3,4-Dimeth­oxy-4′-methyl­biphen­yl

Lahtinen, M.; Nummelin, S.

doi:10.1107/S1600536813008957

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o681

https://doi.org/10.1107/S1600536813008957

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3,4-Dimethoxy-4′-methylbiphenyl

Manu Lahtinen ^a and Sami Nummelin ^b ^*

^aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 JY, Finland, and ^bMolecular 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 2 April 2013; accepted 2 April 2013; online 10 April 2013)

In the title compound, C₁₅H₁₆O₂, the dihedral angle between the planes of the aromatic rings is 30.5 (2)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a two-dimensional network lying parallel to (100).

Related literature

For structural studies of related biphenyl derivatives, see Lahtinen et al. (2013a ,b ,c ); Li et al. (2012a ,b ). For details of the synthesis, see: Percec et al. (2004 , 2006 ); Wolfe et al. (1999 ). For details of various cross-coupling reactions, see: Corbet & Mignani (2006 ); Miyaura et al. (1981 ); Miyaura & Suzuki (1995 ); Percec et al. (2004); Wolfe et al. (1999). For self-assembling supramolecular dendrons based on 3,4-branched biphenyls, see: Percec et al. (2006, 2007 ). For hollow supramolecular dendrimers, see Peterca et al. (2006 ); Percec et al. (2008 ). For dendritic polyaryl esters, see Nummelin et al. (2000 ).

Experimental

Crystal data

C₁₅H₁₆O₂
M_r = 228.28
Monoclinic, P 2₁ /c
a = 17.7430 (9) Å
b = 8.7581 (3) Å
c = 8.1135 (3) Å
β = 101.795 (5)°
V = 1234.17 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 123 K
0.36 × 0.26 × 0.04 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ) T_min = 0.880, T_max = 0.977
4273 measured reflections
2282 independent reflections
1844 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.143
S = 1.07
2282 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O16ⁱ	0.98	2.57	3.389 (2)	141
C15—H15C⋯O16ⁱⁱ	0.98	2.42	3.356 (2)	160
C4—H4⋯Cg2ⁱⁱ	0.95	2.96	3.7807 (18)	145
C17—H17B⋯Cg2ⁱⁱⁱ	0.98	2.83	3.7119 (19)	150
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813008957/fj2625sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008957/fj2625Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008957/fj2625Isup3.cml

checkCIF report

Comment top

Percec-type biphenyl dendrons (Percec et al. 2006, 2007) are synthesized in a multi-step reaction sequence wherein the key synthetic step is the formation of sp²–sp² carbon–carbon bonds. This is achieved using various cross-coupling reactions (Corbet & Mignani 2006). The title compound is synthesized in a gram-scale using the Suzuki-Miyaura cross-coupling reaction (Miyaura & Suzuki 1995), catalyzed by either palladium (Miyaura et al. 1981; Wolfe et al. 1999) or nickel (Percec et al. 2004, 2006). Biphenyl derivatives expand the scope and limitations of aryl ethers and esters (Nummelin et al. 2000) that serve as tectons for the construction of amphiphilic dendrons. Percec-type dendrons self-assemble into hollow and non-hollow cylindrical and spherical supramolecular dendrimers that further self-organize into hexagonal and cubic lattices (Percec et al. 2006, 2007, 2008; Peterca et al. 2006). As a contribution to a structural study of biphenyl derivatives (Lahtinen et al. 2013a,b,c; Li et al. 2012a,b) we report here the title compound 3,4-dimethoxy-4'-methyl biphenyl (I).

