organic compounds
3,5-Dimethoxy-4′-methylbiphenyl
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
The title compound, C15H16O2, crystallizes with three independent molecules in the 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
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Data collection: CrysAlis PRO (Agilent, 2010); cell 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
10.1107/S1600536813006053/fj2619sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813006053/fj2619Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813006053/fj2619Isup3.cml
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
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 were obtained from a slow evaporation of ethanol.Hydrogen atoms were calculated to their positions as riding atoms (C host) using isotropic displacement parameters that were fixed to be 1.2 or 1.5 times larger than those of the attached non-hydrogen atom.
Data collection: CrysAlis PRO (Agilent, 2010); cell
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).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. |
C15H16O2 | Dx = 1.239 Mg m−3 |
Mr = 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 |
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 | Rint = 0.028 |
Detector resolution: 5.1977 pixels mm-1 | θmax = 68.0°, θmin = 3.9° |
ω scans | h = −8→8 |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) | k = −12→18 |
Tmin = 0.900, Tmax = 0.979 | l = −35→40 |
8494 measured reflections |
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(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max = 0.004 |
S = 1.04 | Δρmax = 0.21 e Å−3 |
5862 reflections | Δρmin = −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) |
C15H16O2 | V = 3671.88 (16) Å3 |
Mr = 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 |
Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer | 5862 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) | 5181 reflections with I > 2σ(I) |
Tmin = 0.900, Tmax = 0.979 | Rint = 0.028 |
8494 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.094 | Δρmax = 0.21 e Å−3 |
S = 1.04 | Δρmin = −0.22 e Å−3 |
5862 reflections | Absolute structure: Flack (1983), 2062 Friedel pairs |
470 parameters | Absolute structure parameter: 0.09 (19) |
0 restraints |
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 | Uiso*/Ueq | ||
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* |
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) |
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) |
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···O34iv | 0.98 | 2.68 | 3.521 (3) | 143 |
C52—H52A···O17v | 0.98 | 2.63 | 3.398 (3) | 136 |
C18—H18A···Cg1iii | 0.98 | 2.89 | 3.686 (3) | 142 |
C16—H16C···Cg2iv | 0.98 | 2.62 | 3.366 (3) | 139 |
C33—H33B···Cg3iii | 0.98 | 3.05 | 3.476 (3) | 115 |
C52—H52B···Cg4v | 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···Cg6vi | 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 |
Mr | 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) |
Tmin, Tmax | 0.900, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8494, 5862, 5181 |
Rint | 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 |
Δρmax, Δρmin (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).
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···O34iv | 0.98 | 2.68 | 3.521 (3) | 143 |
C52—H52A···O17v | 0.98 | 2.63 | 3.398 (3) | 136 |
C18—H18A···Cg1iii | 0.98 | 2.89 | 3.686 (3) | 142 |
C16—H16C···Cg2iv | 0.98 | 2.62 | 3.366 (3) | 139 |
C33—H33B···Cg3iii | 0.98 | 3.05 | 3.476 (3) | 115 |
C52—H52B···Cg4v | 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···Cg6vi | 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).
References
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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.
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.