Two terphenyl-based diol hosts and corresponding solvent inclusions with di­methyl­formamide and aceto­nitrile

Having reference to an elongated structural modification of 2,2′-bis­­(hydroxy­diphenylmethyl)biphenyl, (I), the two 1,1′:4′,1′′-terphenyl-based diol hosts 2,2′′-bis­(hydroxydiphenylmethyl)-1,1′:4′,1′′-terphenyl, C₄₄H₃₄O₂, (II), and 2,2′′-bis­[hydroxy­bis­(4-methyl­phenyl)methyl]-1,1′:4′,1′′-terphenyl, C₄₈H₄₂O₂, (III), have been synthesized and studied with regard to their crystal structures involving different inclusions, i.e. (II) with di­methyl­formamide (DMF), C₄₄H₃₄O₂·C₂H₆NO, denoted (IIa), (III) with DMF, C₄₈H₄₂O₂·C₂H₆NO, denoted (IIIa), and (III) with aceto­nitrile, C₄₈H₄₂O₂·CH₃CN, denoted (IIIb). In the solvent-free crystals of (II) and (III), the hy­droxy H atoms are involved in intra­molecular O—H...π hydrogen bonding, with the central arene ring of the terphenyl unit acting as an acceptor. The corresponding crystal structures are stabilized by inter­molecular C—H...π contacts. Due to the distinctive acceptor character of the included DMF solvent species in the crystal structures of (IIa) and (IIIa), the guest mol­ecule is coordinated to the host via O—H...O=C hydrogen bonding. In both crystal structures, infinite strands composed of alternating host and guest mol­ecules represent the basic supra­molecular aggregates. Within a given strand, the O atom of the solvent mol­ecule acts as a bifurcated acceptor. Similar to the solvent-free cases, the hy­droxy H atoms in inclusion structure (IIIb) are involved in intra­molecular hydrogen bonding, and there is thus a lack of host–guest inter­action. As a result, the solvent mol­ecules are accommodated as C—H...N hydrogen-bonded inversion-symmetric dimers in the channel-like voids of the host lattice.

S1. Introduction

Compounds creating open structures in the crystalline state may inter­act with secondary molecules to form host–guest inclusion species (Atwood et al., 1991). Different strategies for the design of corresponding host compounds have been developed (Bishop, 1996; Desiraju, 1996), with the diol host (Toda, 1991) and coordination clathrate (Weber & Czugler, 1988) concepts being two of the best known. Bringing both these concepts together has given rise to a number of versatile hosts capable of forming a great number of crystalline inclusion compounds (Weber, 1996). Nevertheless, based on specific inter­action modes, they show distinct guest selectivity, e.g. regarding the inclusion of organic solvents (Nangia, 2004; Caira & Nassimbeni, 1996). A prototype host compound of this kind is denoted (I) in Scheme 1 (Toda et al., 1989; Csöregh et al., 2004). Elongation of the central bi­phenyl axis in (I) by exchange for a 1,1':4',1''-terphenyl group, as in (II), and in addition substitution of the lateral phenyl groups of (II) by tolyl groups resulting in compound (III), should also lead to modified host–guest inter­action and inclusion behaviour (Klien et al., 2013). We report here, for the first time, the synthesis and crystal structures of the new host compounds 2,2''-bis­(hy­droxy­diphenyl­methyl)-1,1':4',1''-terphenyl, (II), and 2,2''-bis­[hy­droxy­bis­(4-methyl­phenyl)­methyl]-1,1':4',1''-terphenyl, (III), in their solvent-free state, and of the corresponding solvent-inclusion compounds of (II) and (III) with DMF, i.e. (IIa) and (IIIa), respectively, and of (III) with aceto­nitrile, (IIIb).

S2. Experimental

S2.1. Physical measurements

Melting points (uncorrected) were measured on a PHMK Rapido (Dresden Analytic) microscope heating stage. IR spectra were recorded with a Nicolet FT–IR 510 spectrometer. ¹H and ¹³C NMR spectra (p.p.m., inter­nal standard TMS) were obtained using a Bruker Avance III 500 spectrometer, and ESI–MS data were recorded with a [Manufacturer?] 1050/5989B instrument.

S2.2. Synthesis and crystallization

Organic solvents were purified by standard procedures. The starting compounds (benzo­phenone and 4,4'-di­methyl­benzo­phenone) were purchased from commercial sources. 2,2''-Di­iodo-1,1':4',1''-terphenyl was prepared following the literature procedures of Horhant et al. (2006) and Poriel et al. (2007).

Compound (II) was prepared by the addition of a solution of n-butyl­lithium (1.6 M in hexane, 1.5 ml, 2.3 mmol) to a cold solution (195 K) of 2,2''-di­iodo-1,1':4',1''-terphenyl (0.5 g, 1.0 mmol) in dry tetra­hydro­furan (THF; 20 ml). After stirring for 45 min, a solution of benzo­phenone (0.36 g, 2.1 mmol) in benzene (4 ml) was added. The colourless reaction mixture was warmed to room temperature and stirred for 4 h. The solution was extracted twice with di­ethyl ether. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained yellow oil was suspended in n-hexane and heated under reflux to dissolve the residual educts and side products. After cooling the suspension to room temperature, the desired compound was obtained as a white solid. Colourless crystals of (II) were isolated by recrystallization from ethanol (yield 27.1%; m.p. 510–511 K). ESI–MS [M - H]^- (m/z): 593.2; IR (KBr, ν, cm^-1): 3557, 3085, 3056, 3022, 1961, 1597, 1489, 1473, 1448, 1337, 1280, 1185, 1160, 1033, 1021, 1005, 907, 891, 840, 758, 701, 599; ¹H NMR (500.1 MHz, CDCl₃, δ, p.p.m.): 2.86 (2H, s, OH), 6.60 (4H, s, ArH), 6.77 (2H, d, ³J_HH = 7.40 Hz, ArH), 7.08 (2H, d, ³J_HH = 7.43 Hz, ArH), 7.17–7.20 (10H, m, ArH), 7.25-7.30 (14H, m, ArH); ¹³C NMR (125.7 MHz, CDCl₃, δ, p.p.m.): 85.35, 126.90, 127.17, 127.84, 128.03, 128.97, 130.00, 132.41, 140.63, 141.09, 145.28, 147.40. Analysis, calculated for C₄₄H₃₄O₂: C 88.9, H 5.8%; found: C 88.4, H 6.0%.

Following an analogous procedure, compound (III) was prepared using 4,4'-di­methyl­benzo­phenone (4.4 g, 2.1 mmol). Crystals of (III) suitable for X-ray diffraction were obtained from an ethanol solution (yield 16.2%; m.p. 525–526 K). ESI–MS (m/z): 649.3 [M - H]^-; IR (KBr, ν, cm^-1): 3554, 3056, 3025, 2920, 2866, 1917, 1609, 1508, 1470, 1407, 1335, 1280, 1185, 1157, 1033, 1021, 1005, 922, 903, 846, 815, 758; ¹H NMR (500.1 MHz, CDCl₃, δ, p.p.m.): 2.34 (12H, s, methyl), 2.77 (2H, s, OH), 6.62 (4H, s, ArH), 6.80 (2H, d, ³J = 7.90 Hz, ArH), 7.03 (8H, d, ³J_HH = 8.50 Hz, ArH), 7.02–7.09 (10H, m, Ar—H), 7.17 (2H, t, ³J_HH = 8.00 Hz, ArH), 7.27 (2H, t, ³J_HH = 7.25 Hz, ArH); ¹³C NMR (125.7 MHz, CDCl₃, δ, p.p.m.): 21.05, 83.11, 126.37, 126.71, 127.89, 128.45, 128.90, 130.02, 132.34, 136.59, 140.59, 141.19, 144.80, 145.48. Analysis, calculated for C₄₈H₄₂O₂: C 88.6, H 6.5%; found: C 87.9, H 6.9%.

How were the solvent-inclusion compounds prepared?

S2.3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. In compounds (II), (IIa), (III), (IIIa) and (IIIb), all H atoms were placed geometrically in idealized positions and allowed to ride on their parent atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic H, and with C—H = 0.98 Å and O—H = 0.84 Å, and U_iso(H) = 1.5U_eq(C) for methyl and hy­droxy groups, respectively.

S3. Results and discussion

Perspective views of the molecular structures of (II) and (III), and of the solvent-inclusion compounds (IIa), (IIIa) and (IIIb), including the atom labelling and ring specifications, are shown in Fig. 1. The packing diagrams are presented in Figs. 2 and 3, respectively. Information regarding hydrogen-bond inter­actions in the crystal structures is presented in Tables 2–6.

In the molecular structures, the 1,1':4',1''-terphenyl groups are significantly twisted. The twist angles between the planes of the arene rings of this unit range from 52.8 (1)/57.7 (1)° in (IIIa) to 72.2 (1)/89.3 (1)° in (II). The bond lengths within the terphenyl group agree well with those found in the crystal structures of 2,2''-disubstituted derivatives of p-terphenyl (Lunazzi et al., 2005; Jones & Kus, 2005; Debroy et al., 2009).

Against expe­cta­tion regarding the behaviour of (I) (Toda et al., 1989), growing crystals of diols (II) and (III) from ethanol yields solvent-free crystals. Although both diol molecules crystallize in the triclinic crystal system (space group P1), in the crystal structure of (II) the molecule is located on a general position (Fig. 1a), whereas in (III) the two independent molecules within the unit cell display crystallographic inversion symmetry (Fig. 1b).

The crystal structures lack strong inter­molecular hydrogen bonding, possibly because of the steric shielding of the OH groups by the terminal arene rings. Instead, the hy­droxy H atoms are involved in intra­molecular O—H···π contacts (Desiraju & Steiner, 1999), with the central ring of the terphenyl unit acting as an acceptor. The O—H···centroid distances of these inter­actions are 2.66 and 3.00 Å in (II), and 2.63 and 2.67 Å in (III). Unlike diol (II), the crystal structure of which is stabilized by a three-dimensional network of C—H···π hydrogen bonds (Nishio, 2004; H···centroid = 2.63 and 2.67 Å) (Fig. 2a), the crystal structure of (III) is composed of infinite strands of C—H···O hydrogen-bonded molecules (Desiraju & Steiner, 1999) (H···O = 2.46 and 2.58 Å) (Fig. 2b). Weak noncovalent inter­actions of the C—H···π type inter­connect the molecular chains.

A comparison of the molecular structures of (II) and the corresponding bi­phenyl-based compound (I) (Skobridis et al., 2011) reveals that, in the latter case, the decreased separation of the hy­droxy groups enables intra­molecular O—H···O hydrogen bonding, which requires a syn orientation of the hy­droxy groups and a nearly orthogonal arrangement of the bi­phenyl rings. The second OH H atom participates in the formation of a weak intra­molecular O—H···π contact, with one ring of the bi­phenyl element acting as an acceptor. Unlike (II), in the crystal structure of (I) molecules are connected via C—H···O hydrogen bonding into one-dimensional supra­molecular aggregates.

Growing crystals of the diols from di­methyl­formamide gives a monosolvate in both cases, denoted (IIa) and (IIIa), respectively. Although a statistical analysis of the E values of (IIa) suggests crystallographic centrosymmetry, a conclusive structure model was found in the space group P1, with one diol molecule and one molecule of solvent in the unit cell (Fig. 1c). Obviously, the host molecules form a lattice exhibiting centrosymmetry, which is disturbed by the disordered solvent molecule. Inclusion compound (IIIa) crystallizes in the space group P1, with the asymmetric part of the unit cell containing one diol molecule and one solvent molecule, the latter disordered over two positions (site-occupancy factors = 0.71 and 0.29) (Fig. 1d). Both crystal structures are constructed of the same kind of supra­molecular strands with alternating host and guest molecules (Figs. 3a and 3b). According to the given host–guest stoichiometric ratio, the O atom of the solvent molecule acts as a bifurcated acceptor. Nevertheless, the chain structures reveal marked differences. As is obvious from the chain structure of (IIa) (Fig. 3a), the formyl H atom of the solvent molecule participates in a C—H···π inter­action.

The steric demand of an additional ring substituent in (IIIa) increases the distance between host molecules within a given strand [11.02 (1) versus 9.67 (2) Å], thus preventing this kind of host–guest inter­action (Fig. 3b). No directed noncovalent bonds are observed between the molecules of neighbouring strands, so that inter­strand association appears to be restricted to van der Waals forces. In an analogous way to the solvent-free crystals, the hy­droxy H atoms of the host molecule in inclusion structure (IIIb) (space group P1) are involved in the formation of intra­molecular O—H···π hydrogen bonding (Fig. 1e). The host lattice is constructed of strands of C—H···O hydrogen-bonded molecules, which are further assembled into layered substructures which include channel-like voids extending in the direction of the crystallographic a axis (Fig. 3c). These lattice voids are occupied by dimers of C—H···N hydrogen-bonded solvent molecules with the graph-set descriptor R₂²(8) (Etter et al., 1990; Bernstein et al., 1995).

In conclusion, it can be said that the solvent-free crystals of (II) and (III) reveal structural similarities. The steric shielding by terminal aromatic groups prevents molecular association by conventional hydrogen bonding. Hence, the OH H atoms are involved in intra­molecular O—H···π contacts, leading to the formation of a three-dimensional network of weakly associated molecules. The presence of a solvent with distinct acceptor ability, as in (IIa) and (IIIa), favours the formation of strands of O—H···O hydrogen-bonded host and guest molecules. On the other hand, the moderate acceptor character of the solvent species in (IIIb) induces the formation of a host lattice with a channel-like cavity structure incorporating the solvent molecules.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-NT (Sheldrick, 2008); data reduction: SAINT-NT (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. Perspective views of the molecular structures of unsolvated diols (a) (II) and (b) (III), and inclusion structures (c) (IIa), (d) (IIIa) and (e) (IIIb), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines represent hydrogen bonds and double-dashed lines represent O—H···π contacts.
	Fig. 2. Packing excerpts for unsolvated diols (a) (II) and (b) (III). Dashed lines represent hydrogen bonds and double-dashed lines represent O—H···π and C—H···π interactions.
	Fig. 3. Packing excerpts for inclusion structures (a) (IIa), (b) (IIIa) and (c) (IIIb). Dashed lines represent hydrogen bonds and double-dashed lines represent C—H···π interactions.

