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

The title compound, C15H16O2, crystallizes with three independent mol-ecules in the asymmetric unit. The intra-molecular torsion angle between the aromatic rings of each mol-ecule are -36.4 (3), 41.3 (3) and -37.8 (3)°. In the crystal, the complicated packing of the mol-ecules forms wave-like layers along the b and c axes. The mol-ecules are connected via extensive meth-oxy-phenyl C-H⋯π inter-actions. A weak C-H⋯O hydrogen-bonding network also exists between meth-oxy O atoms and aromatic or meth-oxy 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

C15H16O2

M = 228.28

Orthorhombic,

a = 7.16505 (18) Å

b = 15.3511 (4) Å

c = 33.3834 (8) Å

V = 3671.88 (16) Å3

Z = 12

Cu Kα radiation

μ = 0.64 mm−1

T = 123 K

0.31 × 0.07 × 0.04 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.900, T max = 0.979

8494 measured reflections

5862 independent reflections

5181 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.094

S = 1.04

5862 reflections

470 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 2062 Friedel pairs

Flack parameter: 0.09 (19)

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006053/fj2619sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006053/fj2619Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006053/fj2619Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	Flack parameter: 0.09 (19)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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