The compound (I) crystallizes in monoclinic P2₁/c (No. 14) spacegroup having a single molecule in an asymmetric unit (Figure 1). The intramolecular dihedral angle between the phenyl rings is 30.5 (2)° [C(4)–C(5)–C(8)–C(9)] thereby being analogous to those found in similar biphenyls reported earlier (Lahtinen et al. 2013a,b,c). The methoxy groups at 3- and 4-positions are co-planar in relation to the phenyl ring [C8>C13] with dihedral angles of -5.0 (2)° and 1.4 (2)°, respectively. Molecules are packed in head-to-head (methoxy-phenyl part) and tail-to-tail (methyl-phenyl part) formation (Figure 2) in zigzagged rows running parallel to (201) plane. By this, a columnar packing is formed in which methoxy and methyl layers alternate along a-axis (Figures 3 and 4). Network of C–H···π interactions occur between methoxy H atoms and phenyl groups with distance of 4.218 (2) Å. Infinite network of edge-to-face π–π interactions occur between phenyl rings (Figure 5) troughout the lattice along with (011) plane with distance of 5.047 (1) Å. Also weak C–H···O hydrogen bond network exist between the adjacent methoxy groups with D···A distances varying from 3.356 (2) to 3.694 (2) Å.

Related literature top

For structural studies of related biphenyl derivatives, see Lahtinen et al. (2013a,b,c); Li et al. (2012a,b). For details of the synthesis, see: Percec et al. (2004, 2006); Wolfe et al. (1999). For details of various cross-coupling reactions, see: Corbet & Mignani (2006); Miyaura et al. (1981); Miyaura & Suzuki (1995); Percec et al. (2004); Wolfe et al. (1999). For self-assembling supramolecular dendrons based on 3,4-branched biphenyls, see: Percec et al. (2006, 2007). For hollow supramolecular dendrimers, see Peterca et al. (2006); Percec et al. (2008). For dendritic polyaryl esters, see Nummelin et al. (2000).

Experimental top

A dry Schlenk-tube was charged with 4-methylphenylboronic acid (6.0 g, 44.1 mmol), potassium fluoride (5.1 g, 88.3 mmol), 1-bromo-3,4-dimethoxybenzene (6.4 g, 29.4 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. 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 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 Na₂SO₄. The crude product was purified by flash column chromatography: silica gel/CH₂Cl₂. Yield: 6.2 g (92%) of a white crystalline solid. Crystals suitable for a single-crystal structure determination were obtained from a slow evaporation of ethanol.

Structure description top

For structural studies of related biphenyl derivatives, see Lahtinen et al. (2013a,b,c); Li et al. (2012a,b). For details of the synthesis, see: Percec et al. (2004, 2006); Wolfe et al. (1999). For details of various cross-coupling reactions, see: Corbet & Mignani (2006); Miyaura et al. (1981); Miyaura & Suzuki (1995); Percec et al. (2004); Wolfe et al. (1999). For self-assembling supramolecular dendrons based on 3,4-branched biphenyls, see: Percec et al. (2006, 2007). For hollow supramolecular dendrimers, see Peterca et al. (2006); Percec et al. (2008). For dendritic polyaryl esters, see Nummelin et al. (2000).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure and atomic labeling of the title compound showing 50% probability displacement ellipsoids.
	Fig. 2. In zigzag formation packed molecule rows along (201)-plane. Hydrogen atoms are omitted for clarity.
	Fig. 3. Packing of molecules along b-axis. Hydrogen atoms are omitted for clarity.
	Fig. 4. Packing of molecules along c axis. Hydrogen atoms are omitted for clarity.
	Fig. 5. Weak hydrogen bond C–H···O (blue dashed lines), C–H···π and edge-to-face π–π contacts shown between the molecules.

3,4-Dimethoxy-4'-methylbiphenyl top

Crystal data top

C₁₅H₁₆O₂	F(000) = 488
M_r = 228.28	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
a = 17.7430 (9) Å	Cell parameters from 1622 reflections
b = 8.7581 (3) Å	θ = 5.1–76.7°
c = 8.1135 (3) Å	µ = 0.64 mm⁻¹
β = 101.795 (5)°	T = 123 K
V = 1234.17 (9) Å³	Plate, colourless
Z = 4	0.36 × 0.26 × 0.04 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2282 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1844 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.3953 pixels mm^-1	θ_max = 69.0°, θ_min = 5.1°
ω scans	h = −18→21
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −10→7
T_min = 0.880, T_max = 0.977	l = −9→9
4273 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0735P)² + 0.0799P] where P = (F_o² + 2F_c²)/3
2282 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³
0 constraints