(II) 2,2''-Bis(hydroxydiphenylmethyl)-1,1':4',1''-terphenyl

Crystal data

C44H34O2	Z = 2
Mr = 594.71	F(000) = 628
Triclinic, P1	Dx = 1.237 Mg m^−3
a = 10.7466 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7589 (3) Å	Cell parameters from 7183 reflections
c = 15.0842 (4) Å	θ = 2.5–28.1°
α = 103.436 (2)°	µ = 0.07 mm^−1
β = 93.315 (2)°	T = 100 K
γ = 108.019 (2)°	Plate, colourless
V = 1597.19 (8) Å^3	0.42 × 0.21 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	Rint = 0.037
φ and ω scans	θmax = 27.1°, θmin = 1.4°
24937 measured reflections	h = −13→13
6897 independent reflections	k = −13→13
4770 reflections with I > 2σ(I)	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 0.7053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
6897 reflections	Δρmax = 0.30 e Å^−3
417 parameters	Δρmin = −0.40 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.91912 (11)	0.02680 (12)	0.37774 (8)	0.0227 (3)
H1	0.9519	0.0880	0.3516	0.034*
O2	1.06975 (12)	0.47170 (12)	0.08365 (8)	0.0265 (3)
H2	1.0266	0.4190	0.1128	0.040*
C1	0.78357 (16)	−0.04444 (16)	0.33815 (11)	0.0205 (3)
C2	0.73848 (16)	−0.15549 (17)	0.38928 (11)	0.0202 (3)
C3	0.79737 (17)	−0.13275 (18)	0.47891 (11)	0.0230 (4)
H3	0.8625	−0.0480	0.5088	0.028*
C4	0.76111 (18)	−0.23379 (19)	0.52465 (12)	0.0270 (4)
H4	0.8019	−0.2177	0.5857	0.032*
C5	0.66618 (18)	−0.35769 (18)	0.48222 (12)	0.0284 (4)
H5	0.6430	−0.4269	0.5136	0.034*
C6	0.60540 (19)	−0.38014 (19)	0.39405 (13)	0.0297 (4)
H6	0.5386	−0.4641	0.3650	0.036*
C7	0.64235 (18)	−0.27933 (18)	0.34790 (12)	0.0260 (4)
H7	0.6010	−0.2957	0.2870	0.031*
C8	0.77499 (17)	−0.10848 (16)	0.23483 (11)	0.0219 (4)
C9	0.88058 (19)	−0.14266 (18)	0.20119 (12)	0.0269 (4)
H9	0.9570	−0.1278	0.2425	0.032*
C10	0.8760 (2)	−0.19838 (19)	0.10776 (13)	0.0325 (4)
H10	0.9492	−0.2211	0.0854	0.039*
C11	0.7645 (2)	−0.22083 (19)	0.04717 (12)	0.0322 (4)
H11	0.7614	−0.2581	−0.0169	0.039*
C12	0.65801 (19)	−0.18887 (18)	0.08016 (12)	0.0285 (4)
H12	0.5812	−0.2051	0.0388	0.034*
C13	0.66266 (18)	−0.13312 (17)	0.17361 (12)	0.0244 (4)
H13	0.5889	−0.1117	0.1959	0.029*
C14	0.70294 (17)	0.05302 (17)	0.35398 (11)	0.0207 (4)
C15	0.57926 (17)	0.01426 (18)	0.38313 (11)	0.0241 (4)
H15	0.5456	−0.0729	0.3938	0.029*
C16	0.50381 (18)	0.09926 (19)	0.39705 (13)	0.0292 (4)
H16	0.4192	0.0696	0.4159	0.035*
C17	0.55221 (19)	0.2270 (2)	0.38345 (14)	0.0329 (4)
H17	0.5019	0.2864	0.3939	0.040*
C18	0.67478 (19)	0.2679 (2)	0.35452 (13)	0.0311 (4)
H18	0.7082	0.3562	0.3458	0.037*
C19	0.75041 (17)	0.18251 (18)	0.33785 (11)	0.0233 (4)
C20	0.87891 (17)	0.23605 (17)	0.30277 (12)	0.0226 (4)
C21	0.89420 (18)	0.18678 (18)	0.21163 (12)	0.0252 (4)
H21	0.8228	0.1168	0.1712	0.030*
C22	1.01248 (18)	0.23859 (18)	0.17909 (12)	0.0252 (4)
H22	1.0209	0.2039	0.1166	0.030*
C23	1.11846 (17)	0.34044 (17)	0.23674 (11)	0.0215 (4)
C24	1.10365 (17)	0.38995 (17)	0.32805 (11)	0.0235 (4)
H24	1.1755	0.4592	0.3686	0.028*
C25	0.98506 (18)	0.33920 (17)	0.36036 (12)	0.0245 (4)
H25	0.9761	0.3752	0.4225	0.029*
C26	1.24778 (17)	0.38965 (17)	0.20218 (11)	0.0219 (4)
C27	1.33664 (18)	0.32134 (18)	0.21158 (12)	0.0260 (4)
H27	1.3133	0.2493	0.2405	0.031*
C28	1.45814 (18)	0.35536 (19)	0.18003 (12)	0.0278 (4)
H28	1.5169	0.3068	0.1867	0.033*
C29	1.49255 (18)	0.46071 (18)	0.13877 (12)	0.0263 (4)
H29	1.5758	0.4858	0.1173	0.032*
C30	1.40527 (17)	0.52982 (17)	0.12870 (11)	0.0231 (4)
H30	1.4302	0.6024	0.1004	0.028*
C31	1.28224 (16)	0.49606 (16)	0.15881 (11)	0.0205 (3)
C32	1.18414 (16)	0.57055 (17)	0.14361 (11)	0.0215 (4)
C33	1.23820 (17)	0.67885 (17)	0.09180 (12)	0.0230 (4)
C34	1.24034 (17)	0.63633 (19)	−0.00253 (12)	0.0258 (4)
H34	1.2107	0.5422	−0.0326	0.031*
C35	1.28534 (18)	0.7300 (2)	−0.05295 (13)	0.0304 (4)
H35	1.2846	0.6997	−0.1174	0.036*
C36	1.33125 (19)	0.8669 (2)	−0.00979 (14)	0.0357 (5)
H36	1.3632	0.9309	−0.0443	0.043*
C37	1.3304 (2)	0.9102 (2)	0.08324 (15)	0.0381 (5)
H37	1.3620	1.0044	0.1131	0.046*
C38	1.28361 (19)	0.81697 (18)	0.13414 (14)	0.0314 (4)
H38	1.2827	0.8481	0.1983	0.038*
C39	1.14709 (18)	0.63143 (17)	0.23614 (12)	0.0237 (4)
C40	1.24512 (19)	0.70117 (18)	0.31144 (12)	0.0289 (4)
H40	1.3347	0.7105	0.3050	0.035*
C41	1.2132 (2)	0.75716 (19)	0.39576 (13)	0.0346 (5)
H41	1.2810	0.8052	0.4465	0.042*
C42	1.0828 (2)	0.7434 (2)	0.40627 (14)	0.0360 (5)
H42	1.0609	0.7818	0.4641	0.043*
C43	0.9852 (2)	0.6737 (2)	0.33233 (14)	0.0356 (5)
H43	0.8955	0.6631	0.3395	0.043*
C44	1.01695 (19)	0.61857 (19)	0.24721 (13)	0.0288 (4)
H44	0.9490	0.5719	0.1964	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0206 (6)	0.0248 (6)	0.0244 (6)	0.0062 (5)	0.0027 (5)	0.0120 (5)
O2	0.0228 (6)	0.0298 (7)	0.0246 (6)	0.0023 (5)	0.0017 (5)	0.0124 (5)
C1	0.0209 (9)	0.0226 (8)	0.0197 (8)	0.0075 (7)	0.0026 (7)	0.0085 (7)
C2	0.0204 (8)	0.0238 (8)	0.0210 (8)	0.0108 (7)	0.0063 (7)	0.0094 (7)
C3	0.0240 (9)	0.0262 (9)	0.0216 (9)	0.0105 (7)	0.0043 (7)	0.0084 (7)
C4	0.0286 (10)	0.0354 (10)	0.0241 (9)	0.0150 (8)	0.0058 (7)	0.0149 (8)
C5	0.0333 (10)	0.0295 (9)	0.0304 (10)	0.0132 (8)	0.0114 (8)	0.0178 (8)
C6	0.0320 (10)	0.0259 (9)	0.0308 (10)	0.0063 (8)	0.0068 (8)	0.0106 (8)
C7	0.0279 (10)	0.0282 (9)	0.0221 (9)	0.0076 (8)	0.0030 (7)	0.0092 (7)
C8	0.0282 (9)	0.0195 (8)	0.0209 (8)	0.0082 (7)	0.0059 (7)	0.0100 (7)
C9	0.0321 (10)	0.0295 (9)	0.0251 (9)	0.0141 (8)	0.0069 (8)	0.0123 (8)
C10	0.0409 (11)	0.0348 (10)	0.0289 (10)	0.0190 (9)	0.0143 (9)	0.0109 (8)
C11	0.0481 (12)	0.0281 (9)	0.0186 (9)	0.0097 (9)	0.0078 (8)	0.0063 (7)
C12	0.0338 (10)	0.0263 (9)	0.0224 (9)	0.0042 (8)	0.0009 (8)	0.0091 (7)
C13	0.0257 (9)	0.0255 (9)	0.0232 (9)	0.0069 (7)	0.0048 (7)	0.0102 (7)
C14	0.0233 (9)	0.0255 (8)	0.0154 (8)	0.0096 (7)	0.0026 (6)	0.0076 (7)
C15	0.0255 (9)	0.0281 (9)	0.0216 (9)	0.0096 (7)	0.0044 (7)	0.0110 (7)
C16	0.0259 (10)	0.0393 (10)	0.0300 (10)	0.0151 (8)	0.0101 (8)	0.0163 (8)
C17	0.0346 (11)	0.0405 (11)	0.0379 (11)	0.0234 (9)	0.0143 (9)	0.0200 (9)
C18	0.0358 (11)	0.0318 (10)	0.0362 (11)	0.0166 (9)	0.0125 (8)	0.0196 (8)
C19	0.0257 (9)	0.0290 (9)	0.0201 (8)	0.0119 (8)	0.0056 (7)	0.0114 (7)
C20	0.0266 (9)	0.0249 (8)	0.0255 (9)	0.0134 (7)	0.0076 (7)	0.0164 (7)
C21	0.0273 (9)	0.0261 (9)	0.0229 (9)	0.0058 (7)	0.0020 (7)	0.0120 (7)
C22	0.0318 (10)	0.0284 (9)	0.0166 (8)	0.0083 (8)	0.0061 (7)	0.0100 (7)
C23	0.0262 (9)	0.0229 (8)	0.0213 (8)	0.0111 (7)	0.0058 (7)	0.0124 (7)
C24	0.0279 (9)	0.0224 (8)	0.0216 (8)	0.0073 (7)	0.0027 (7)	0.0101 (7)
C25	0.0344 (10)	0.0244 (9)	0.0203 (8)	0.0132 (8)	0.0090 (7)	0.0105 (7)
C26	0.0248 (9)	0.0242 (8)	0.0165 (8)	0.0077 (7)	0.0021 (7)	0.0058 (7)
C27	0.0311 (10)	0.0297 (9)	0.0227 (9)	0.0126 (8)	0.0058 (7)	0.0131 (7)
C28	0.0282 (10)	0.0347 (10)	0.0255 (9)	0.0167 (8)	0.0040 (8)	0.0089 (8)
C29	0.0227 (9)	0.0333 (10)	0.0229 (9)	0.0094 (8)	0.0052 (7)	0.0070 (7)
C30	0.0241 (9)	0.0240 (8)	0.0203 (8)	0.0059 (7)	0.0032 (7)	0.0070 (7)
C31	0.0222 (9)	0.0215 (8)	0.0166 (8)	0.0061 (7)	0.0027 (6)	0.0042 (6)
C32	0.0208 (9)	0.0217 (8)	0.0227 (8)	0.0064 (7)	0.0039 (7)	0.0081 (7)
C33	0.0204 (9)	0.0258 (9)	0.0273 (9)	0.0092 (7)	0.0043 (7)	0.0130 (7)
C34	0.0217 (9)	0.0307 (9)	0.0286 (9)	0.0097 (8)	0.0051 (7)	0.0129 (8)
C35	0.0261 (10)	0.0432 (11)	0.0296 (10)	0.0138 (8)	0.0061 (8)	0.0205 (9)
C36	0.0308 (11)	0.0380 (11)	0.0459 (12)	0.0092 (9)	0.0065 (9)	0.0286 (10)
C37	0.0416 (12)	0.0269 (10)	0.0478 (13)	0.0079 (9)	0.0062 (10)	0.0181 (9)
C38	0.0360 (11)	0.0263 (9)	0.0334 (10)	0.0089 (8)	0.0073 (8)	0.0118 (8)
C39	0.0288 (9)	0.0222 (8)	0.0261 (9)	0.0115 (7)	0.0082 (7)	0.0124 (7)
C40	0.0320 (10)	0.0249 (9)	0.0285 (9)	0.0070 (8)	0.0085 (8)	0.0073 (7)
C41	0.0478 (13)	0.0268 (9)	0.0284 (10)	0.0105 (9)	0.0092 (9)	0.0071 (8)
C42	0.0583 (14)	0.0310 (10)	0.0304 (10)	0.0243 (10)	0.0218 (10)	0.0139 (8)
C43	0.0422 (12)	0.0422 (11)	0.0409 (12)	0.0277 (10)	0.0212 (10)	0.0236 (10)
C44	0.0331 (10)	0.0340 (10)	0.0302 (10)	0.0189 (8)	0.0087 (8)	0.0174 (8)

Geometric parameters (Å, º)

O1—C1	1.436 (2)	C21—H21	0.9500
O1—H1	0.8400	C22—C23	1.387 (2)
O2—C32	1.441 (2)	C22—H22	0.9500
O2—H2	0.8400	C23—C24	1.394 (2)
C1—C8	1.535 (2)	C23—C26	1.497 (2)
C1—C2	1.540 (2)	C24—C25	1.387 (2)
C1—C14	1.542 (2)	C24—H24	0.9500
C2—C7	1.385 (2)	C25—H25	0.9500
C2—C3	1.393 (2)	C26—C27	1.392 (2)
C3—C4	1.388 (2)	C26—C31	1.411 (2)
C3—H3	0.9500	C27—C28	1.386 (3)
C4—C5	1.383 (3)	C27—H27	0.9500
C4—H4	0.9500	C28—C29	1.380 (2)
C5—C6	1.381 (3)	C28—H28	0.9500
C5—H5	0.9500	C29—C30	1.387 (2)
C6—C7	1.391 (2)	C29—H29	0.9500
C6—H6	0.9500	C30—C31	1.391 (2)
C7—H7	0.9500	C30—H30	0.9500
C8—C9	1.385 (3)	C31—C32	1.545 (2)
C8—C13	1.393 (2)	C32—C39	1.529 (2)
C9—C10	1.389 (3)	C32—C33	1.537 (2)
C9—H9	0.9500	C33—C38	1.389 (2)
C10—C11	1.386 (3)	C33—C34	1.394 (2)
C10—H10	0.9500	C34—C35	1.387 (2)
C11—C12	1.380 (3)	C34—H34	0.9500
C11—H11	0.9500	C35—C36	1.380 (3)
C12—C13	1.389 (2)	C35—H35	0.9500
C12—H12	0.9500	C36—C37	1.374 (3)
C13—H13	0.9500	C36—H36	0.9500
C14—C15	1.394 (2)	C37—C38	1.393 (3)
C14—C19	1.412 (2)	C37—H37	0.9500
C15—C16	1.388 (3)	C38—H38	0.9500
C15—H15	0.9500	C39—C44	1.386 (3)
C16—C17	1.379 (3)	C39—C40	1.393 (3)
C16—H16	0.9500	C40—C41	1.386 (3)
C17—C18	1.384 (3)	C40—H40	0.9500
C17—H17	0.9500	C41—C42	1.385 (3)
C18—C19	1.395 (3)	C41—H41	0.9500
C18—H18	0.9500	C42—C43	1.377 (3)
C19—C20	1.501 (2)	C42—H42	0.9500
C20—C21	1.393 (2)	C43—C44	1.392 (3)
C20—C25	1.393 (2)	C43—H43	0.9500
C21—C22	1.389 (2)	C44—H44	0.9500
C1—O1—H1	109.5	C21—C22—H22	119.6
C32—O2—H2	109.5	C22—C23—C24	118.60 (16)
O1—C1—C8	109.98 (13)	C22—C23—C26	120.12 (15)
O1—C1—C2	103.80 (12)	C24—C23—C26	121.19 (15)
C8—C1—C2	110.30 (13)	C25—C24—C23	120.68 (16)
O1—C1—C14	110.11 (13)	C25—C24—H24	119.7
C8—C1—C14	110.49 (13)	C23—C24—H24	119.7
C2—C1—C14	111.97 (13)	C24—C25—C20	120.79 (16)
C7—C2—C3	118.71 (15)	C24—C25—H25	119.6
C7—C2—C1	121.79 (14)	C20—C25—H25	119.6
C3—C2—C1	119.49 (15)	C27—C26—C31	118.95 (16)
C4—C3—C2	120.11 (16)	C27—C26—C23	116.65 (15)
C4—C3—H3	119.9	C31—C26—C23	124.37 (15)
C2—C3—H3	119.9	C28—C27—C26	121.94 (16)
C5—C4—C3	120.67 (16)	C28—C27—H27	119.0
C5—C4—H4	119.7	C26—C27—H27	119.0
C3—C4—H4	119.7	C29—C28—C27	119.07 (17)
C6—C5—C4	119.60 (16)	C29—C28—H28	120.5
C6—C5—H5	120.2	C27—C28—H28	120.5
C4—C5—H5	120.2	C28—C29—C30	119.81 (16)
C5—C6—C7	119.77 (17)	C28—C29—H29	120.1
C5—C6—H6	120.1	C30—C29—H29	120.1
C7—C6—H6	120.1	C29—C30—C31	121.98 (16)
C2—C7—C6	121.11 (16)	C29—C30—H30	119.0
C2—C7—H7	119.4	C31—C30—H30	119.0
C6—C7—H7	119.4	C30—C31—C26	118.24 (16)
C9—C8—C13	118.93 (16)	C30—C31—C32	121.24 (14)
C9—C8—C1	119.78 (15)	C26—C31—C32	120.52 (15)
C13—C8—C1	121.30 (16)	O2—C32—C39	111.03 (13)
C8—C9—C10	120.78 (17)	O2—C32—C33	105.33 (13)
C8—C9—H9	119.6	C39—C32—C33	111.39 (14)
C10—C9—H9	119.6	O2—C32—C31	106.96 (13)
C11—C10—C9	119.89 (19)	C39—C32—C31	109.60 (13)
C11—C10—H10	120.1	C33—C32—C31	112.38 (14)
C9—C10—H10	120.1	C38—C33—C34	118.40 (16)
C12—C11—C10	119.78 (17)	C38—C33—C32	123.25 (16)
C12—C11—H11	120.1	C34—C33—C32	118.35 (15)
C10—C11—H11	120.1	C35—C34—C33	120.69 (17)
C11—C12—C13	120.31 (17)	C35—C34—H34	119.7
C11—C12—H12	119.8	C33—C34—H34	119.7
C13—C12—H12	119.8	C36—C35—C34	120.26 (18)
C12—C13—C8	120.31 (17)	C36—C35—H35	119.9
C12—C13—H13	119.8	C34—C35—H35	119.9
C8—C13—H13	119.8	C37—C36—C35	119.66 (17)
C15—C14—C19	118.04 (16)	C37—C36—H36	120.2
C15—C14—C1	120.63 (15)	C35—C36—H36	120.2
C19—C14—C1	121.32 (15)	C36—C37—C38	120.44 (19)
C16—C15—C14	121.93 (16)	C36—C37—H37	119.8
C16—C15—H15	119.0	C38—C37—H37	119.8
C14—C15—H15	119.0	C33—C38—C37	120.54 (18)
C17—C16—C15	119.75 (17)	C33—C38—H38	119.7
C17—C16—H16	120.1	C37—C38—H38	119.7
C15—C16—H16	120.1	C44—C39—C40	118.76 (17)
C16—C17—C18	119.42 (18)	C44—C39—C32	121.34 (16)
C16—C17—H17	120.3	C40—C39—C32	119.90 (16)
C18—C17—H17	120.3	C41—C40—C39	120.62 (19)
C17—C18—C19	121.61 (17)	C41—C40—H40	119.7
C17—C18—H18	119.2	C39—C40—H40	119.7
C19—C18—H18	119.2	C42—C41—C40	120.23 (19)
C18—C19—C14	119.21 (16)	C42—C41—H41	119.9
C18—C19—C20	116.67 (15)	C40—C41—H41	119.9
C14—C19—C20	124.12 (15)	C43—C42—C41	119.52 (18)
C21—C20—C25	118.32 (16)	C43—C42—H42	120.2
C21—C20—C19	121.11 (16)	C41—C42—H42	120.2
C25—C20—C19	120.55 (15)	C42—C43—C44	120.46 (19)
C22—C21—C20	120.85 (16)	C42—C43—H43	119.8
C22—C21—H21	119.6	C44—C43—H43	119.8
C20—C21—H21	119.6	C39—C44—C43	120.42 (18)
C23—C22—C21	120.75 (16)	C39—C44—H44	119.8
C23—C22—H22	119.6	C43—C44—H44	119.8
O1—C1—C2—C7	−149.79 (16)	C22—C23—C24—C25	−0.5 (2)
C8—C1—C2—C7	−32.0 (2)	C26—C23—C24—C25	−177.08 (15)
C14—C1—C2—C7	91.47 (19)	C23—C24—C25—C20	1.1 (3)
O1—C1—C2—C3	28.8 (2)	C21—C20—C25—C24	−1.0 (2)
C8—C1—C2—C3	146.61 (16)	C19—C20—C25—C24	−179.38 (15)
C14—C1—C2—C3	−89.91 (18)	C22—C23—C26—C27	−88.5 (2)
C7—C2—C3—C4	1.0 (3)	C24—C23—C26—C27	88.0 (2)
C1—C2—C3—C4	−177.66 (16)	C22—C23—C26—C31	89.3 (2)
C2—C3—C4—C5	−0.2 (3)	C24—C23—C26—C31	−94.2 (2)
C3—C4—C5—C6	−1.1 (3)	C31—C26—C27—C28	0.4 (3)
C4—C5—C6—C7	1.5 (3)	C23—C26—C27—C28	178.33 (16)
C3—C2—C7—C6	−0.5 (3)	C26—C27—C28—C29	0.5 (3)
C1—C2—C7—C6	178.09 (17)	C27—C28—C29—C30	−0.6 (3)
C5—C6—C7—C2	−0.7 (3)	C28—C29—C30—C31	−0.2 (3)
O1—C1—C8—C9	26.9 (2)	C29—C30—C31—C26	1.1 (2)
C2—C1—C8—C9	−87.03 (18)	C29—C30—C31—C32	−177.60 (15)
C14—C1—C8—C9	148.64 (15)	C27—C26—C31—C30	−1.2 (2)
O1—C1—C8—C13	−153.07 (14)	C23—C26—C31—C30	−178.96 (16)
C2—C1—C8—C13	93.03 (18)	C27—C26—C31—C32	177.57 (15)
C14—C1—C8—C13	−31.3 (2)	C23—C26—C31—C32	−0.2 (2)
C13—C8—C9—C10	1.1 (2)	C30—C31—C32—O2	116.19 (16)
C1—C8—C9—C10	−178.80 (15)	C26—C31—C32—O2	−62.51 (18)
C8—C9—C10—C11	−0.3 (3)	C30—C31—C32—C39	−123.35 (16)
C9—C10—C11—C12	−0.6 (3)	C26—C31—C32—C39	57.95 (19)
C10—C11—C12—C13	0.6 (3)	C30—C31—C32—C33	1.1 (2)
C11—C12—C13—C8	0.2 (3)	C26—C31—C32—C33	−177.63 (15)
C9—C8—C13—C12	−1.1 (2)	O2—C32—C33—C38	138.10 (17)
C1—C8—C13—C12	178.82 (15)	C39—C32—C33—C38	17.6 (2)
O1—C1—C14—C15	−135.35 (15)	C31—C32—C33—C38	−105.79 (19)
C8—C1—C14—C15	102.96 (17)	O2—C32—C33—C34	−41.1 (2)
C2—C1—C14—C15	−20.4 (2)	C39—C32—C33—C34	−161.62 (15)
O1—C1—C14—C19	45.9 (2)	C31—C32—C33—C34	74.96 (19)
C8—C1—C14—C19	−75.81 (19)	C38—C33—C34—C35	−0.7 (3)
C2—C1—C14—C19	160.82 (15)	C32—C33—C34—C35	178.54 (16)
C19—C14—C15—C16	−0.5 (2)	C33—C34—C35—C36	1.3 (3)
C1—C14—C15—C16	−179.32 (15)	C34—C35—C36—C37	−0.9 (3)
C14—C15—C16—C17	−1.1 (3)	C35—C36—C37—C38	0.0 (3)
C15—C16—C17—C18	1.1 (3)	C34—C33—C38—C37	−0.2 (3)
C16—C17—C18—C19	0.6 (3)	C32—C33—C38—C37	−179.45 (17)
C17—C18—C19—C14	−2.3 (3)	C36—C37—C38—C33	0.6 (3)
C17—C18—C19—C20	177.39 (17)	O2—C32—C39—C44	−16.5 (2)
C15—C14—C19—C18	2.2 (2)	C33—C32—C39—C44	100.55 (18)
C1—C14—C19—C18	−179.03 (16)	C31—C32—C39—C44	−134.45 (16)
C15—C14—C19—C20	−177.47 (15)	O2—C32—C39—C40	163.33 (14)
C1—C14—C19—C20	1.3 (2)	C33—C32—C39—C40	−79.62 (19)
C18—C19—C20—C21	−107.1 (2)	C31—C32—C39—C40	45.4 (2)
C14—C19—C20—C21	72.5 (2)	C44—C39—C40—C41	−0.3 (3)
C18—C19—C20—C25	71.2 (2)	C32—C39—C40—C41	179.89 (15)
C14—C19—C20—C25	−109.2 (2)	C39—C40—C41—C42	0.5 (3)
C25—C20—C21—C22	0.4 (2)	C40—C41—C42—C43	0.0 (3)
C19—C20—C21—C22	178.70 (16)	C41—C42—C43—C44	−0.7 (3)
C20—C21—C22—C23	0.2 (3)	C40—C39—C44—C43	−0.5 (2)
C21—C22—C23—C24	−0.1 (2)	C32—C39—C44—C43	179.37 (15)
C21—C22—C23—C26	176.45 (16)	C42—C43—C44—C39	1.0 (3)

Hydrogen-bond geometry (Å, º)

Cg3, Cg4 and Cg5 are the centroids of which? rings.

