7···O4ⁱⁱ	0.95	2.85	3.4607 (19)	123
C12—H12···O4ⁱⁱ	0.95	2.71	3.644 (2)	170
C16—H16···O14ⁱⁱⁱ	0.95	2.65	3.514 (2)	151
C1—H1A···O4^iv	0.98	2.73	3.665 (2)	159
C19—H19A···O18^v	0.98	2.65	3.538 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.89	3.7702 (19)	154
C7—H7⋯O4ⁱⁱ	0.95	2.85	3.4607 (19)	123
C12—H12⋯O4ⁱⁱ	0.95	2.71	3.644 (2)	170
C16—H16⋯O14ⁱⁱⁱ	0.95	2.65	3.514 (2)	151
C1—H1A⋯O4^iv	0.98	2.73	3.665 (2)	159
C19—H19A⋯O18^v	0.98	2.65	3.538 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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. 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

5. 2-(Biphenyl-4-yl)acetic acid (felbinac).

Authors: Bernard Van Eerdenbrugh; Phillip E Fanwick; Lynne S Taylor
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-09-25

6. 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

7. Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane.

Authors: Brad M Rosen; Chenghong Huang; Virgil Percec
Journal: Org Lett Date: 2008-05-17 Impact factor: 6.005

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

Authors: Manu Lahtinen; Kalle Nättinen; Sami Nummelin
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-02-16