Crystal data top

C₁₅H₁₆O₂	V = 1234.17 (9) Å³
M_r = 228.28	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 17.7430 (9) Å	µ = 0.64 mm⁻¹
b = 8.7581 (3) Å	T = 123 K
c = 8.1135 (3) Å	0.36 × 0.26 × 0.04 mm
β = 101.795 (5)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2282 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	1844 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.977	R_int = 0.038
4273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.07	Δρ_max = 0.23 e Å⁻³
2282 reflections	Δρ_min = −0.31 e Å⁻³
157 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
O16	0.89457 (7)	0.46978 (13)	0.00350 (15)	0.0335 (3)
O14	0.94276 (7)	0.60539 (14)	0.28726 (15)	0.0353 (3)
C9	0.82177 (9)	0.56204 (18)	0.37788 (19)	0.0282 (3)
H9	0.8400	0.6111	0.4829	0.034*
C11	0.84258 (10)	0.47747 (17)	0.10680 (19)	0.0283 (4)
C10	0.86951 (10)	0.55131 (17)	0.2626 (2)	0.0284 (3)
C8	0.74672 (9)	0.50130 (17)	0.34160 (19)	0.0278 (3)
C12	0.76904 (10)	0.41966 (19)	0.0695 (2)	0.0317 (4)
H12	0.7506	0.3713	−0.0358	0.038*
C13	0.72128 (10)	0.43187 (19)	0.1867 (2)	0.0310 (4)
H13	0.6705	0.3918	0.1594	0.037*
C4	0.70104 (10)	0.63163 (19)	0.58078 (19)	0.0312 (4)
H4	0.7379	0.7101	0.5799	0.037*
C3	0.65286 (10)	0.6385 (2)	0.6963 (2)	0.0344 (4)
H3	0.6577	0.7212	0.7734	0.041*
C6	0.64005 (10)	0.39913 (18)	0.4706 (2)	0.0317 (4)
H6	0.6349	0.3161	0.3937	0.038*
C7	0.59199 (10)	0.40748 (19)	0.5854 (2)	0.0340 (4)
H7	0.5543	0.3303	0.5851	0.041*
C5	0.69597 (9)	0.51097 (18)	0.46610 (19)	0.0281 (4)
C2	0.59771 (10)	0.5262 (2)	0.7009 (2)	0.0331 (4)
C1	0.54666 (11)	0.5331 (2)	0.8280 (2)	0.0418 (4)
H1A	0.5696	0.6014	0.9203	0.063*
H1B	0.5413	0.4305	0.8726	0.063*
H1C	0.4958	0.5717	0.7737	0.063*
C17	0.86955 (12)	0.3987 (2)	−0.1569 (2)	0.0401 (4)
H17A	0.8250	0.4540	−0.2208	0.060*
H17B	0.8551	0.2926	−0.1409	0.060*
H17C	0.9114	0.4009	−0.2191	0.060*
C15	0.97056 (11)	0.6901 (2)	0.4385 (2)	0.0429 (5)
H15A	1.0228	0.7267	0.4391	0.064*
H15B	0.9713	0.6241	0.5363	0.064*
H15C	0.9366	0.7775	0.4435	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O16	0.0440 (7)	0.0297 (6)	0.0324 (6)	−0.0001 (5)	0.0209 (5)	−0.0024 (4)
O14	0.0392 (7)	0.0340 (6)	0.0368 (6)	−0.0065 (5)	0.0173 (5)	−0.0074 (5)
C9	0.0380 (8)	0.0238 (7)	0.0255 (7)	0.0008 (6)	0.0128 (6)	0.0006 (5)
C11	0.0389 (8)	0.0230 (7)	0.0268 (7)	0.0044 (6)	0.0159 (6)	0.0036 (5)
C10	0.0362 (8)	0.0208 (7)	0.0307 (8)	0.0001 (6)	0.0129 (6)	0.0023 (6)
C8	0.0351 (8)	0.0235 (7)	0.0273 (7)	0.0017 (6)	0.0122 (6)	0.0024 (6)
C12	0.0406 (9)	0.0304 (8)	0.0256 (7)	0.0018 (6)	0.0101 (6)	−0.0017 (6)
C13	0.0351 (8)	0.0311 (8)	0.0285 (8)	−0.0003 (6)	0.0108 (6)	−0.0009 (6)
C4	0.0396 (9)	0.0286 (8)	0.0278 (7)	−0.0017 (6)	0.0124 (6)	−0.0003 (6)
C3	0.0448 (10)	0.0336 (9)	0.0278 (8)	0.0034 (7)	0.0146 (7)	−0.0020 (6)
C6	0.0391 (9)	0.0266 (8)	0.0318 (8)	0.0004 (6)	0.0131 (6)	−0.0003 (6)
C7	0.0360 (9)	0.0315 (8)	0.0382 (9)	0.0005 (6)	0.0166 (7)	0.0048 (6)
C5	0.0344 (8)	0.0263 (8)	0.0252 (7)	0.0030 (6)	0.0101 (6)	0.0036 (6)
C2	0.0365 (8)	0.0370 (9)	0.0285 (8)	0.0065 (7)	0.0130 (6)	0.0059 (6)
C1	0.0417 (10)	0.0537 (11)	0.0347 (9)	0.0078 (8)	0.0186 (7)	0.0044 (8)
C17	0.0522 (11)	0.0454 (10)	0.0264 (8)	0.0081 (8)	0.0165 (7)	−0.0011 (7)
C15	0.0435 (10)	0.0394 (9)	0.0497 (10)	−0.0106 (7)	0.0188 (8)	−0.0172 (8)