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41···Cg3^i	0.95	2.56	3.407 (2)	149
O1—H1···Cg4	0.84	2.66	3.481 (2)	166
O2—H2···Cg4	0.84	3.00	3.773 (2)	153
C11—H11···Cg5^ii	0.95	2.77	3.622 (2)	150

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

(IIA) 2,2''-Bis(hydroxydiphenylmethyl)-1,1':4',1''-terphenyl dimethylformamide monosolvate

Crystal data

C44H34O2·C3H7NO	Z = 1
Mr = 667.81	F(000) = 354
Triclinic, P1	Dx = 1.262 Mg m^−3
a = 9.1196 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5474 (5) Å	Cell parameters from 9998 reflections
c = 11.9920 (6) Å	θ = 2.5–29.2°
α = 105.682 (2)°	µ = 0.08 mm^−1
β = 90.853 (2)°	T = 100 K
γ = 117.642 (2)°	Plate, colourless
V = 878.39 (8) Å^3	0.40 × 0.25 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	Rint = 0.024
φ and ω scans	θmax = 27.2°, θmin = 2.5°
14831 measured reflections	h = −11→11
6761 independent reflections	k = −12→12
6542 reflections with I > 2σ(I)	l = −15→15

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.070	w = 1/[σ^2(Fo^2) + (0.0657P)^2 + 2.7219P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.200	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.55 e Å^−3
6761 reflections	Δρmin = −0.44 e Å^−3
447 parameters	Absolute structure: Refined as an inversion twin.
3 restraints

Special details

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C14	0.5466 (4)	1.3206 (4)	0.3978 (3)	0.0159 (9)
C15	0.5845 (4)	1.4595 (4)	0.4933 (3)	0.0181 (13)
H15	0.6981	1.5419	0.5235	0.022*
C16	0.4561 (5)	1.4779 (4)	0.5445 (3)	0.0222 (14)
H16	0.4820	1.5729	0.6097	0.027*
C17	0.2898 (4)	1.3573 (5)	0.5002 (4)	0.0223 (14)
H17	0.2021	1.3699	0.5352	0.027*
C18	0.2520 (3)	1.2184 (5)	0.4047 (3)	0.0183 (13)
H18	0.1383	1.1360	0.3744	0.022*
C19	0.3803 (5)	1.2000 (4)	0.3535 (3)	0.0159 (9)
O1	0.6652 (6)	1.2634 (6)	0.2218 (4)	0.0201 (10)
H1	0.6254	1.3190	0.2029	0.030*
O2	−0.1708 (6)	0.5665 (6)	0.0512 (4)	0.0180 (9)
H2	−0.2602	0.5459	0.0785	0.027*
C1	0.6961 (9)	1.3069 (8)	0.3455 (5)	0.0180 (13)
C2	0.7134 (9)	1.1631 (8)	0.3718 (6)	0.0203 (13)
C3	0.7748 (9)	1.0757 (9)	0.2943 (6)	0.0240 (14)
H3	0.8125	1.1077	0.2272	0.029*
C4	0.7825 (9)	0.9408 (9)	0.3131 (7)	0.0277 (16)
H4	0.8209	0.8791	0.2574	0.033*
C5	0.7333 (10)	0.8969 (9)	0.4144 (7)	0.0307 (17)
H5	0.7367	0.8045	0.4274	0.037*
C6	0.6792 (10)	0.9907 (9)	0.4958 (6)	0.0277 (16)
H6	0.6500	0.9648	0.5662	0.033*
C7	0.6678 (8)	1.1211 (8)	0.4747 (5)	0.0200 (13)
H7	0.6289	1.1827	0.5300	0.024*
C8	0.8637 (8)	1.4697 (8)	0.3965 (5)	0.0175 (12)
C9	0.9731 (9)	1.5015 (9)	0.4939 (6)	0.0235 (14)
H9	0.9477	1.4179	0.5304	0.028*
C10	1.1156 (10)	1.6506 (9)	0.5372 (6)	0.0253 (15)
H10	1.1878	1.6695	0.6040	0.030*
C11	1.1582 (9)	1.7764 (9)	0.4858 (7)	0.0275 (15)
H11	1.2574	1.8807	0.5167	0.033*
C12	1.0501 (10)	1.7433 (9)	0.3878 (6)	0.0255 (15)
H12	1.0778	1.8266	0.3506	0.031*
C13	0.9068 (9)	1.5966 (9)	0.3433 (6)	0.0239 (14)
H13	0.8352	1.5787	0.2766	0.029*
C20	0.3174 (8)	1.0506 (7)	0.2427 (5)	0.0148 (12)
C21	0.2056 (8)	1.0361 (7)	0.1521 (6)	0.0174 (12)
H21	0.1772	1.1221	0.1609	0.021*
C22	0.1372 (9)	0.9029 (9)	0.0525 (6)	0.0207 (13)
H22	0.0636	0.8987	−0.0067	0.025*
C23	0.1737 (8)	0.7710 (8)	0.0357 (6)	0.0178 (13)
C24	0.2849 (8)	0.7858 (8)	0.1241 (5)	0.0189 (13)
H24	0.3148	0.7007	0.1141	0.023*
C25	0.3552 (8)	0.9223 (7)	0.2282 (5)	0.0149 (12)
H25	0.4280	0.9264	0.2880	0.018*
C26	0.1134 (7)	0.6249 (7)	−0.0702 (5)	0.0155 (11)
C27	0.2372 (8)	0.5966 (9)	−0.1230 (6)	0.0231 (14)
H27	0.3512	0.6773	−0.0921	0.028*
C28	0.2050 (9)	0.4595 (9)	−0.2167 (6)	0.0263 (15)
H28	0.2947	0.4450	−0.2464	0.032*
C29	0.0416 (9)	0.3442 (8)	−0.2666 (5)	0.0212 (14)
H29	0.0164	0.2493	−0.3317	0.025*
C30	−0.0863 (8)	0.3692 (8)	−0.2197 (5)	0.0192 (13)
H30	−0.1992	0.2898	−0.2549	0.023*
C31	−0.0561 (7)	0.5070 (7)	−0.1225 (5)	0.0144 (11)
C32	−0.2056 (8)	0.5225 (8)	−0.0755 (5)	0.0129 (11)
C33	−0.3673 (8)	0.3537 (8)	−0.1211 (5)	0.0165 (12)
C34	−0.4003 (8)	0.2335 (8)	−0.0682 (5)	0.0174 (12)
H34	−0.3210	0.2556	−0.0047	0.021*
C35	−0.5479 (9)	0.0791 (9)	−0.1054 (6)	0.0239 (14)
H35	−0.5693	−0.0023	−0.0674	0.029*
C36	−0.6629 (10)	0.0478 (9)	−0.1998 (7)	0.0265 (15)
H36	−0.7641	−0.0556	−0.2258	0.032*
C37	−0.6305 (9)	0.1656 (9)	−0.2552 (7)	0.0280 (16)
H37	−0.7086	0.1429	−0.3197	0.034*
C38	−0.4814 (9)	0.3198 (8)	−0.2162 (5)	0.0199 (13)
H38	−0.4588	0.4008	−0.2548	0.024*
C39	−0.2214 (8)	0.6586 (7)	−0.1100 (5)	0.0151 (12)
C40	−0.2860 (9)	0.7511 (8)	−0.0373 (6)	0.0230 (14)
H40	−0.3246	0.7253	0.0315	0.028*
C41	−0.2941 (9)	0.8799 (9)	−0.0648 (7)	0.0260 (15)
H41	−0.3387	0.9410	−0.0149	0.031*
C42	−0.2392 (10)	0.9193 (9)	−0.1622 (7)	0.0301 (16)
H42	−0.2455	1.0078	−0.1797	0.036*
C43	−0.1739 (10)	0.8320 (9)	−0.2362 (6)	0.0250 (15)
H43	−0.1342	0.8613	−0.3037	0.030*
C44	−0.1668 (9)	0.6983 (8)	−0.2106 (6)	0.0228 (14)
H44	−0.1248	0.6360	−0.2622	0.027*
O1A	0.5361 (6)	0.4732 (5)	0.1540 (4)	0.0237 (9)
N1A	0.2660 (8)	0.4201 (8)	0.1447 (5)	0.0182 (10)
C1A	0.3909 (9)	0.4138 (8)	0.0941 (6)	0.0291 (14)
H1A	0.3731	0.3643	0.0115	0.035*
C2A	0.2757 (11)	0.4983 (10)	0.2638 (6)	0.0348 (16)
H2A1	0.3792	0.5204	0.3083	0.052*
H2A2	0.1787	0.4256	0.2933	0.052*
H2A3	0.2759	0.6035	0.2732	0.052*
C3A	0.0924 (10)	0.3371 (9)	0.0707 (7)	0.0360 (16)
H3A1	0.1003	0.3005	−0.0125	0.054*
H3A2	0.0504	0.4169	0.0836	0.054*
H3A3	0.0153	0.2406	0.0937	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C14	0.022 (2)	0.015 (2)	0.0140 (18)	0.0099 (19)	0.0057 (16)	0.0066 (16)
C15	0.021 (4)	0.012 (3)	0.013 (3)	0.005 (3)	−0.001 (2)	0.000 (2)
C16	0.022 (4)	0.021 (3)	0.023 (3)	0.010 (3)	0.005 (3)	0.006 (3)
C17	0.027 (4)	0.025 (3)	0.015 (3)	0.017 (3)	0.005 (3)	0.001 (2)
C18	0.015 (3)	0.016 (3)	0.015 (3)	0.004 (3)	−0.001 (2)	−0.002 (2)
C19	0.022 (2)	0.015 (2)	0.0140 (18)	0.0099 (19)	0.0057 (16)	0.0066 (16)
O1	0.024 (3)	0.022 (2)	0.018 (2)	0.013 (2)	0.0059 (18)	0.0071 (18)
O2	0.016 (2)	0.023 (2)	0.0095 (19)	0.007 (2)	0.0012 (16)	0.0024 (17)
C1	0.017 (3)	0.019 (3)	0.017 (3)	0.007 (3)	0.000 (2)	0.007 (2)
C2	0.016 (3)	0.021 (3)	0.022 (3)	0.009 (3)	0.002 (2)	0.006 (3)
C3	0.020 (3)	0.024 (3)	0.033 (4)	0.014 (3)	0.006 (3)	0.011 (3)
C4	0.026 (4)	0.021 (3)	0.037 (4)	0.015 (3)	0.001 (3)	0.003 (3)
C5	0.029 (4)	0.019 (3)	0.039 (4)	0.010 (3)	−0.006 (3)	0.005 (3)
C6	0.026 (4)	0.023 (4)	0.029 (4)	0.007 (3)	0.000 (3)	0.011 (3)
C7	0.020 (3)	0.019 (3)	0.017 (3)	0.009 (3)	−0.004 (2)	−0.001 (2)
C8	0.020 (3)	0.015 (3)	0.017 (3)	0.008 (3)	0.010 (2)	0.005 (2)
C9	0.023 (4)	0.023 (3)	0.026 (3)	0.014 (3)	0.003 (3)	0.006 (3)
C10	0.024 (4)	0.025 (4)	0.025 (3)	0.013 (3)	0.003 (3)	0.003 (3)
C11	0.016 (4)	0.016 (3)	0.040 (4)	0.002 (3)	0.005 (3)	0.005 (3)
C12	0.029 (4)	0.018 (3)	0.031 (4)	0.013 (3)	0.013 (3)	0.009 (3)
C13	0.020 (4)	0.020 (3)	0.031 (4)	0.008 (3)	0.009 (3)	0.012 (3)
C20	0.013 (3)	0.012 (3)	0.013 (3)	0.004 (2)	0.003 (2)	−0.001 (2)
C21	0.020 (3)	0.011 (3)	0.025 (3)	0.009 (3)	0.005 (2)	0.010 (2)
C22	0.017 (3)	0.027 (4)	0.023 (3)	0.012 (3)	0.006 (3)	0.014 (3)
C23	0.011 (3)	0.015 (3)	0.026 (3)	0.003 (3)	0.004 (2)	0.010 (3)
C24	0.015 (3)	0.017 (3)	0.018 (3)	0.006 (3)	0.002 (2)	−0.001 (2)
C25	0.017 (3)	0.008 (3)	0.015 (3)	0.005 (2)	−0.001 (2)	0.000 (2)
C26	0.012 (3)	0.015 (3)	0.018 (3)	0.007 (2)	0.002 (2)	0.005 (2)
C27	0.015 (3)	0.025 (3)	0.031 (4)	0.009 (3)	0.011 (3)	0.012 (3)
C28	0.017 (4)	0.030 (4)	0.033 (4)	0.013 (3)	0.009 (3)	0.008 (3)
C29	0.027 (4)	0.022 (3)	0.015 (3)	0.016 (3)	0.000 (3)	−0.002 (2)
C30	0.018 (3)	0.022 (3)	0.019 (3)	0.010 (3)	0.006 (2)	0.009 (3)
C31	0.014 (3)	0.014 (3)	0.013 (2)	0.006 (2)	−0.002 (2)	0.002 (2)
C32	0.012 (3)	0.014 (3)	0.010 (3)	0.005 (2)	0.002 (2)	0.003 (2)
C33	0.008 (3)	0.014 (3)	0.020 (3)	0.003 (3)	−0.002 (2)	−0.002 (2)
C34	0.021 (3)	0.019 (3)	0.013 (3)	0.012 (3)	0.004 (2)	0.002 (2)
C35	0.018 (3)	0.016 (3)	0.034 (4)	0.006 (3)	0.007 (3)	0.007 (3)
C36	0.021 (4)	0.017 (3)	0.034 (4)	0.008 (3)	0.003 (3)	−0.001 (3)
C37	0.016 (4)	0.021 (3)	0.034 (4)	0.005 (3)	−0.006 (3)	−0.004 (3)
C38	0.020 (4)	0.018 (3)	0.016 (3)	0.006 (3)	−0.001 (2)	0.002 (2)
C39	0.012 (3)	0.007 (3)	0.016 (3)	0.001 (2)	−0.005 (2)	−0.004 (2)
C40	0.020 (3)	0.017 (3)	0.028 (3)	0.007 (3)	0.003 (3)	0.003 (3)
C41	0.016 (3)	0.018 (3)	0.038 (4)	0.007 (3)	−0.003 (3)	0.003 (3)
C42	0.027 (4)	0.021 (3)	0.047 (4)	0.014 (3)	−0.002 (3)	0.014 (3)
C43	0.026 (4)	0.021 (3)	0.028 (3)	0.011 (3)	−0.002 (3)	0.011 (3)
C44	0.021 (4)	0.016 (3)	0.030 (3)	0.007 (3)	0.002 (3)	0.007 (3)
O1A	0.018 (2)	0.024 (2)	0.024 (2)	0.0081 (19)	0.0049 (17)	0.0040 (17)
N1A	0.018 (3)	0.019 (2)	0.018 (2)	0.010 (2)	0.0010 (19)	0.0058 (17)
C1A	0.035 (4)	0.018 (3)	0.035 (3)	0.013 (3)	0.014 (3)	0.008 (2)
C2A	0.050 (5)	0.042 (4)	0.028 (3)	0.032 (4)	0.014 (3)	0.018 (3)
C3A	0.034 (4)	0.030 (3)	0.038 (4)	0.008 (3)	0.008 (3)	0.015 (3)

Geometric parameters (Å, º)

C14—C15	1.3900	C24—H24	0.9500
C14—C19	1.3900	C25—H25	0.9500
C14—C1	1.555 (7)	C26—C27	1.400 (8)
C15—C16	1.3900	C26—C31	1.423 (8)
C15—H15	0.9500	C27—C28	1.379 (9)
C16—C17	1.3900	C27—H27	0.9500
C16—H16	0.9500	C28—C29	1.373 (9)
C17—C18	1.3900	C28—H28	0.9500
C17—H17	0.9500	C29—C30	1.393 (8)
C18—C19	1.3900	C29—H29	0.9500
C18—H18	0.9500	C30—C31	1.411 (7)
C19—C20	1.524 (6)	C30—H30	0.9500
O1—C1	1.414 (8)	C31—C32	1.538 (8)
O1—H1	0.8400	C32—C39	1.531 (8)
O2—C32	1.450 (7)	C32—C33	1.538 (9)
O2—H2	0.8400	C33—C34	1.375 (9)
C1—C8	1.543 (10)	C33—C38	1.393 (9)
C1—C2	1.563 (9)	C34—C35	1.403 (10)
C2—C3	1.379 (9)	C34—H34	0.9500
C2—C7	1.409 (9)	C35—C36	1.400 (10)
C3—C4	1.397 (9)	C35—H35	0.9500
C3—H3	0.9500	C36—C37	1.376 (11)
C4—C5	1.403 (11)	C36—H36	0.9500
C4—H4	0.9500	C37—C38	1.409 (10)
C5—C6	1.397 (11)	C37—H37	0.9500
C5—H5	0.9500	C38—H38	0.9500
C6—C7	1.383 (9)	C39—C44	1.392 (9)
C6—H6	0.9500	C39—C40	1.403 (9)
C7—H7	0.9500	C40—C41	1.390 (10)
C8—C9	1.395 (10)	C40—H40	0.9500
C8—C13	1.418 (9)	C41—C42	1.354 (11)
C9—C10	1.360 (11)	C41—H41	0.9500
C9—H9	0.9500	C42—C43	1.383 (11)
C10—C11	1.396 (10)	C42—H42	0.9500
C10—H10	0.9500	C43—C44	1.419 (9)
C11—C12	1.389 (11)	C43—H43	0.9500
C11—H11	0.9500	C44—H44	0.9500
C12—C13	1.353 (11)	O1A—C1A	1.283 (8)
C12—H12	0.9500	N1A—C1A	1.317 (9)
C13—H13	0.9500	N1A—C2A	1.401 (9)
C20—C25	1.389 (8)	N1A—C3A	1.528 (9)
C20—C21	1.413 (9)	C1A—H1A	0.9500
C21—C22	1.361 (9)	C2A—H2A1	0.9800
C21—H21	0.9500	C2A—H2A2	0.9800
C22—C23	1.412 (9)	C2A—H2A3	0.9800
C22—H22	0.9500	C3A—H3A1	0.9800
C23—C24	1.388 (9)	C3A—H3A2	0.9800
C23—C26	1.473 (9)	C3A—H3A3	0.9800
C24—C25	1.410 (8)
C15—C14—C19	120.0	C24—C25—H25	120.2
C15—C14—C1	117.4 (3)	C27—C26—C31	116.6 (5)
C19—C14—C1	122.6 (3)	C27—C26—C23	116.1 (5)
C16—C15—C14	120.0	C31—C26—C23	127.3 (5)
C16—C15—H15	120.0	C28—C27—C26	124.5 (6)
C14—C15—H15	120.0	C28—C27—H27	117.8
C15—C16—C17	120.0	C26—C27—H27	117.8
C15—C16—H16	120.0	C29—C28—C27	119.2 (6)
C17—C16—H16	120.0	C29—C28—H28	120.4
C16—C17—C18	120.0	C27—C28—H28	120.4
C16—C17—H17	120.0	C28—C29—C30	118.7 (5)
C18—C17—H17	120.0	C28—C29—H29	120.7
C19—C18—C17	120.0	C30—C29—H29	120.7
C19—C18—H18	120.0	C29—C30—C31	123.0 (5)
C17—C18—H18	120.0	C29—C30—H30	118.5
C18—C19—C14	120.0	C31—C30—H30	118.5
C18—C19—C20	113.4 (3)	C30—C31—C26	118.1 (5)
C14—C19—C20	126.3 (3)	C30—C31—C32	119.4 (5)
C1—O1—H1	109.5	C26—C31—C32	122.6 (5)
C32—O2—H2	109.5	O2—C32—C39	110.4 (5)
O1—C1—C8	110.3 (5)	O2—C32—C31	106.5 (5)
O1—C1—C14	110.0 (5)	C39—C32—C31	109.9 (5)
C8—C1—C14	111.8 (5)	O2—C32—C33	108.1 (5)
O1—C1—C2	105.8 (5)	C39—C32—C33	111.8 (5)
C8—C1—C2	108.3 (5)	C31—C32—C33	110.1 (5)
C14—C1—C2	110.4 (5)	C34—C33—C38	119.1 (6)
C3—C2—C7	118.9 (6)	C34—C33—C32	119.9 (5)
C3—C2—C1	120.2 (6)	C38—C33—C32	121.0 (6)
C7—C2—C1	120.9 (6)	C33—C34—C35	121.7 (6)
C2—C3—C4	121.0 (7)	C33—C34—H34	119.1
C2—C3—H3	119.5	C35—C34—H34	119.1
C4—C3—H3	119.5	C36—C35—C34	118.5 (7)
C3—C4—C5	119.9 (7)	C36—C35—H35	120.7
C3—C4—H4	120.1	C34—C35—H35	120.7
C5—C4—H4	120.1	C37—C36—C35	120.5 (7)
C6—C5—C4	119.1 (7)	C37—C36—H36	119.7
C6—C5—H5	120.4	C35—C36—H36	119.7
C4—C5—H5	120.4	C36—C37—C38	120.0 (7)
C7—C6—C5	120.5 (7)	C36—C37—H37	120.0
C7—C6—H6	119.8	C38—C37—H37	120.0
C5—C6—H6	119.8	C33—C38—C37	120.1 (6)
C6—C7—C2	120.5 (6)	C33—C38—H38	120.0
C6—C7—H7	119.7	C37—C38—H38	120.0
C2—C7—H7	119.7	C44—C39—C40	118.4 (6)
C9—C8—C13	118.0 (7)	C44—C39—C32	121.5 (5)
C9—C8—C1	123.9 (6)	C40—C39—C32	120.1 (6)
C13—C8—C1	118.1 (6)	C41—C40—C39	120.7 (7)
C10—C9—C8	120.8 (7)	C41—C40—H40	119.7
C10—C9—H9	119.6	C39—C40—H40	119.7
C8—C9—H9	119.6	C42—C41—C40	120.7 (7)
C9—C10—C11	121.4 (7)	C42—C41—H41	119.6
C9—C10—H10	119.3	C40—C41—H41	119.6
C11—C10—H10	119.3	C41—C42—C43	120.6 (6)
C12—C11—C10	117.5 (7)	C41—C42—H42	119.7
C12—C11—H11	121.2	C43—C42—H42	119.7
C10—C11—H11	121.2	C42—C43—C44	119.6 (7)
C13—C12—C11	122.3 (7)	C42—C43—H43	120.2
C13—C12—H12	118.9	C44—C43—H43	120.2
C11—C12—H12	118.9	C39—C44—C43	119.9 (6)
C12—C13—C8	119.9 (7)	C39—C44—H44	120.0
C12—C13—H13	120.1	C43—C44—H44	120.0
C8—C13—H13	120.1	C1A—N1A—C2A	125.9 (6)
C25—C20—C21	117.8 (6)	C1A—N1A—C3A	119.3 (6)
C25—C20—C19	124.0 (5)	C2A—N1A—C3A	114.8 (6)
C21—C20—C19	118.2 (5)	O1A—C1A—N1A	121.4 (6)
C22—C21—C20	122.1 (6)	O1A—C1A—H1A	119.3
C22—C21—H21	118.9	N1A—C1A—H1A	119.3
C20—C21—H21	118.9	N1A—C2A—H2A1	109.5
C21—C22—C23	121.2 (6)	N1A—C2A—H2A2	109.5
C21—C22—H22	119.4	H2A1—C2A—H2A2	109.5
C23—C22—H22	119.4	N1A—C2A—H2A3	109.5
C24—C23—C22	116.8 (6)	H2A1—C2A—H2A3	109.5
C24—C23—C26	117.2 (5)	H2A2—C2A—H2A3	109.5
C22—C23—C26	125.9 (6)	N1A—C3A—H3A1	109.5
C23—C24—C25	122.5 (6)	N1A—C3A—H3A2	109.5
C23—C24—H24	118.7	H3A1—C3A—H3A2	109.5
C25—C24—H24	118.7	N1A—C3A—H3A3	109.5
C20—C25—C24	119.6 (6)	H3A1—C3A—H3A3	109.5
C20—C25—H25	120.2	H3A2—C3A—H3A3	109.5
C19—C14—C15—C16	0.0	C26—C23—C24—C25	178.1 (6)
C1—C14—C15—C16	−179.4 (4)	C21—C20—C25—C24	1.4 (9)
C14—C15—C16—C17	0.0	C19—C20—C25—C24	177.3 (5)
C15—C16—C17—C18	0.0	C23—C24—C25—C20	−2.1 (10)
C16—C17—C18—C19	0.0	C24—C23—C26—C27	−51.2 (8)
C17—C18—C19—C14	0.0	C22—C23—C26—C27	124.4 (7)
C17—C18—C19—C20	−174.2 (4)	C24—C23—C26—C31	126.6 (7)
C15—C14—C19—C18	0.0	C22—C23—C26—C31	−57.7 (9)
C1—C14—C19—C18	179.4 (4)	C31—C26—C27—C28	−3.5 (9)
C15—C14—C19—C20	173.4 (5)	C23—C26—C27—C28	174.5 (6)
C1—C14—C19—C20	−7.2 (5)	C26—C27—C28—C29	2.8 (10)
C15—C14—C1—O1	−133.3 (4)	C27—C28—C29—C30	−0.6 (9)
C19—C14—C1—O1	47.3 (6)	C28—C29—C30—C31	−0.6 (9)
C15—C14—C1—C8	−10.4 (6)	C29—C30—C31—C26	−0.2 (8)
C19—C14—C1—C8	170.2 (4)	C29—C30—C31—C32	−178.9 (5)
C15—C14—C1—C2	110.3 (5)	C27—C26—C31—C30	2.1 (7)
C19—C14—C1—C2	−69.2 (5)	C23—C26—C31—C30	−175.7 (6)
O1—C1—C2—C3	30.2 (9)	C27—C26—C31—C32	−179.2 (5)
C8—C1—C2—C3	−88.1 (8)	C23—C26—C31—C32	2.9 (9)
C14—C1—C2—C3	149.1 (6)	C30—C31—C32—O2	134.4 (5)
O1—C1—C2—C7	−150.2 (6)	C26—C31—C32—O2	−44.3 (7)
C8—C1—C2—C7	91.5 (7)	C30—C31—C32—C39	−106.1 (6)
C14—C1—C2—C7	−31.2 (8)	C26—C31—C32—C39	75.3 (6)
C7—C2—C3—C4	3.9 (11)	C30—C31—C32—C33	17.4 (7)
C1—C2—C3—C4	−176.4 (6)	C26—C31—C32—C33	−161.2 (5)
C2—C3—C4—C5	−2.5 (11)	O2—C32—C33—C34	−36.2 (7)
C3—C4—C5—C6	−0.8 (11)	C39—C32—C33—C34	−157.8 (6)
C4—C5—C6—C7	2.6 (12)	C31—C32—C33—C34	79.8 (7)
C5—C6—C7—C2	−1.1 (11)	O2—C32—C33—C38	144.1 (6)
C3—C2—C7—C6	−2.1 (10)	C39—C32—C33—C38	22.5 (8)
C1—C2—C7—C6	178.2 (6)	C31—C32—C33—C38	−99.9 (6)
O1—C1—C8—C9	−144.3 (6)	C38—C33—C34—C35	−1.6 (10)
C14—C1—C8—C9	92.9 (7)	C32—C33—C34—C35	178.6 (6)
C2—C1—C8—C9	−29.0 (9)	C33—C34—C35—C36	0.6 (10)
O1—C1—C8—C13	37.6 (8)	C34—C35—C36—C37	0.6 (11)
C14—C1—C8—C13	−85.2 (7)	C35—C36—C37—C38	−0.7 (11)
C2—C1—C8—C13	152.9 (6)	C34—C33—C38—C37	1.6 (10)
C13—C8—C9—C10	0.8 (10)	C32—C33—C38—C37	−178.7 (6)
C1—C8—C9—C10	−177.3 (6)	C36—C37—C38—C33	−0.4 (11)
C8—C9—C10—C11	−0.4 (11)	O2—C32—C39—C44	145.3 (6)
C9—C10—C11—C12	−0.5 (11)	C31—C32—C39—C44	28.1 (8)
C10—C11—C12—C13	1.1 (11)	C33—C32—C39—C44	−94.4 (7)
C11—C12—C13—C8	−0.7 (11)	O2—C32—C39—C40	−32.2 (8)
C9—C8—C13—C12	−0.3 (10)	C31—C32—C39—C40	−149.4 (6)
C1—C8—C13—C12	177.9 (6)	C33—C32—C39—C40	88.1 (7)
C18—C19—C20—C25	−122.3 (6)	C44—C39—C40—C41	−0.4 (10)
C14—C19—C20—C25	63.9 (7)	C32—C39—C40—C41	177.1 (6)
C18—C19—C20—C21	53.6 (6)	C39—C40—C41—C42	−0.3 (11)
C14—C19—C20—C21	−120.2 (5)	C40—C41—C42—C43	0.0 (12)
C25—C20—C21—C22	−0.7 (9)	C41—C42—C43—C44	0.9 (11)
C19—C20—C21—C22	−176.9 (6)	C40—C39—C44—C43	1.4 (10)
C20—C21—C22—C23	0.7 (10)	C32—C39—C44—C43	−176.1 (6)
C21—C22—C23—C24	−1.4 (9)	C42—C43—C44—C39	−1.6 (10)
C21—C22—C23—C26	−177.0 (6)	C2A—N1A—C1A—O1A	4.4 (10)
C22—C23—C24—C25	2.1 (9)	C3A—N1A—C1A—O1A	−175.8 (6)

Hydrogen-bond geometry (Å, º)

Cg6 is the centroid of which? ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1A^i	0.84	1.99	2.818 (6)	171
O1—H1···O1A^ii	0.84	2.18	3.016 (6)	177
C1A—H1A···Cg6^iii	0.95	2.75	3.548 (7)	142