Geometric parameters (Å, º) top

O16—C11	1.3689 (19)	C3—H3	0.9500
O16—C17	1.429 (2)	C3—C2	1.393 (3)
O14—C10	1.359 (2)	C6—H6	0.9500
O14—C15	1.432 (2)	C6—C7	1.388 (2)
C9—H9	0.9500	C6—C5	1.400 (2)
C9—C10	1.388 (2)	C7—H7	0.9500
C9—C8	1.408 (2)	C7—C2	1.389 (3)
C11—C10	1.413 (2)	C2—C1	1.507 (2)
C11—C12	1.375 (3)	C1—H1A	0.9800
C8—C13	1.386 (2)	C1—H1B	0.9800
C8—C5	1.487 (2)	C1—H1C	0.9800
C12—H12	0.9500	C17—H17A	0.9800
C12—C13	1.401 (2)	C17—H17B	0.9800
C13—H13	0.9500	C17—H17C	0.9800
C4—H4	0.9500	C15—H15A	0.9800
C4—C3	1.393 (2)	C15—H15B	0.9800
C4—C5	1.399 (2)	C15—H15C	0.9800

C11—O16—C17	117.15 (14)	C5—C6—H6	119.5
C10—O14—C15	117.27 (13)	C6—C7—H7	119.3
C10—C9—H9	119.5	C6—C7—C2	121.46 (16)
C10—C9—C8	121.00 (15)	C2—C7—H7	119.3
C8—C9—H9	119.5	C4—C5—C8	121.97 (15)
O16—C11—C10	115.04 (14)	C4—C5—C6	117.45 (15)
O16—C11—C12	125.13 (15)	C6—C5—C8	120.57 (14)
C12—C11—C10	119.83 (14)	C3—C2—C1	120.94 (16)
O14—C10—C9	125.05 (15)	C7—C2—C3	117.72 (15)
O14—C10—C11	115.43 (14)	C7—C2—C1	121.33 (17)
C9—C10—C11	119.51 (15)	C2—C1—H1A	109.5
C9—C8—C5	120.98 (14)	C2—C1—H1B	109.5
C13—C8—C9	118.30 (14)	C2—C1—H1C	109.5
C13—C8—C5	120.72 (15)	H1A—C1—H1B	109.5
C11—C12—H12	120.0	H1A—C1—H1C	109.5
C11—C12—C13	120.10 (15)	H1B—C1—H1C	109.5
C13—C12—H12	120.0	O16—C17—H17A	109.5
C8—C13—C12	121.24 (15)	O16—C17—H17B	109.5
C8—C13—H13	119.4	O16—C17—H17C	109.5
C12—C13—H13	119.4	H17A—C17—H17B	109.5
C3—C4—H4	119.5	H17A—C17—H17C	109.5
C3—C4—C5	121.00 (16)	H17B—C17—H17C	109.5
C5—C4—H4	119.5	O14—C15—H15A	109.5
C4—C3—H3	119.4	O14—C15—H15B	109.5
C4—C3—C2	121.26 (15)	O14—C15—H15C	109.5
C2—C3—H3	119.4	H15A—C15—H15B	109.5
C7—C6—H6	119.5	H15A—C15—H15C	109.5
C7—C6—C5	121.10 (15)	H15B—C15—H15C	109.5

O16—C11—C10—O14	0.6 (2)	C4—C3—C2—C7	−0.4 (3)
O16—C11—C10—C9	−178.57 (13)	C4—C3—C2—C1	179.02 (16)
O16—C11—C12—C13	178.85 (14)	C3—C4—C5—C8	179.95 (14)