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

(III) 2,2''-Bis[hydroxybis(4-methylphenyl)methyl]-1,1':4',1''-terphenyl

Crystal data

C48H42O2	Z = 2
Mr = 650.81	F(000) = 692
Triclinic, P1	Dx = 1.182 Mg m^−3
a = 9.4052 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1823 (5) Å	Cell parameters from 5022 reflections
c = 15.6828 (5) Å	θ = 2.3–25.6°
α = 79.371 (2)°	µ = 0.07 mm^−1
β = 80.965 (2)°	T = 100 K
γ = 74.371 (2)°	Irregular, colourless
V = 1828.49 (11) Å^3	0.23 × 0.15 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	Rint = 0.035
φ and ω scans	θmax = 26.5°, θmin = 1.9°
27235 measured reflections	h = −10→11
7496 independent reflections	k = −15→16
4769 reflections with I > 2σ(I)	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.4621P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
7496 reflections	Δρmax = 0.17 e Å^−3
457 parameters	Δρmin = −0.19 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.46253 (13)	0.81994 (10)	0.37665 (9)	0.0421 (3)
H1	0.4606	0.8565	0.4156	0.063*
C1	0.6109 (2)	0.75530 (14)	0.35921 (12)	0.0315 (4)
C2	0.6581 (2)	0.67992 (13)	0.44188 (11)	0.0295 (4)
C3	0.5549 (2)	0.63118 (14)	0.49536 (12)	0.0363 (5)
H3	0.4566	0.6460	0.4802	0.044*
C4	0.5937 (2)	0.56150 (15)	0.57010 (12)	0.0414 (5)
H4	0.5213	0.5293	0.6055	0.050*
C5	0.7355 (2)	0.53737 (14)	0.59473 (12)	0.0389 (5)
C6	0.8379 (2)	0.58572 (14)	0.54134 (12)	0.0383 (5)
H6	0.9359	0.5711	0.5567	0.046*
C7	0.8002 (2)	0.65489 (14)	0.46599 (12)	0.0360 (5)
H7	0.8735	0.6858	0.4301	0.043*
C8	0.7755 (3)	0.46220 (17)	0.67661 (13)	0.0572 (6)
H8A	0.7359	0.4991	0.7274	0.086*
H8B	0.8839	0.4375	0.6744	0.086*
H8C	0.7329	0.4010	0.6815	0.086*
C9	0.5964 (2)	0.69198 (15)	0.29003 (12)	0.0342 (4)
C10	0.6836 (2)	0.58956 (15)	0.28419 (12)	0.0356 (5)
H10	0.7518	0.5562	0.3257	0.043*
C11	0.6728 (2)	0.53532 (17)	0.21872 (12)	0.0428 (5)
H11	0.7339	0.4655	0.2159	0.051*
C12	0.5739 (3)	0.58153 (19)	0.15725 (13)	0.0493 (6)
C13	0.4858 (3)	0.68333 (19)	0.16402 (14)	0.0544 (6)
H13	0.4164	0.7161	0.1230	0.065*
C14	0.4963 (2)	0.73828 (17)	0.22894 (13)	0.0462 (5)
H14	0.4349	0.8080	0.2318	0.055*
C15	0.5611 (3)	0.5237 (2)	0.08600 (14)	0.0688 (8)
H15A	0.4853	0.4834	0.1059	0.103*
H15B	0.6570	0.4745	0.0714	0.103*
H15C	0.5328	0.5752	0.0342	0.103*
C16	0.72108 (19)	0.82580 (13)	0.32426 (12)	0.0315 (4)
C17	0.8291 (2)	0.79901 (14)	0.25521 (12)	0.0362 (5)
H17	0.8304	0.7396	0.2285	0.043*
C18	0.9350 (2)	0.85678 (15)	0.22421 (13)	0.0404 (5)
H18	1.0085	0.8361	0.1775	0.049*
C19	0.9334 (2)	0.94382 (15)	0.26115 (13)	0.0403 (5)
H19	1.0060	0.9834	0.2406	0.048*
C20	0.8252 (2)	0.97302 (14)	0.32838 (13)	0.0371 (5)
H20	0.8225	1.0344	0.3528	0.044*
C21	0.7191 (2)	0.91495 (13)	0.36179 (12)	0.0317 (4)
C22	0.6070 (2)	0.95621 (13)	0.43400 (12)	0.0333 (4)
C23	0.5055 (2)	1.05419 (14)	0.41615 (12)	0.0356 (5)
H23	0.5086	1.0923	0.3585	0.043*
C24	0.4008 (2)	1.09687 (14)	0.48042 (12)	0.0353 (5)
H24	0.3327	1.1636	0.4662	0.042*
O1A	0.22765 (14)	0.04781 (9)	0.17701 (8)	0.0355 (3)
H1A	0.2817	0.0315	0.1312	0.053*
C1A	0.2079 (2)	0.15963 (13)	0.17983 (11)	0.0305 (4)
C2A	0.1114 (2)	0.17657 (14)	0.26677 (11)	0.0313 (4)
C3A	0.1427 (2)	0.10060 (15)	0.34002 (12)	0.0365 (5)
H3A	0.2185	0.0370	0.3346	0.044*
C4A	0.0644 (2)	0.11686 (16)	0.42067 (12)	0.0390 (5)
H4A	0.0876	0.0638	0.4698	0.047*
C5A	−0.0471 (2)	0.20845 (17)	0.43190 (12)	0.0390 (5)
C6A	−0.0798 (2)	0.28275 (16)	0.35849 (12)	0.0418 (5)
H6A	−0.1571	0.3455	0.3638	0.050*
C7A	−0.0016 (2)	0.26734 (15)	0.27698 (12)	0.0370 (5)
H7A	−0.0261	0.3198	0.2276	0.044*
C8A	−0.1283 (2)	0.22613 (19)	0.52102 (13)	0.0531 (6)
H8A1	−0.2139	0.1947	0.5318	0.080*
H8A2	−0.1627	0.3028	0.5234	0.080*
H8A3	−0.0610	0.1925	0.5656	0.080*
C9A	0.1282 (2)	0.22560 (14)	0.10223 (11)	0.0303 (4)
C10A	0.0182 (2)	0.19215 (16)	0.07397 (12)	0.0404 (5)
H10A	−0.0081	0.1290	0.1036	0.048*
C11A	−0.0538 (2)	0.24967 (17)	0.00310 (12)	0.0448 (5)
H11A	−0.1289	0.2252	−0.0149	0.054*
C12A	−0.0188 (2)	0.34180 (15)	−0.04204 (12)	0.0380 (5)
C13A	0.0902 (2)	0.37525 (15)	−0.01358 (12)	0.0381 (5)
H13A	0.1167	0.4382	−0.0435	0.046*
C14A	0.1617 (2)	0.31889 (14)	0.05771 (12)	0.0349 (4)
H14A	0.2350	0.3446	0.0765	0.042*
C15A	−0.0973 (3)	0.40358 (17)	−0.11901 (13)	0.0506 (6)
H15D	−0.1250	0.3544	−0.1495	0.076*
H15E	−0.0311	0.4415	−0.1590	0.076*
H15F	−0.1869	0.4551	−0.0987	0.076*
C16A	0.3593 (2)	0.18454 (13)	0.17946 (11)	0.0293 (4)
C17A	0.3713 (2)	0.25416 (14)	0.23326 (12)	0.0341 (4)
H17A	0.2851	0.2867	0.2683	0.041*
C18A	0.5047 (2)	0.27739 (15)	0.23729 (12)	0.0379 (5)
H18A	0.5090	0.3264	0.2737	0.045*
C19A	0.6310 (2)	0.22941 (15)	0.18863 (13)	0.0412 (5)
H19A	0.7238	0.2428	0.1927	0.049*
C20A	0.6214 (2)	0.16136 (15)	0.13367 (12)	0.0367 (5)
H20A	0.7090	0.1282	0.1001	0.044*
C21A	0.4870 (2)	0.13999 (13)	0.12606 (11)	0.0283 (4)
C22A	0.49112 (19)	0.06817 (13)	0.06144 (11)	0.0267 (4)
C23A	0.57056 (19)	−0.03795 (13)	0.07449 (11)	0.0291 (4)
H23A	0.6199	−0.0649	0.1254	0.035*
C24A	0.4212 (2)	0.10468 (14)	−0.01456 (11)	0.0304 (4)
H24A	0.3668	0.1769	−0.0253	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0254 (7)	0.0382 (8)	0.0599 (9)	−0.0094 (6)	0.0024 (6)	−0.0040 (7)
C1	0.0258 (10)	0.0291 (9)	0.0391 (11)	−0.0106 (8)	0.0020 (8)	−0.0035 (8)
C2	0.0316 (11)	0.0262 (9)	0.0325 (10)	−0.0113 (8)	0.0023 (8)	−0.0081 (8)
C3	0.0400 (12)	0.0426 (11)	0.0327 (10)	−0.0229 (9)	0.0017 (9)	−0.0074 (9)
C4	0.0547 (14)	0.0472 (12)	0.0294 (10)	−0.0296 (11)	0.0074 (10)	−0.0085 (9)
C5	0.0571 (14)	0.0333 (10)	0.0276 (10)	−0.0131 (10)	0.0010 (10)	−0.0100 (8)
C6	0.0386 (12)	0.0354 (10)	0.0388 (11)	−0.0043 (9)	−0.0038 (9)	−0.0079 (9)
C7	0.0337 (11)	0.0316 (10)	0.0405 (11)	−0.0100 (9)	0.0036 (9)	−0.0035 (9)
C8	0.0844 (18)	0.0526 (13)	0.0315 (11)	−0.0156 (13)	−0.0028 (12)	−0.0033 (10)
C9	0.0327 (11)	0.0381 (11)	0.0346 (10)	−0.0207 (9)	−0.0022 (9)	0.0041 (9)
C10	0.0390 (12)	0.0402 (11)	0.0301 (10)	−0.0174 (9)	−0.0015 (9)	−0.0021 (9)
C11	0.0498 (13)	0.0502 (12)	0.0343 (11)	−0.0266 (11)	0.0017 (10)	−0.0056 (10)
C12	0.0635 (15)	0.0644 (15)	0.0319 (11)	−0.0436 (13)	−0.0034 (11)	0.0028 (10)
C13	0.0614 (16)	0.0660 (16)	0.0457 (13)	−0.0399 (13)	−0.0225 (12)	0.0165 (12)
C14	0.0472 (13)	0.0454 (12)	0.0505 (13)	−0.0261 (10)	−0.0138 (11)	0.0101 (10)
C15	0.094 (2)	0.0962 (19)	0.0373 (12)	−0.0609 (17)	−0.0117 (13)	−0.0038 (13)
C16	0.0259 (10)	0.0302 (10)	0.0371 (10)	−0.0108 (8)	−0.0012 (8)	0.0019 (8)
C17	0.0339 (11)	0.0348 (10)	0.0412 (11)	−0.0147 (9)	0.0018 (9)	−0.0043 (9)
C18	0.0338 (11)	0.0436 (11)	0.0428 (12)	−0.0152 (9)	0.0080 (9)	−0.0058 (9)
C19	0.0364 (12)	0.0387 (11)	0.0474 (12)	−0.0210 (9)	0.0045 (10)	−0.0009 (9)
C20	0.0371 (12)	0.0301 (10)	0.0457 (12)	−0.0162 (9)	0.0014 (9)	−0.0032 (9)
C21	0.0276 (10)	0.0279 (9)	0.0370 (10)	−0.0073 (8)	−0.0007 (8)	0.0001 (8)
C22	0.0299 (11)	0.0272 (9)	0.0437 (11)	−0.0136 (8)	0.0018 (9)	−0.0033 (9)
C23	0.0368 (11)	0.0284 (10)	0.0400 (11)	−0.0116 (9)	0.0013 (9)	−0.0002 (8)
C24	0.0336 (11)	0.0240 (9)	0.0452 (12)	−0.0065 (8)	0.0006 (9)	−0.0025 (9)
O1A	0.0367 (8)	0.0328 (7)	0.0396 (8)	−0.0171 (6)	0.0101 (6)	−0.0117 (6)
C1A	0.0317 (11)	0.0286 (9)	0.0336 (10)	−0.0129 (8)	0.0037 (8)	−0.0091 (8)
C2A	0.0302 (11)	0.0355 (10)	0.0323 (10)	−0.0166 (9)	0.0023 (8)	−0.0082 (8)
C3A	0.0342 (11)	0.0373 (10)	0.0394 (11)	−0.0159 (9)	0.0039 (9)	−0.0053 (9)
C4A	0.0394 (12)	0.0489 (12)	0.0329 (10)	−0.0234 (10)	0.0020 (9)	−0.0031 (9)
C5A	0.0295 (11)	0.0561 (13)	0.0357 (11)	−0.0197 (10)	0.0043 (9)	−0.0112 (10)
C6A	0.0342 (12)	0.0507 (12)	0.0395 (11)	−0.0067 (10)	0.0027 (9)	−0.0157 (10)
C7A	0.0336 (11)	0.0438 (11)	0.0328 (10)	−0.0097 (9)	0.0014 (9)	−0.0078 (9)
C8A	0.0394 (13)	0.0811 (16)	0.0383 (12)	−0.0188 (12)	0.0096 (10)	−0.0133 (11)
C9A	0.0282 (10)	0.0370 (10)	0.0269 (9)	−0.0113 (8)	0.0062 (8)	−0.0108 (8)
C10A	0.0441 (12)	0.0521 (12)	0.0314 (10)	−0.0259 (10)	0.0013 (9)	−0.0066 (9)
C11A	0.0469 (13)	0.0635 (14)	0.0324 (11)	−0.0267 (11)	−0.0034 (10)	−0.0097 (10)
C12A	0.0380 (12)	0.0450 (11)	0.0292 (10)	−0.0071 (10)	0.0028 (9)	−0.0115 (9)
C13A	0.0368 (12)	0.0318 (10)	0.0423 (11)	−0.0058 (9)	0.0025 (9)	−0.0070 (9)
C14A	0.0312 (11)	0.0312 (10)	0.0423 (11)	−0.0070 (8)	−0.0005 (9)	−0.0098 (9)
C15A	0.0564 (15)	0.0572 (13)	0.0381 (12)	−0.0108 (11)	−0.0068 (11)	−0.0107 (10)
C16A	0.0313 (11)	0.0289 (9)	0.0286 (9)	−0.0122 (8)	−0.0007 (8)	−0.0018 (8)
C17A	0.0360 (11)	0.0334 (10)	0.0349 (10)	−0.0149 (9)	0.0034 (9)	−0.0072 (8)
C18A	0.0452 (13)	0.0393 (11)	0.0363 (11)	−0.0230 (10)	0.0002 (9)	−0.0092 (9)
C19A	0.0362 (12)	0.0478 (12)	0.0476 (12)	−0.0241 (10)	−0.0009 (10)	−0.0097 (10)
C20A	0.0283 (11)	0.0411 (11)	0.0430 (11)	−0.0139 (9)	0.0036 (9)	−0.0107 (9)
C21A	0.0292 (10)	0.0268 (9)	0.0286 (9)	−0.0101 (8)	0.0002 (8)	−0.0019 (8)
C22A	0.0226 (9)	0.0289 (9)	0.0287 (9)	−0.0111 (8)	0.0051 (8)	−0.0042 (8)
C23A	0.0259 (10)	0.0332 (10)	0.0263 (9)	−0.0072 (8)	0.0000 (8)	−0.0022 (8)
C24A	0.0292 (10)	0.0259 (9)	0.0319 (10)	−0.0055 (8)	0.0044 (8)	−0.0018 (8)

Geometric parameters (Å, º)

O1—C1	1.440 (2)	O1A—C1A	1.4433 (19)
O1—H1	0.8400	O1A—H1A	0.8400
C1—C2	1.527 (2)	C1A—C9A	1.531 (2)
C1—C9	1.528 (3)	C1A—C2A	1.532 (2)
C1—C16	1.546 (2)	C1A—C16A	1.544 (2)
C2—C7	1.383 (3)	C2A—C7A	1.385 (3)
C2—C3	1.393 (2)	C2A—C3A	1.390 (2)
C3—C4	1.381 (3)	C3A—C4A	1.382 (3)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.384 (3)	C4A—C5A	1.388 (3)
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.384 (3)	C5A—C6A	1.383 (3)
C5—C8	1.501 (3)	C5A—C8A	1.510 (3)
C6—C7	1.383 (3)	C6A—C7A	1.391 (3)
C6—H6	0.9500	C6A—H6A	0.9500
C7—H7	0.9500	C7A—H7A	0.9500
C8—H8A	0.9800	C8A—H8A1	0.9800
C8—H8B	0.9800	C8A—H8A2	0.9800
C8—H8C	0.9800	C8A—H8A3	0.9800
C9—C10	1.389 (3)	C9A—C14A	1.386 (2)
C9—C14	1.391 (3)	C9A—C10A	1.387 (3)
C10—C11	1.385 (3)	C10A—C11A	1.385 (3)
C10—H10	0.9500	C10A—H10A	0.9500
C11—C12	1.388 (3)	C11A—C12A	1.382 (3)
C11—H11	0.9500	C11A—H11A	0.9500
C12—C13	1.387 (3)	C12A—C13A	1.380 (3)
C12—C15	1.500 (3)	C12A—C15A	1.503 (3)
C13—C14	1.383 (3)	C13A—C14A	1.384 (3)
C13—H13	0.9500	C13A—H13A	0.9500
C14—H14	0.9500	C14A—H14A	0.9500
C15—H15A	0.9800	C15A—H15D	0.9800
C15—H15B	0.9800	C15A—H15E	0.9800
C15—H15C	0.9800	C15A—H15F	0.9800
C16—C17	1.390 (2)	C16A—C17A	1.392 (2)
C16—C21	1.403 (2)	C16A—C21A	1.405 (2)
C17—C18	1.389 (2)	C17A—C18A	1.383 (3)
C17—H17	0.9500	C17A—H17A	0.9500
C18—C19	1.373 (3)	C18A—C19A	1.371 (3)
C18—H18	0.9500	C18A—H18A	0.9500
C19—C20	1.378 (3)	C19A—C20A	1.381 (3)
C19—H19	0.9500	C19A—H19A	0.9500
C20—C21	1.398 (2)	C20A—C21A	1.394 (2)
C20—H20	0.9500	C20A—H20A	0.9500
C21—C22	1.495 (3)	C21A—C22A	1.499 (2)
C22—C23	1.394 (2)	C22A—C23A	1.392 (2)
C22—C24^i	1.395 (3)	C22A—C24A	1.396 (2)
C23—C24	1.379 (3)	C23A—C24A^ii	1.381 (2)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C22^i	1.395 (3)	C24A—C23A^ii	1.381 (2)
C24—H24	0.9500	C24A—H24A	0.9500
C1—O1—H1	109.5	C1A—O1A—H1A	109.5
O1—C1—C2	109.86 (14)	O1A—C1A—C9A	109.37 (14)
O1—C1—C9	103.53 (14)	O1A—C1A—C2A	103.42 (13)
C2—C1—C9	110.18 (14)	C9A—C1A—C2A	111.55 (15)
O1—C1—C16	110.79 (14)	O1A—C1A—C16A	110.47 (14)
C2—C1—C16	110.98 (14)	C9A—C1A—C16A	111.16 (14)
C9—C1—C16	111.25 (14)	C2A—C1A—C16A	110.61 (14)
C7—C2—C3	117.54 (17)	C7A—C2A—C3A	118.05 (17)
C7—C2—C1	123.43 (16)	C7A—C2A—C1A	122.84 (16)
C3—C2—C1	119.01 (16)	C3A—C2A—C1A	119.02 (16)
C4—C3—C2	120.78 (18)	C4A—C3A—C2A	120.49 (18)
C4—C3—H3	119.6	C4A—C3A—H3A	119.8
C2—C3—H3	119.6	C2A—C3A—H3A	119.8
C3—C4—C5	121.67 (18)	C3A—C4A—C5A	121.90 (18)
C3—C4—H4	119.2	C3A—C4A—H4A	119.1
C5—C4—H4	119.2	C5A—C4A—H4A	119.1
C6—C5—C4	117.41 (17)	C6A—C5A—C4A	117.34 (18)
C6—C5—C8	121.6 (2)	C6A—C5A—C8A	121.58 (19)
C4—C5—C8	121.02 (19)	C4A—C5A—C8A	121.07 (19)
C7—C6—C5	121.27 (19)	C5A—C6A—C7A	121.27 (19)
C7—C6—H6	119.4	C5A—C6A—H6A	119.4
C5—C6—H6	119.4	C7A—C6A—H6A	119.4
C6—C7—C2	121.32 (18)	C2A—C7A—C6A	120.92 (18)
C6—C7—H7	119.3	C2A—C7A—H7A	119.5
C2—C7—H7	119.3	C6A—C7A—H7A	119.5
C5—C8—H8A	109.5	C5A—C8A—H8A1	109.5
C5—C8—H8B	109.5	C5A—C8A—H8A2	109.5
H8A—C8—H8B	109.5	H8A1—C8A—H8A2	109.5
C5—C8—H8C	109.5	C5A—C8A—H8A3	109.5
H8A—C8—H8C	109.5	H8A1—C8A—H8A3	109.5
H8B—C8—H8C	109.5	H8A2—C8A—H8A3	109.5
C10—C9—C14	118.20 (18)	C14A—C9A—C10A	117.61 (17)
C10—C9—C1	122.02 (16)	C14A—C9A—C1A	122.57 (16)
C14—C9—C1	119.75 (18)	C10A—C9A—C1A	119.82 (16)
C11—C10—C9	121.01 (18)	C11A—C10A—C9A	120.82 (18)
C11—C10—H10	119.5	C11A—C10A—H10A	119.6
C9—C10—H10	119.5	C9A—C10A—H10A	119.6
C10—C11—C12	121.0 (2)	C12A—C11A—C10A	121.52 (19)
C10—C11—H11	119.5	C12A—C11A—H11A	119.2
C12—C11—H11	119.5	C10A—C11A—H11A	119.2
C13—C12—C11	117.8 (2)	C13A—C12A—C11A	117.59 (18)
C13—C12—C15	120.8 (2)	C13A—C12A—C15A	121.27 (18)
C11—C12—C15	121.5 (2)	C11A—C12A—C15A	121.14 (18)
C14—C13—C12	121.7 (2)	C12A—C13A—C14A	121.31 (18)
C14—C13—H13	119.2	C12A—C13A—H13A	119.3
C12—C13—H13	119.2	C14A—C13A—H13A	119.3
C13—C14—C9	120.4 (2)	C13A—C14A—C9A	121.14 (18)
C13—C14—H14	119.8	C13A—C14A—H14A	119.4
C9—C14—H14	119.8	C9A—C14A—H14A	119.4
C12—C15—H15A	109.5	C12A—C15A—H15D	109.5
C12—C15—H15B	109.5	C12A—C15A—H15E	109.5
H15A—C15—H15B	109.5	H15D—C15A—H15E	109.5
C12—C15—H15C	109.5	C12A—C15A—H15F	109.5
H15A—C15—H15C	109.5	H15D—C15A—H15F	109.5
H15B—C15—H15C	109.5	H15E—C15A—H15F	109.5
C17—C16—C21	118.28 (16)	C17A—C16A—C21A	118.05 (16)
C17—C16—C1	119.56 (16)	C17A—C16A—C1A	119.47 (16)
C21—C16—C1	122.13 (16)	C21A—C16A—C1A	122.47 (15)
C18—C17—C16	121.75 (18)	C18A—C17A—C16A	122.04 (18)
C18—C17—H17	119.1	C18A—C17A—H17A	119.0
C16—C17—H17	119.1	C16A—C17A—H17A	119.0
C19—C18—C17	119.95 (18)	C19A—C18A—C17A	119.82 (18)
C19—C18—H18	120.0	C19A—C18A—H18A	120.1
C17—C18—H18	120.0	C17A—C18A—H18A	120.1
C18—C19—C20	119.13 (17)	C18A—C19A—C20A	119.18 (18)
C18—C19—H19	120.4	C18A—C19A—H19A	120.4
C20—C19—H19	120.4	C20A—C19A—H19A	120.4
C19—C20—C21	121.94 (18)	C19A—C20A—C21A	121.94 (18)
C19—C20—H20	119.0	C19A—C20A—H20A	119.0
C21—C20—H20	119.0	C21A—C20A—H20A	119.0
C20—C21—C16	118.92 (17)	C20A—C21A—C16A	118.81 (16)
C20—C21—C22	116.38 (16)	C20A—C21A—C22A	116.50 (16)
C16—C21—C22	124.66 (15)	C16A—C21A—C22A	124.67 (15)
C23—C22—C24^i	117.46 (17)	C23A—C22A—C24A	117.57 (16)
C23—C22—C21	118.80 (16)	C23A—C22A—C21A	120.19 (15)
C24^i—C22—C21	123.72 (16)	C24A—C22A—C21A	122.21 (15)
C24—C23—C22	121.37 (17)	C24A^ii—C23A—C22A	121.05 (16)
C24—C23—H23	119.3	C24A^ii—C23A—H23A	119.5
C22—C23—H23	119.3	C22A—C23A—H23A	119.5
C23—C24—C22^i	121.17 (17)	C23A^ii—C24A—C22A	121.38 (16)
C23—C24—H24	119.4	C23A^ii—C24A—H24A	119.3
C22^i—C24—H24	119.4	C22A—C24A—H24A	119.3
O1—C1—C2—C7	−141.41 (17)	C9A—C1A—C2A—C7A	−23.9 (2)
C9—C1—C2—C7	105.14 (19)	C16A—C1A—C2A—C7A	100.39 (19)
C16—C1—C2—C7	−18.5 (2)	O1A—C1A—C2A—C3A	42.1 (2)
O1—C1—C2—C3	40.2 (2)	C9A—C1A—C2A—C3A	159.52 (15)
C9—C1—C2—C3	−73.2 (2)	C16A—C1A—C2A—C3A	−76.20 (19)
C16—C1—C2—C3	163.09 (16)	C7A—C2A—C3A—C4A	−1.1 (3)
C7—C2—C3—C4	0.7 (3)	C1A—C2A—C3A—C4A	175.60 (16)
C1—C2—C3—C4	179.20 (16)	C2A—C3A—C4A—C5A	0.0 (3)
C2—C3—C4—C5	0.0 (3)	C3A—C4A—C5A—C6A	1.3 (3)
C3—C4—C5—C6	−0.1 (3)	C3A—C4A—C5A—C8A	−178.21 (19)
C3—C4—C5—C8	179.45 (18)	C4A—C5A—C6A—C7A	−1.4 (3)
C4—C5—C6—C7	−0.4 (3)	C8A—C5A—C6A—C7A	178.12 (19)
C8—C5—C6—C7	179.99 (18)	C3A—C2A—C7A—C6A	1.1 (3)
C5—C6—C7—C2	1.2 (3)	C1A—C2A—C7A—C6A	−175.56 (17)
C3—C2—C7—C6	−1.3 (3)	C5A—C6A—C7A—C2A	0.2 (3)
C1—C2—C7—C6	−179.69 (16)	O1A—C1A—C9A—C14A	−143.11 (16)
O1—C1—C9—C10	−148.34 (16)	C2A—C1A—C9A—C14A	103.10 (19)
C2—C1—C9—C10	−30.9 (2)	C16A—C1A—C9A—C14A	−20.9 (2)
C16—C1—C9—C10	92.62 (19)	O1A—C1A—C9A—C10A	36.7 (2)
O1—C1—C9—C14	33.6 (2)	C2A—C1A—C9A—C10A	−77.1 (2)
C2—C1—C9—C14	151.02 (16)	C16A—C1A—C9A—C10A	158.90 (16)
C16—C1—C9—C14	−85.5 (2)	C14A—C9A—C10A—C11A	0.8 (3)
C14—C9—C10—C11	0.8 (3)	C1A—C9A—C10A—C11A	−179.01 (17)
C1—C9—C10—C11	−177.35 (16)	C9A—C10A—C11A—C12A	0.2 (3)
C9—C10—C11—C12	−0.3 (3)	C10A—C11A—C12A—C13A	−0.5 (3)
C10—C11—C12—C13	−0.5 (3)	C10A—C11A—C12A—C15A	179.87 (19)
C10—C11—C12—C15	179.95 (19)	C11A—C12A—C13A—C14A	−0.2 (3)
C11—C12—C13—C14	0.8 (3)	C15A—C12A—C13A—C14A	179.47 (18)
C15—C12—C13—C14	−179.66 (19)	C12A—C13A—C14A—C9A	1.2 (3)
C12—C13—C14—C9	−0.3 (3)	C10A—C9A—C14A—C13A	−1.4 (3)
C10—C9—C14—C13	−0.5 (3)	C1A—C9A—C14A—C13A	178.34 (17)
C1—C9—C14—C13	177.67 (17)	O1A—C1A—C16A—C17A	−138.92 (15)
O1—C1—C16—C17	−137.76 (17)	C9A—C1A—C16A—C17A	99.48 (18)
C2—C1—C16—C17	99.90 (19)	C2A—C1A—C16A—C17A	−25.0 (2)
C9—C1—C16—C17	−23.2 (2)	O1A—C1A—C16A—C21A	41.5 (2)
O1—C1—C16—C21	44.3 (2)	C9A—C1A—C16A—C21A	−80.1 (2)
C2—C1—C16—C21	−78.0 (2)	C2A—C1A—C16A—C21A	155.43 (15)
C9—C1—C16—C21	158.89 (16)	C21A—C16A—C17A—C18A	−2.1 (3)
C21—C16—C17—C18	1.2 (3)	C1A—C16A—C17A—C18A	178.37 (16)
C1—C16—C17—C18	−176.85 (17)	C16A—C17A—C18A—C19A	−1.4 (3)
C16—C17—C18—C19	−1.0 (3)	C17A—C18A—C19A—C20A	2.4 (3)
C17—C18—C19—C20	−0.5 (3)	C18A—C19A—C20A—C21A	0.1 (3)
C18—C19—C20—C21	1.8 (3)	C19A—C20A—C21A—C16A	−3.5 (3)
C19—C20—C21—C16	−1.5 (3)	C19A—C20A—C21A—C22A	177.61 (16)
C19—C20—C21—C22	−179.29 (17)	C17A—C16A—C21A—C20A	4.4 (2)
C17—C16—C21—C20	0.1 (3)	C1A—C16A—C21A—C20A	−176.03 (16)
C1—C16—C21—C20	178.03 (16)	C17A—C16A—C21A—C22A	−176.83 (15)
C17—C16—C21—C22	177.62 (16)	C1A—C16A—C21A—C22A	2.7 (3)
C1—C16—C21—C22	−4.4 (3)	C20A—C21A—C22A—C23A	65.4 (2)
C20—C21—C22—C23	66.0 (2)	C16A—C21A—C22A—C23A	−113.38 (19)
C16—C21—C22—C23	−111.6 (2)	C20A—C21A—C22A—C24A	−112.39 (19)
C20—C21—C22—C24^i	−112.7 (2)	C16A—C21A—C22A—C24A	68.8 (2)
C16—C21—C22—C24^i	69.7 (3)	C24A—C22A—C23A—C24A^ii	−0.4 (3)
C24^i—C22—C23—C24	−0.4 (3)	C21A—C22A—C23A—C24A^ii	−178.33 (16)
C21—C22—C23—C24	−179.17 (17)	C23A—C22A—C24A—C23A^ii	0.4 (3)
C22—C23—C24—C22^i	0.4 (3)	C21A—C22A—C24A—C23A^ii	178.29 (16)
O1A—C1A—C2A—C7A	−141.33 (17)

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

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of which? ring. [Symmetry code: (A) Please complete]

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cg4	0.84	2.63	3.443 (3)	166
O1A—H1A···Cg4A	0.84	2.67	3.494 (3)	167
C8A—H8A1···O1^iii	0.98	2.58	3.451 (2)	148
C19—H19···O1A^iv	0.95	2.46	3.393 (2)	167

Symmetry codes: (iii) −x, −y+1, −z+1; (iv) x+1, y+1, z.

(IIIA) 2,2''-Bis[hydroxybis(4-methylphenyl)methyl]-1,1':4',1''-terphenyl dimethylformamide monosolvate

Crystal data

C48H42O2·C3H7NO	Z = 2
Mr = 723.91	F(000) = 772
Triclinic, P1	Dx = 1.228 Mg m^−3
a = 8.9604 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8542 (4) Å	Cell parameters from 9636 reflections
c = 22.0219 (8) Å	θ = 2.5–29.3°
α = 92.689 (2)°	µ = 0.08 mm^−1
β = 93.978 (2)°	T = 100 K
γ = 113.200 (2)°	Irregular, colourless
V = 1957.42 (12) Å^3	0.42 × 0.41 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	Rint = 0.029
φ and ω scans	θmax = 29.1°, θmin = 0.9°
38812 measured reflections	h = −12→12
10443 independent reflections	k = −14→13
7755 reflections with I > 2σ(I)	l = −29→30

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0679P)^2 + 0.6977P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
10443 reflections	Δρmax = 0.41 e Å^−3
501 parameters	Δρmin = −0.33 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.13759 (10)	1.09087 (9)	0.21454 (4)	0.01584 (18)
H1	1.1138	1.1574	0.2214	0.024*
O2	0.35174 (10)	0.40772 (9)	0.29017 (4)	0.01625 (18)
H2	0.2502	0.3826	0.2838	0.024*
C1	1.08324 (13)	1.03688 (12)	0.15255 (5)	0.0128 (2)
C2	1.08372 (14)	0.89613 (12)	0.14676 (5)	0.0148 (2)
C3	0.98672 (15)	0.79998 (13)	0.10082 (6)	0.0196 (3)
H3	0.9088	0.8178	0.0753	0.024*
C4	1.00213 (16)	0.67784 (14)	0.09168 (7)	0.0245 (3)
H4	0.9352	0.6141	0.0597	0.029*
C5	1.11340 (17)	0.64734 (14)	0.12840 (7)	0.0255 (3)
C6	1.20681 (16)	0.74226 (14)	0.17550 (7)	0.0243 (3)
H6	1.2813	0.7227	0.2021	0.029*
C7	1.19338 (14)	0.86514 (13)	0.18450 (6)	0.0193 (3)
H7	1.2596	0.9285	0.2167	0.023*
C8	1.1335 (2)	0.51650 (16)	0.11763 (9)	0.0374 (4)
H8A	1.0536	0.4604	0.0844	0.056*
H8B	1.1161	0.4691	0.1550	0.056*
H8C	1.2439	0.5352	0.1065	0.056*
C9	1.20818 (13)	1.12468 (12)	0.11079 (5)	0.0132 (2)
C10	1.20997 (14)	1.07949 (13)	0.05047 (5)	0.0165 (2)
H10	1.1319	0.9937	0.0345	0.020*
C11	1.32410 (15)	1.15808 (13)	0.01353 (6)	0.0180 (2)
H11	1.3224	1.1252	−0.0274	0.022*
C12	1.44068 (14)	1.28382 (13)	0.03521 (6)	0.0181 (2)
C13	1.43746 (15)	1.33020 (13)	0.09486 (6)	0.0184 (2)
H13	1.5145	1.4167	0.1104	0.022*
C14	1.32307 (14)	1.25192 (12)	0.13230 (5)	0.0163 (2)
H14	1.3235	1.2858	0.1729	0.020*
C15	1.56745 (17)	1.36540 (15)	−0.00511 (6)	0.0258 (3)
H15A	1.6462	1.4463	0.0186	0.039*
H15B	1.5140	1.3914	−0.0395	0.039*
H15C	1.6243	1.3113	−0.0206	0.039*
C16	0.91220 (13)	1.03572 (12)	0.13667 (5)	0.0129 (2)
C17	0.89481 (14)	1.12670 (12)	0.09691 (5)	0.0165 (2)
H17	0.9883	1.1853	0.0794	0.020*
C18	0.74576 (15)	1.13483 (13)	0.08193 (6)	0.0195 (3)
H18	0.7384	1.1983	0.0549	0.023*
C19	0.60825 (15)	1.04962 (14)	0.10681 (6)	0.0198 (3)
H19	0.5053	1.0533	0.0967	0.024*
C20	0.62291 (14)	0.95906 (13)	0.14657 (6)	0.0179 (2)
H20	0.5281	0.9008	0.1634	0.022*
C21	0.77217 (14)	0.94962 (12)	0.16300 (5)	0.0140 (2)
C22	0.76298 (14)	0.84591 (12)	0.20682 (5)	0.0148 (2)
C23	0.85706 (15)	0.87373 (13)	0.26301 (6)	0.0193 (3)
H23	0.9389	0.9613	0.2736	0.023*
C24	0.83251 (15)	0.77517 (13)	0.30357 (6)	0.0193 (3)
H24	0.8991	0.7968	0.3412	0.023*
C25	0.71307 (14)	0.64529 (13)	0.29079 (5)	0.0151 (2)
C26	0.61744 (14)	0.61762 (13)	0.23499 (6)	0.0179 (2)
H26	0.5342	0.5305	0.2248	0.022*
C27	0.64273 (14)	0.71627 (13)	0.19420 (6)	0.0175 (2)
H27	0.5760	0.6947	0.1565	0.021*
C28	0.70786 (14)	0.54095 (12)	0.33381 (5)	0.0143 (2)
C29	0.85610 (14)	0.52683 (13)	0.34518 (6)	0.0181 (2)
H29	0.9473	0.5814	0.3253	0.022*
C30	0.87480 (15)	0.43633 (14)	0.38428 (6)	0.0198 (3)
H30	0.9764	0.4282	0.3905	0.024*
C31	0.74297 (15)	0.35799 (13)	0.41406 (6)	0.0198 (3)
H31	0.7536	0.2959	0.4413	0.024*
C32	0.59477 (15)	0.37075 (13)	0.40392 (5)	0.0172 (2)
H32	0.5053	0.3171	0.4248	0.021*
C33	0.57349 (13)	0.45985 (12)	0.36399 (5)	0.0135 (2)
C34	0.40355 (13)	0.46278 (12)	0.35202 (5)	0.0127 (2)
C35	0.41037 (14)	0.60586 (12)	0.36066 (5)	0.0150 (2)
C36	0.51924 (15)	0.70029 (13)	0.40494 (6)	0.0212 (3)
H36	0.5968	0.6782	0.4285	0.025*
C37	0.51588 (17)	0.82648 (14)	0.41506 (7)	0.0279 (3)
H37	0.5913	0.8892	0.4455	0.033*
C38	0.40456 (17)	0.86288 (14)	0.38159 (7)	0.0277 (3)
C39	0.29643 (17)	0.76851 (14)	0.33749 (7)	0.0257 (3)
H39	0.2192	0.7909	0.3139	0.031*
C40	0.29873 (15)	0.64192 (13)	0.32716 (6)	0.0202 (3)
H40	0.2229	0.5792	0.2968	0.024*
C41	0.4027 (2)	1.00070 (16)	0.39214 (9)	0.0411 (4)
H41A	0.4756	1.0621	0.3656	0.062*
H41B	0.4398	1.0345	0.4349	0.062*
H41C	0.2915	0.9950	0.3828	0.062*
C42	0.28119 (13)	0.37414 (12)	0.39407 (5)	0.0139 (2)
C43	0.26677 (15)	0.42363 (13)	0.45210 (5)	0.0175 (2)
H43	0.3363	0.5131	0.4668	0.021*
C44	0.15206 (15)	0.34380 (14)	0.48865 (6)	0.0196 (3)
H44	0.1458	0.3793	0.5282	0.024*
C45	0.04658 (15)	0.21329 (14)	0.46849 (6)	0.0198 (3)
C46	0.06272 (16)	0.16258 (13)	0.41125 (6)	0.0213 (3)
H46	−0.0066	0.0729	0.3968	0.026*
C47	0.17918 (15)	0.24149 (13)	0.37475 (6)	0.0179 (2)
H47	0.1891	0.2042	0.3361	0.021*
C48	−0.08221 (17)	0.13046 (16)	0.50776 (7)	0.0290 (3)
H48A	−0.1657	0.1673	0.5098	0.044*
H48B	−0.0317	0.1331	0.5490	0.044*
H48C	−0.1328	0.0372	0.4900	0.044*
O1A	1.0321 (2)	0.3066 (2)	0.24051 (9)	0.0190 (5)*	0.709 (2)
N1A	0.76408 (18)	0.27208 (17)	0.23653 (8)	0.0187 (3)*	0.709 (2)
C1A	0.8882 (2)	0.2419 (2)	0.25474 (9)	0.0193 (4)*	0.709 (2)
H1A	0.8693	0.1688	0.2795	0.023*	0.709 (2)
C2A	0.6000 (2)	0.1940 (2)	0.25318 (10)	0.0245 (4)*	0.709 (2)
H2A1	0.6012	0.1193	0.2762	0.037*	0.709 (2)
H2A2	0.5248	0.1585	0.2161	0.037*	0.709 (2)
H2A3	0.5641	0.2520	0.2784	0.037*	0.709 (2)
C3A	0.7877 (2)	0.3836 (2)	0.19952 (9)	0.0237 (4)*	0.709 (2)
H3A1	0.9001	0.4504	0.2078	0.035*	0.709 (2)
H3A2	0.7121	0.4251	0.2094	0.035*	0.709 (2)
H3A3	0.7668	0.3511	0.1562	0.035*	0.709 (2)
O1AA	1.0227 (5)	0.2869 (5)	0.2486 (2)	0.0196 (12)*	0.291 (2)
N1AA	0.7547 (4)	0.2232 (4)	0.25552 (19)	0.0204 (9)*	0.291 (2)
C2AA	0.7509 (6)	0.1213 (5)	0.2976 (2)	0.0297 (12)*	0.291 (2)
H2A4	0.8564	0.1135	0.3005	0.045*	0.291 (2)
H2A5	0.6646	0.0344	0.2822	0.045*	0.291 (2)
H2A6	0.7291	0.1479	0.3380	0.045*	0.291 (2)
C1AA	0.8921 (5)	0.2997 (5)	0.2356 (2)	0.0235 (10)*	0.291 (2)
H1AA	0.8927	0.3681	0.2102	0.028*	0.291 (2)
C3AA	0.6016 (6)	0.2358 (6)	0.2407 (2)	0.0245 (4)*	0.291 (2)
H3A4	0.6186	0.3082	0.2135	0.037*	0.291 (2)
H3A5	0.5609	0.2570	0.2782	0.037*	0.291 (2)
H3A6	0.5217	0.1510	0.2202	0.037*	0.291 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0168 (4)	0.0165 (4)	0.0130 (4)	0.0059 (3)	−0.0006 (3)	0.0005 (3)
O2	0.0136 (4)	0.0200 (5)	0.0127 (4)	0.0045 (3)	−0.0004 (3)	−0.0003 (3)
C1	0.0118 (5)	0.0128 (6)	0.0130 (5)	0.0043 (4)	−0.0001 (4)	0.0012 (4)
C2	0.0129 (5)	0.0143 (6)	0.0183 (6)	0.0059 (4)	0.0042 (4)	0.0036 (4)
C3	0.0169 (5)	0.0171 (6)	0.0245 (6)	0.0067 (5)	0.0015 (5)	−0.0002 (5)
C4	0.0235 (6)	0.0157 (7)	0.0323 (7)	0.0054 (5)	0.0069 (5)	−0.0014 (5)
C5	0.0254 (6)	0.0169 (7)	0.0394 (8)	0.0106 (5)	0.0173 (6)	0.0106 (6)
C6	0.0207 (6)	0.0249 (7)	0.0344 (7)	0.0141 (5)	0.0097 (5)	0.0148 (6)
C7	0.0152 (5)	0.0199 (6)	0.0234 (6)	0.0069 (5)	0.0029 (4)	0.0076 (5)
C8	0.0450 (9)	0.0233 (8)	0.0553 (10)	0.0213 (7)	0.0254 (8)	0.0140 (7)
C9	0.0120 (5)	0.0147 (6)	0.0141 (5)	0.0064 (4)	0.0007 (4)	0.0029 (4)
C10	0.0158 (5)	0.0168 (6)	0.0160 (6)	0.0059 (5)	0.0001 (4)	0.0000 (4)
C11	0.0201 (6)	0.0224 (7)	0.0136 (5)	0.0104 (5)	0.0018 (4)	0.0026 (5)
C12	0.0170 (5)	0.0212 (6)	0.0181 (6)	0.0090 (5)	0.0030 (4)	0.0075 (5)
C13	0.0174 (5)	0.0145 (6)	0.0199 (6)	0.0028 (5)	0.0013 (4)	0.0029 (5)
C14	0.0171 (5)	0.0155 (6)	0.0151 (5)	0.0053 (5)	0.0015 (4)	0.0012 (4)
C15	0.0253 (6)	0.0271 (8)	0.0251 (7)	0.0084 (6)	0.0100 (5)	0.0102 (6)
C16	0.0122 (5)	0.0139 (6)	0.0128 (5)	0.0057 (4)	0.0006 (4)	−0.0009 (4)
C17	0.0166 (5)	0.0159 (6)	0.0177 (6)	0.0073 (5)	0.0018 (4)	0.0020 (5)
C18	0.0210 (6)	0.0193 (7)	0.0213 (6)	0.0115 (5)	0.0002 (5)	0.0040 (5)
C19	0.0167 (5)	0.0246 (7)	0.0214 (6)	0.0123 (5)	−0.0005 (4)	0.0005 (5)
C20	0.0143 (5)	0.0215 (7)	0.0189 (6)	0.0079 (5)	0.0030 (4)	0.0011 (5)
C21	0.0145 (5)	0.0153 (6)	0.0120 (5)	0.0059 (4)	0.0011 (4)	0.0003 (4)
C22	0.0135 (5)	0.0180 (6)	0.0137 (5)	0.0064 (4)	0.0036 (4)	0.0032 (4)
C23	0.0178 (5)	0.0181 (6)	0.0164 (6)	0.0013 (5)	−0.0004 (4)	0.0027 (5)
C24	0.0169 (5)	0.0223 (7)	0.0148 (6)	0.0037 (5)	−0.0015 (4)	0.0035 (5)
C25	0.0131 (5)	0.0184 (6)	0.0143 (5)	0.0062 (4)	0.0031 (4)	0.0026 (4)
C26	0.0161 (5)	0.0172 (6)	0.0168 (6)	0.0028 (5)	0.0000 (4)	0.0017 (5)
C27	0.0155 (5)	0.0199 (6)	0.0146 (5)	0.0047 (5)	−0.0011 (4)	0.0022 (5)
C28	0.0146 (5)	0.0156 (6)	0.0127 (5)	0.0061 (4)	0.0007 (4)	0.0005 (4)
C29	0.0144 (5)	0.0228 (7)	0.0180 (6)	0.0083 (5)	0.0025 (4)	0.0008 (5)
C30	0.0179 (6)	0.0245 (7)	0.0209 (6)	0.0130 (5)	−0.0007 (5)	−0.0004 (5)
C31	0.0222 (6)	0.0199 (7)	0.0209 (6)	0.0125 (5)	−0.0007 (5)	0.0033 (5)
C32	0.0182 (5)	0.0174 (6)	0.0168 (6)	0.0078 (5)	0.0019 (4)	0.0029 (5)
C33	0.0134 (5)	0.0142 (6)	0.0136 (5)	0.0067 (4)	0.0003 (4)	−0.0005 (4)
C34	0.0122 (5)	0.0134 (6)	0.0120 (5)	0.0046 (4)	0.0001 (4)	0.0007 (4)
C35	0.0138 (5)	0.0138 (6)	0.0185 (6)	0.0059 (4)	0.0050 (4)	0.0033 (4)
C36	0.0173 (6)	0.0174 (6)	0.0276 (7)	0.0062 (5)	0.0011 (5)	−0.0023 (5)
C37	0.0228 (6)	0.0165 (7)	0.0401 (8)	0.0035 (5)	0.0071 (6)	−0.0067 (6)
C38	0.0276 (7)	0.0160 (7)	0.0442 (9)	0.0101 (5)	0.0209 (6)	0.0088 (6)
C39	0.0267 (7)	0.0248 (7)	0.0343 (8)	0.0170 (6)	0.0119 (6)	0.0132 (6)
C40	0.0187 (6)	0.0208 (7)	0.0239 (6)	0.0100 (5)	0.0039 (5)	0.0069 (5)
C41	0.0494 (10)	0.0190 (8)	0.0638 (12)	0.0178 (7)	0.0326 (9)	0.0107 (7)
C42	0.0127 (5)	0.0150 (6)	0.0146 (5)	0.0060 (4)	0.0008 (4)	0.0031 (4)
C43	0.0182 (5)	0.0179 (6)	0.0153 (6)	0.0061 (5)	0.0010 (4)	0.0004 (5)
C44	0.0217 (6)	0.0246 (7)	0.0150 (6)	0.0112 (5)	0.0042 (4)	0.0036 (5)
C45	0.0176 (5)	0.0234 (7)	0.0199 (6)	0.0084 (5)	0.0039 (4)	0.0101 (5)
C46	0.0223 (6)	0.0158 (6)	0.0215 (6)	0.0029 (5)	0.0019 (5)	0.0044 (5)
C47	0.0213 (6)	0.0150 (6)	0.0159 (6)	0.0057 (5)	0.0023 (4)	0.0022 (5)
C48	0.0259 (7)	0.0324 (8)	0.0271 (7)	0.0075 (6)	0.0097 (5)	0.0138 (6)