C9—C8—C13—C12	1.1 (2)	C3—C4—C5—C6	0.9 (2)
C9—C8—C5—C4	30.5 (2)	C6—C7—C2—C3	0.8 (3)
C9—C8—C5—C6	−150.44 (16)	C6—C7—C2—C1	−178.60 (16)
C11—C12—C13—C8	−0.2 (2)	C7—C6—C5—C8	−179.55 (15)
C10—C9—C8—C13	−0.7 (2)	C7—C6—C5—C4	−0.5 (2)
C10—C9—C8—C5	179.17 (14)	C5—C8—C13—C12	−178.85 (15)
C10—C11—C12—C13	−0.9 (2)	C5—C4—C3—C2	−0.4 (3)
C8—C9—C10—O14	−179.46 (15)	C5—C6—C7—C2	−0.4 (3)
C8—C9—C10—C11	−0.4 (2)	C17—O16—C11—C10	−178.82 (14)
C12—C11—C10—O14	−179.61 (14)	C17—O16—C11—C12	1.4 (2)
C12—C11—C10—C9	1.2 (2)	C15—O14—C10—C9	−5.0 (2)
C13—C8—C5—C4	−149.58 (16)	C15—O14—C10—C11	175.86 (15)
C13—C8—C5—C6	29.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O16ⁱ	0.98	2.57	3.389 (2)	141
C15—H15C···O16ⁱⁱ	0.98	2.42	3.356 (2)	160
C4—H4···Cg2ⁱⁱ	0.95	2.96	3.7807 (18)	145
C17—H17B···Cg2ⁱⁱⁱ	0.98	2.83	3.7119 (19)	150

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆O₂
M_r	228.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	17.7430 (9), 8.7581 (3), 8.1135 (3)
β (°)	101.795 (5)
V (Å³)	1234.17 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.36 × 0.26 × 0.04

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas)
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.880, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	4273, 2282, 1844
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.143, 1.07
No. of reflections	2282
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.31

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).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O16ⁱ	0.98	2.57	3.389 (2)	141
C15—H15C···O16ⁱⁱ	0.98	2.42	3.356 (2)	160
C4—H4···Cg2ⁱⁱ	0.95	2.96	3.7807 (18)	145
C17—H17B···Cg2ⁱⁱⁱ	0.98	2.83	3.7119 (19)	150

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

Acknowledgements

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

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