Geometric parameters (Å, º)

O1—C1	1.4324 (13)	C29—H29	0.9500
O1—H1	0.8400	C30—C31	1.3846 (18)
O2—C34	1.4300 (13)	C30—H30	0.9500
O2—H2	0.8400	C31—C32	1.3925 (16)
C1—C2	1.5288 (17)	C31—H31	0.9500
C1—C16	1.5432 (15)	C32—C33	1.3951 (17)
C1—C9	1.5466 (16)	C32—H32	0.9500
C2—C3	1.3900 (17)	C33—C34	1.5403 (15)
C2—C7	1.3938 (16)	C34—C35	1.5323 (17)
C3—C4	1.3928 (18)	C34—C42	1.5423 (16)
C3—H3	0.9500	C35—C40	1.3897 (17)
C4—C5	1.389 (2)	C35—C36	1.3927 (17)
C4—H4	0.9500	C36—C37	1.3897 (19)
C5—C6	1.392 (2)	C36—H36	0.9500
C5—C8	1.511 (2)	C37—C38	1.389 (2)
C6—C7	1.3920 (19)	C37—H37	0.9500
C6—H6	0.9500	C38—C39	1.388 (2)
C7—H7	0.9500	C38—C41	1.510 (2)
C8—H8A	0.9800	C39—C40	1.3907 (19)
C8—H8B	0.9800	C39—H39	0.9500
C8—H8C	0.9800	C40—H40	0.9500
C9—C14	1.3937 (17)	C41—H41A	0.9800
C9—C10	1.3976 (16)	C41—H41B	0.9800
C10—C11	1.3887 (17)	C41—H41C	0.9800
C10—H10	0.9500	C42—C47	1.3933 (17)
C11—C12	1.3886 (18)	C42—C43	1.3968 (16)
C11—H11	0.9500	C43—C44	1.3906 (17)
C12—C13	1.3909 (18)	C43—H43	0.9500
C12—C15	1.5112 (17)	C44—C45	1.3875 (19)
C13—C14	1.3960 (16)	C44—H44	0.9500
C13—H13	0.9500	C45—C46	1.3913 (18)
C14—H14	0.9500	C45—C48	1.5106 (17)
C15—H15A	0.9800	C46—C47	1.3947 (17)
C15—H15B	0.9800	C46—H46	0.9500
C15—H15C	0.9800	C47—H47	0.9500
C16—C17	1.3963 (17)	C48—H48A	0.9800
C16—C21	1.4184 (16)	C48—H48B	0.9800
C17—C18	1.3909 (16)	C48—H48C	0.9800
C17—H17	0.9500	O1A—C1A	1.272 (3)
C18—C19	1.3847 (18)	N1A—C1A	1.320 (2)
C18—H18	0.9500	N1A—C3A	1.446 (3)
C19—C20	1.3844 (18)	N1A—C2A	1.461 (3)
C19—H19	0.9500	C1A—H1A	0.9500
C20—C21	1.4051 (16)	C2A—H2A1	0.9800
C20—H20	0.9500	C2A—H2A2	0.9800
C21—C22	1.4985 (16)	C2A—H2A3	0.9800
C22—C27	1.3947 (17)	C3A—H3A1	0.9800
C22—C23	1.3973 (16)	C3A—H3A2	0.9800
C23—C24	1.3864 (17)	C3A—H3A3	0.9800
C23—H23	0.9500	O1AA—C1AA	1.247 (6)
C24—C25	1.3943 (17)	N1AA—C1AA	1.304 (6)
C24—H24	0.9500	N1AA—C3AA	1.449 (6)
C25—C26	1.3968 (16)	N1AA—C2AA	1.467 (7)
C25—C28	1.4991 (17)	C2AA—H2A4	0.9800
C26—C27	1.3900 (17)	C2AA—H2A5	0.9800
C26—H26	0.9500	C2AA—H2A6	0.9800
C27—H27	0.9500	C1AA—H1AA	0.9500
C28—C29	1.4030 (16)	C3AA—H3A4	0.9800
C28—C33	1.4132 (16)	C3AA—H3A5	0.9800
C29—C30	1.3870 (18)	C3AA—H3A6	0.9800
C1—O1—H1	109.5	C29—C30—H30	120.5
C34—O2—H2	109.5	C30—C31—C32	119.62 (12)
O1—C1—C2	107.82 (9)	C30—C31—H31	120.2
O1—C1—C16	108.67 (9)	C32—C31—H31	120.2
C2—C1—C16	112.52 (9)	C31—C32—C33	122.08 (11)
O1—C1—C9	108.52 (9)	C31—C32—H32	119.0
C2—C1—C9	107.52 (9)	C33—C32—H32	119.0
C16—C1—C9	111.65 (9)	C32—C33—C28	118.63 (10)
C3—C2—C7	118.05 (12)	C32—C33—C34	119.32 (10)
C3—C2—C1	121.56 (10)	C28—C33—C34	122.00 (10)
C7—C2—C1	120.14 (11)	O2—C34—C35	111.43 (9)
C2—C3—C4	120.92 (12)	O2—C34—C33	104.10 (9)
C2—C3—H3	119.5	C35—C34—C33	111.82 (9)
C4—C3—H3	119.5	O2—C34—C42	109.07 (9)
C5—C4—C3	121.31 (13)	C35—C34—C42	108.23 (9)
C5—C4—H4	119.3	C33—C34—C42	112.15 (9)
C3—C4—H4	119.3	C40—C35—C36	117.90 (12)
C4—C5—C6	117.56 (12)	C40—C35—C34	120.33 (11)
C4—C5—C8	121.48 (14)	C36—C35—C34	121.60 (11)
C6—C5—C8	120.96 (14)	C37—C36—C35	120.80 (12)
C7—C6—C5	121.44 (12)	C37—C36—H36	119.6
C7—C6—H6	119.3	C35—C36—H36	119.6
C5—C6—H6	119.3	C38—C37—C36	121.44 (13)
C6—C7—C2	120.67 (12)	C38—C37—H37	119.3
C6—C7—H7	119.7	C36—C37—H37	119.3
C2—C7—H7	119.7	C39—C38—C37	117.55 (13)
C5—C8—H8A	109.5	C39—C38—C41	121.14 (15)
C5—C8—H8B	109.5	C37—C38—C41	121.29 (15)
H8A—C8—H8B	109.5	C38—C39—C40	121.38 (13)
C5—C8—H8C	109.5	C38—C39—H39	119.3
H8A—C8—H8C	109.5	C40—C39—H39	119.3
H8B—C8—H8C	109.5	C35—C40—C39	120.93 (13)
C14—C9—C10	117.81 (11)	C35—C40—H40	119.5
C14—C9—C1	120.84 (10)	C39—C40—H40	119.5
C10—C9—C1	121.36 (10)	C38—C41—H41A	109.5
C11—C10—C9	121.02 (11)	C38—C41—H41B	109.5
C11—C10—H10	119.5	H41A—C41—H41B	109.5
C9—C10—H10	119.5	C38—C41—H41C	109.5
C12—C11—C10	121.28 (11)	H41A—C41—H41C	109.5
C12—C11—H11	119.4	H41B—C41—H41C	109.5
C10—C11—H11	119.4	C47—C42—C43	117.70 (11)
C11—C12—C13	117.87 (11)	C47—C42—C34	120.63 (10)
C11—C12—C15	120.33 (12)	C43—C42—C34	121.67 (11)
C13—C12—C15	121.79 (12)	C44—C43—C42	120.96 (12)
C12—C13—C14	121.22 (12)	C44—C43—H43	119.5
C12—C13—H13	119.4	C42—C43—H43	119.5
C14—C13—H13	119.4	C45—C44—C43	121.28 (12)
C9—C14—C13	120.78 (11)	C45—C44—H44	119.4
C9—C14—H14	119.6	C43—C44—H44	119.4
C13—C14—H14	119.6	C44—C45—C46	117.96 (11)
C12—C15—H15A	109.5	C44—C45—C48	120.43 (12)
C12—C15—H15B	109.5	C46—C45—C48	121.61 (12)
H15A—C15—H15B	109.5	C45—C46—C47	120.99 (12)
C12—C15—H15C	109.5	C45—C46—H46	119.5
H15A—C15—H15C	109.5	C47—C46—H46	119.5
H15B—C15—H15C	109.5	C42—C47—C46	121.05 (12)
C17—C16—C21	118.32 (10)	C42—C47—H47	119.5
C17—C16—C1	119.07 (10)	C46—C47—H47	119.5
C21—C16—C1	122.55 (10)	C45—C48—H48A	109.5
C18—C17—C16	122.49 (11)	C45—C48—H48B	109.5
C18—C17—H17	118.8	H48A—C48—H48B	109.5
C16—C17—H17	118.8	C45—C48—H48C	109.5
C19—C18—C17	119.39 (12)	H48A—C48—H48C	109.5
C19—C18—H18	120.3	H48B—C48—H48C	109.5
C17—C18—H18	120.3	C1A—N1A—C3A	120.55 (17)
C20—C19—C18	119.06 (11)	C1A—N1A—C2A	121.0 (2)
C20—C19—H19	120.5	C3A—N1A—C2A	118.41 (17)
C18—C19—H19	120.5	O1A—C1A—N1A	122.7 (2)
C19—C20—C21	122.76 (11)	O1A—C1A—H1A	118.6
C19—C20—H20	118.6	N1A—C1A—H1A	118.6
C21—C20—H20	118.6	N1A—C2A—H2A1	109.5
C20—C21—C16	117.96 (11)	N1A—C2A—H2A2	109.5
C20—C21—C22	114.72 (10)	H2A1—C2A—H2A2	109.5
C16—C21—C22	127.31 (10)	N1A—C2A—H2A3	109.5
C27—C22—C23	117.09 (11)	H2A1—C2A—H2A3	109.5
C27—C22—C21	118.61 (10)	H2A2—C2A—H2A3	109.5
C23—C22—C21	123.99 (11)	N1A—C3A—H3A1	109.5
C24—C23—C22	120.87 (12)	N1A—C3A—H3A2	109.5
C24—C23—H23	119.6	H3A1—C3A—H3A2	109.5
C22—C23—H23	119.6	N1A—C3A—H3A3	109.5
C23—C24—C25	122.06 (11)	H3A1—C3A—H3A3	109.5
C23—C24—H24	119.0	H3A2—C3A—H3A3	109.5
C25—C24—H24	119.0	C1AA—N1AA—C3AA	123.7 (5)
C24—C25—C26	117.21 (11)	C1AA—N1AA—C2AA	120.0 (4)
C24—C25—C28	118.38 (10)	C3AA—N1AA—C2AA	116.2 (4)
C26—C25—C28	124.02 (11)	N1AA—C2AA—H2A4	109.5
C27—C26—C25	120.70 (12)	N1AA—C2AA—H2A5	109.5
C27—C26—H26	119.7	H2A4—C2AA—H2A5	109.5
C25—C26—H26	119.7	N1AA—C2AA—H2A6	109.5
C26—C27—C22	122.07 (11)	H2A4—C2AA—H2A6	109.5
C26—C27—H27	119.0	H2A5—C2AA—H2A6	109.5
C22—C27—H27	119.0	O1AA—C1AA—N1AA	122.8 (5)
C29—C28—C33	118.14 (11)	O1AA—C1AA—H1AA	118.6
C29—C28—C25	114.50 (10)	N1AA—C1AA—H1AA	118.6
C33—C28—C25	127.35 (10)	N1AA—C3AA—H3A4	109.5
C30—C29—C28	122.60 (11)	N1AA—C3AA—H3A5	109.5
C30—C29—H29	118.7	H3A4—C3AA—H3A5	109.5
C28—C29—H29	118.7	N1AA—C3AA—H3A6	109.5
C31—C30—C29	118.92 (11)	H3A4—C3AA—H3A6	109.5
C31—C30—H30	120.5	H3A5—C3AA—H3A6	109.5
O1—C1—C2—C3	156.82 (11)	C25—C26—C27—C22	−0.06 (19)
C16—C1—C2—C3	37.01 (15)	C23—C22—C27—C26	−0.72 (18)
C9—C1—C2—C3	−86.35 (13)	C21—C22—C27—C26	−174.51 (11)
O1—C1—C2—C7	−28.98 (14)	C24—C25—C28—C29	−53.60 (15)
C16—C1—C2—C7	−148.80 (11)	C26—C25—C28—C29	119.01 (13)
C9—C1—C2—C7	87.85 (12)	C24—C25—C28—C33	125.11 (13)
C7—C2—C3—C4	−1.84 (18)	C26—C25—C28—C33	−62.28 (18)
C1—C2—C3—C4	172.47 (11)	C33—C28—C29—C30	0.44 (18)
C2—C3—C4—C5	0.7 (2)	C25—C28—C29—C30	179.27 (12)
C3—C4—C5—C6	1.3 (2)	C28—C29—C30—C31	−0.96 (19)
C3—C4—C5—C8	−178.42 (13)	C29—C30—C31—C32	0.47 (19)
C4—C5—C6—C7	−1.98 (19)	C30—C31—C32—C33	0.53 (19)
C8—C5—C6—C7	177.70 (12)	C31—C32—C33—C28	−1.04 (18)
C5—C6—C7—C2	0.80 (19)	C31—C32—C33—C34	176.39 (11)
C3—C2—C7—C6	1.13 (18)	C29—C28—C33—C32	0.55 (17)
C1—C2—C7—C6	−173.26 (11)	C25—C28—C33—C32	−178.12 (11)
O1—C1—C9—C14	−15.69 (14)	C29—C28—C33—C34	−176.81 (10)
C2—C1—C9—C14	−132.06 (11)	C25—C28—C33—C34	4.52 (19)
C16—C1—C9—C14	104.05 (12)	C32—C33—C34—O2	−110.57 (12)
O1—C1—C9—C10	164.26 (10)	C28—C33—C34—O2	66.77 (13)
C2—C1—C9—C10	47.89 (14)	C32—C33—C34—C35	129.00 (11)
C16—C1—C9—C10	−75.99 (13)	C28—C33—C34—C35	−53.66 (14)
C14—C9—C10—C11	0.93 (17)	C32—C33—C34—C42	7.21 (15)
C1—C9—C10—C11	−179.03 (11)	C28—C33—C34—C42	−175.45 (10)
C9—C10—C11—C12	0.29 (18)	O2—C34—C35—C40	33.96 (14)
C10—C11—C12—C13	−1.42 (18)	C33—C34—C35—C40	150.01 (11)
C10—C11—C12—C15	177.79 (12)	C42—C34—C35—C40	−85.97 (13)
C11—C12—C13—C14	1.35 (18)	O2—C34—C35—C36	−150.83 (11)
C15—C12—C13—C14	−177.84 (12)	C33—C34—C35—C36	−34.78 (15)
C10—C9—C14—C13	−1.00 (17)	C42—C34—C35—C36	89.24 (13)
C1—C9—C14—C13	178.96 (11)	C40—C35—C36—C37	−0.06 (19)
C12—C13—C14—C9	−0.15 (19)	C34—C35—C36—C37	−175.39 (12)
O1—C1—C16—C17	108.66 (12)	C35—C36—C37—C38	0.0 (2)
C2—C1—C16—C17	−132.02 (11)	C36—C37—C38—C39	0.0 (2)
C9—C1—C16—C17	−11.00 (15)	C36—C37—C38—C41	−179.18 (13)
O1—C1—C16—C21	−68.50 (14)	C37—C38—C39—C40	0.2 (2)
C2—C1—C16—C21	50.83 (14)	C41—C38—C39—C40	179.33 (13)
C9—C1—C16—C21	171.84 (10)	C36—C35—C40—C39	0.20 (18)
C21—C16—C17—C18	−0.61 (18)	C34—C35—C40—C39	175.59 (11)
C1—C16—C17—C18	−177.88 (11)	C38—C39—C40—C35	−0.3 (2)
C16—C17—C18—C19	−0.33 (19)	O2—C34—C42—C47	20.93 (14)
C17—C18—C19—C20	0.61 (19)	C35—C34—C42—C47	142.32 (11)
C18—C19—C20—C21	0.1 (2)	C33—C34—C42—C47	−93.85 (13)
C19—C20—C21—C16	−0.99 (18)	O2—C34—C42—C43	−158.19 (10)
C19—C20—C21—C22	179.70 (12)	C35—C34—C42—C43	−36.79 (14)
C17—C16—C21—C20	1.23 (17)	C33—C34—C42—C43	87.03 (13)
C1—C16—C21—C20	178.40 (10)	C47—C42—C43—C44	−1.31 (18)
C17—C16—C21—C22	−179.55 (11)	C34—C42—C43—C44	177.83 (11)
C1—C16—C21—C22	−2.38 (18)	C42—C43—C44—C45	−0.98 (19)
C20—C21—C22—C27	49.42 (15)	C43—C44—C45—C46	2.26 (19)
C16—C21—C22—C27	−129.82 (13)	C43—C44—C45—C48	−177.20 (12)
C20—C21—C22—C23	−123.91 (13)	C44—C45—C46—C47	−1.28 (19)
C16—C21—C22—C23	56.84 (18)	C48—C45—C46—C47	178.18 (12)
C27—C22—C23—C24	1.07 (19)	C43—C42—C47—C46	2.28 (18)
C21—C22—C23—C24	174.50 (11)	C34—C42—C47—C46	−176.86 (11)
C22—C23—C24—C25	−0.7 (2)	C45—C46—C47—C42	−1.0 (2)
C23—C24—C25—C26	−0.13 (19)	C3A—N1A—C1A—O1A	−0.9 (3)
C23—C24—C25—C28	172.98 (12)	C2A—N1A—C1A—O1A	179.13 (19)
C24—C25—C26—C27	0.49 (18)	C3AA—N1AA—C1AA—O1AA	−179.6 (5)
C28—C25—C26—C27	−172.19 (11)	C2AA—N1AA—C1AA—O1AA	3.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1A^i	0.84	2.07	2.898 (2)	172
O2—H2···O1A^ii	0.84	1.99	2.753 (2)	160
C7—H7···O1	0.95	2.41	2.748 (2)	100
C14—H14···O1	0.95	2.39	2.743 (1)	102
C23—H23···O1	0.95	2.31	2.992 (2)	128
C26—H26···O2	0.95	2.30	2.953 (2)	125
C47—H47···O2	0.95	2.43	2.763 (2)	100

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

(IIIB) 2,2''-Bis[hydroxybis(4-methylphenyl)methyl]-1,1':4',1''-terphenyl acetonitrile monosolvate

Crystal data

C48H42O2·C2H3N	Z = 2
Mr = 691.87	F(000) = 736
Triclinic, P1	Dx = 1.199 Mg m^−3
a = 7.9452 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.2079 (4) Å	Cell parameters from 4522 reflections
c = 17.8589 (5) Å	θ = 2.3–25.2°
α = 83.687 (2)°	µ = 0.07 mm^−1
β = 78.583 (2)°	T = 100 K
γ = 76.417 (2)°	Irregular, colourless
V = 1916.57 (9) Å^3	0.17 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	Rint = 0.053
φ and ω scans	θmax = 27.8°, θmin = 2.7°
33150 measured reflections	h = −10→10
8974 independent reflections	k = −18→18
5876 reflections with I > 2σ(I)	l = −23→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0728P)^2 + 0.6918P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
8974 reflections	Δρmax = 0.30 e Å^−3
485 parameters	Δρmin = −0.50 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.71175 (17)	0.33833 (11)	0.19417 (8)	0.0211 (3)
H1	0.6860	0.3267	0.2417	0.032*
O2	0.70777 (17)	0.31003 (10)	0.58877 (8)	0.0190 (3)
H2	0.7375	0.2992	0.5422	0.028*
C1	0.8873 (2)	0.28570 (15)	0.16675 (11)	0.0163 (4)
C2	0.9107 (2)	0.30801 (15)	0.07998 (11)	0.0168 (4)
C3	0.8449 (3)	0.40141 (15)	0.05079 (12)	0.0217 (5)
H3	0.7773	0.4488	0.0848	0.026*
C4	0.8761 (3)	0.42643 (16)	−0.02694 (12)	0.0228 (5)
H4	0.8291	0.4906	−0.0454	0.027*
C5	0.9749 (3)	0.35941 (15)	−0.07857 (11)	0.0207 (4)
C6	1.0381 (3)	0.26617 (16)	−0.04968 (12)	0.0242 (5)
H6	1.1046	0.2187	−0.0839	0.029*
C7	1.0065 (3)	0.24042 (16)	0.02847 (12)	0.0223 (5)
H7	1.0510	0.1758	0.0467	0.027*
C8	1.0150 (3)	0.38747 (17)	−0.16289 (12)	0.0268 (5)
H8A	1.1422	0.3693	−0.1811	0.040*
H8B	0.9740	0.4577	−0.1718	0.040*
H8C	0.9547	0.3536	−0.1907	0.040*
C9	0.9032 (3)	0.17723 (15)	0.18771 (11)	0.0183 (4)
C10	1.0628 (3)	0.11640 (16)	0.19835 (12)	0.0238 (5)
H10	1.1631	0.1432	0.1952	0.029*
C11	1.0775 (3)	0.01699 (16)	0.21347 (13)	0.0269 (5)
H11	1.1882	−0.0232	0.2198	0.032*
C12	0.9335 (3)	−0.02468 (17)	0.21943 (12)	0.0280 (5)
C13	0.7748 (3)	0.03660 (18)	0.20943 (14)	0.0357 (6)
H13	0.6740	0.0100	0.2137	0.043*
C14	0.7592 (3)	0.13572 (17)	0.19337 (13)	0.0296 (5)
H14	0.6488	0.1756	0.1862	0.036*
C15	0.9525 (4)	−0.13255 (18)	0.23589 (16)	0.0432 (7)
H15A	0.9483	−0.1486	0.2909	0.065*
H15B	1.0653	−0.1665	0.2077	0.065*
H15C	0.8562	−0.1528	0.2197	0.065*
C16	1.0228 (2)	0.32355 (14)	0.19916 (11)	0.0156 (4)
C17	1.1842 (3)	0.32926 (15)	0.15301 (11)	0.0184 (4)
H17	1.2070	0.3102	0.1020	0.022*
C18	1.3124 (3)	0.36167 (15)	0.17893 (12)	0.0210 (4)
H18	1.4225	0.3626	0.1466	0.025*
C19	1.2793 (3)	0.39268 (16)	0.25213 (12)	0.0229 (5)
H19	1.3650	0.4164	0.2703	0.028*
C20	1.1196 (3)	0.38859 (15)	0.29847 (12)	0.0211 (4)
H20	1.0957	0.4115	0.3483	0.025*
C21	0.9921 (2)	0.35181 (14)	0.27451 (11)	0.0159 (4)
C22	0.8310 (2)	0.34660 (14)	0.33334 (10)	0.0158 (4)
C23	0.7958 (3)	0.25799 (15)	0.36702 (11)	0.0176 (4)
H23	0.8685	0.1989	0.3487	0.021*
C24	0.6551 (3)	0.25562 (15)	0.42712 (11)	0.0170 (4)
H24	0.6340	0.1948	0.4498	0.020*
C25	0.5447 (2)	0.34109 (14)	0.45455 (10)	0.0158 (4)
C26	0.5767 (3)	0.42936 (15)	0.41825 (11)	0.0177 (4)
H26	0.4995	0.4885	0.4340	0.021*
C27	0.7191 (3)	0.43162 (15)	0.35967 (11)	0.0185 (4)
H27	0.7405	0.4924	0.3371	0.022*
C28	0.3900 (2)	0.34233 (13)	0.51816 (11)	0.0151 (4)
C29	0.2260 (3)	0.38385 (15)	0.49808 (11)	0.0189 (4)
H29	0.2213	0.4112	0.4473	0.023*
C30	0.0698 (3)	0.38654 (15)	0.54961 (12)	0.0200 (4)
H30	−0.0402	0.4130	0.5340	0.024*
C31	0.0772 (3)	0.35011 (14)	0.62397 (12)	0.0188 (4)
H31	−0.0282	0.3504	0.6601	0.023*
C32	0.2388 (2)	0.31317 (14)	0.64572 (11)	0.0170 (4)
H32	0.2420	0.2908	0.6977	0.020*
C33	0.3972 (2)	0.30750 (14)	0.59449 (11)	0.0146 (4)
C34	0.5708 (2)	0.26028 (14)	0.62346 (11)	0.0151 (4)
C35	0.6260 (2)	0.15250 (14)	0.60737 (10)	0.0164 (4)
C36	0.8021 (3)	0.10472 (16)	0.59935 (12)	0.0243 (5)
H36	0.8883	0.1397	0.6026	0.029*
C37	0.8534 (3)	0.00692 (17)	0.58670 (14)	0.0299 (5)
H37	0.9747	−0.0239	0.5810	0.036*
C38	0.7319 (3)	−0.04719 (16)	0.58211 (13)	0.0293 (5)
C39	0.5565 (3)	0.00038 (16)	0.59112 (13)	0.0287 (5)
H39	0.4702	−0.0351	0.5889	0.034*
C40	0.5038 (3)	0.09853 (15)	0.60326 (12)	0.0229 (5)
H40	0.3826	0.1292	0.6088	0.027*
C41	0.7869 (4)	−0.15378 (18)	0.56756 (18)	0.0448 (7)
H41A	0.9107	−0.1691	0.5427	0.067*
H41B	0.7138	−0.1689	0.5343	0.067*
H41C	0.7719	−0.1925	0.6163	0.067*
C42	0.5526 (2)	0.27260 (15)	0.70944 (11)	0.0161 (4)
C43	0.5231 (3)	0.19930 (15)	0.76534 (11)	0.0192 (4)
H43	0.5166	0.1382	0.7506	0.023*
C44	0.5029 (3)	0.21411 (16)	0.84252 (12)	0.0237 (5)
H44	0.4822	0.1629	0.8796	0.028*
C45	0.5124 (3)	0.30160 (17)	0.86657 (12)	0.0238 (5)
C46	0.5433 (3)	0.37472 (16)	0.81035 (12)	0.0244 (5)
H46	0.5512	0.4355	0.8251	0.029*
C47	0.5629 (3)	0.36048 (15)	0.73322 (12)	0.0200 (4)
H47	0.5837	0.4117	0.6961	0.024*
C48	0.4890 (3)	0.3182 (2)	0.95038 (13)	0.0362 (6)
H48A	0.4388	0.2667	0.9813	0.054*
H48B	0.4095	0.3812	0.9609	0.054*
H48C	0.6035	0.3175	0.9634	0.054*
N1A	0.4545 (5)	0.0750 (3)	0.0798 (2)	0.1028 (13)
C1A	0.5932 (5)	0.0660 (3)	0.0446 (2)	0.0656 (10)
C2A	0.7675 (4)	0.0545 (3)	−0.0005 (2)	0.0798 (12)
H2A1	0.7774	0.0146	−0.0432	0.120*
H2A2	0.8542	0.0227	0.0316	0.120*
H2A3	0.7894	0.1184	−0.0205	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0152 (7)	0.0307 (9)	0.0155 (7)	−0.0034 (6)	0.0004 (5)	−0.0030 (6)
O2	0.0178 (7)	0.0250 (8)	0.0156 (7)	−0.0100 (6)	−0.0005 (6)	−0.0010 (6)
C1	0.0125 (9)	0.0206 (11)	0.0154 (10)	−0.0032 (8)	−0.0007 (7)	−0.0039 (8)
C2	0.0153 (9)	0.0207 (11)	0.0161 (9)	−0.0062 (8)	−0.0036 (8)	−0.0020 (8)
C3	0.0226 (11)	0.0205 (11)	0.0203 (10)	−0.0020 (8)	−0.0013 (8)	−0.0040 (8)
C4	0.0279 (11)	0.0192 (11)	0.0202 (10)	−0.0022 (9)	−0.0057 (9)	−0.0007 (8)
C5	0.0209 (10)	0.0244 (12)	0.0176 (10)	−0.0068 (9)	−0.0038 (8)	−0.0005 (8)
C6	0.0307 (12)	0.0224 (12)	0.0172 (10)	−0.0027 (9)	−0.0012 (9)	−0.0045 (9)
C7	0.0266 (11)	0.0181 (11)	0.0206 (11)	−0.0021 (9)	−0.0038 (9)	−0.0013 (8)
C8	0.0323 (12)	0.0300 (13)	0.0151 (10)	−0.0030 (10)	−0.0026 (9)	0.0005 (9)
C9	0.0232 (10)	0.0230 (11)	0.0104 (9)	−0.0099 (9)	−0.0011 (8)	−0.0011 (8)
C10	0.0242 (11)	0.0214 (12)	0.0260 (11)	−0.0075 (9)	−0.0014 (9)	−0.0017 (9)
C11	0.0295 (12)	0.0220 (12)	0.0275 (12)	−0.0044 (9)	−0.0041 (9)	0.0019 (9)
C12	0.0424 (14)	0.0248 (12)	0.0200 (11)	−0.0147 (10)	−0.0066 (10)	0.0029 (9)
C13	0.0398 (14)	0.0352 (15)	0.0404 (15)	−0.0238 (12)	−0.0154 (11)	0.0112 (11)
C14	0.0293 (12)	0.0306 (13)	0.0326 (13)	−0.0145 (10)	−0.0099 (10)	0.0072 (10)
C15	0.0635 (18)	0.0272 (14)	0.0462 (16)	−0.0227 (13)	−0.0176 (14)	0.0091 (12)
C16	0.0163 (9)	0.0139 (10)	0.0163 (10)	−0.0028 (8)	−0.0039 (8)	0.0002 (8)
C17	0.0183 (10)	0.0203 (11)	0.0160 (10)	−0.0033 (8)	−0.0024 (8)	−0.0020 (8)
C18	0.0161 (10)	0.0216 (11)	0.0244 (11)	−0.0051 (8)	−0.0027 (8)	0.0028 (9)
C19	0.0215 (11)	0.0237 (12)	0.0276 (11)	−0.0093 (9)	−0.0090 (9)	−0.0012 (9)
C20	0.0262 (11)	0.0235 (12)	0.0163 (10)	−0.0082 (9)	−0.0064 (8)	−0.0015 (8)
C21	0.0185 (10)	0.0126 (10)	0.0156 (9)	−0.0026 (8)	−0.0030 (8)	0.0017 (7)
C22	0.0195 (10)	0.0195 (10)	0.0101 (9)	−0.0058 (8)	−0.0047 (7)	−0.0010 (7)
C23	0.0218 (10)	0.0151 (10)	0.0148 (9)	−0.0011 (8)	−0.0030 (8)	−0.0030 (8)
C24	0.0210 (10)	0.0154 (10)	0.0153 (9)	−0.0055 (8)	−0.0036 (8)	0.0003 (8)
C25	0.0180 (10)	0.0195 (11)	0.0112 (9)	−0.0053 (8)	−0.0039 (7)	−0.0009 (7)
C26	0.0218 (10)	0.0160 (10)	0.0142 (9)	−0.0022 (8)	−0.0020 (8)	−0.0025 (8)
C27	0.0251 (10)	0.0165 (10)	0.0152 (10)	−0.0074 (8)	−0.0032 (8)	−0.0001 (8)
C28	0.0186 (10)	0.0109 (10)	0.0155 (9)	−0.0029 (8)	−0.0018 (8)	−0.0033 (7)
C29	0.0230 (10)	0.0177 (11)	0.0167 (10)	−0.0048 (8)	−0.0056 (8)	0.0008 (8)
C30	0.0184 (10)	0.0172 (11)	0.0250 (11)	−0.0024 (8)	−0.0078 (8)	−0.0001 (8)
C31	0.0170 (10)	0.0167 (11)	0.0216 (10)	−0.0042 (8)	0.0001 (8)	−0.0017 (8)
C32	0.0199 (10)	0.0150 (10)	0.0162 (10)	−0.0056 (8)	−0.0026 (8)	0.0012 (8)
C33	0.0189 (10)	0.0106 (9)	0.0151 (9)	−0.0047 (7)	−0.0030 (8)	−0.0009 (7)
C34	0.0143 (9)	0.0172 (10)	0.0141 (9)	−0.0058 (8)	−0.0005 (7)	−0.0003 (8)
C35	0.0201 (10)	0.0169 (10)	0.0110 (9)	−0.0024 (8)	−0.0025 (8)	0.0007 (7)
C36	0.0230 (11)	0.0245 (12)	0.0252 (11)	−0.0024 (9)	−0.0059 (9)	−0.0033 (9)
C37	0.0247 (12)	0.0272 (13)	0.0349 (13)	0.0061 (9)	−0.0103 (10)	−0.0064 (10)
C38	0.0348 (13)	0.0192 (12)	0.0327 (13)	0.0043 (10)	−0.0138 (10)	−0.0040 (9)
C39	0.0336 (13)	0.0200 (12)	0.0361 (13)	−0.0066 (10)	−0.0126 (10)	−0.0035 (10)
C40	0.0209 (10)	0.0186 (11)	0.0282 (11)	−0.0023 (8)	−0.0045 (9)	−0.0016 (9)
C41	0.0477 (16)	0.0231 (14)	0.0638 (19)	0.0061 (12)	−0.0229 (14)	−0.0107 (13)
C42	0.0130 (9)	0.0198 (11)	0.0150 (9)	−0.0027 (8)	−0.0028 (7)	−0.0003 (8)
C43	0.0217 (10)	0.0187 (11)	0.0176 (10)	−0.0048 (8)	−0.0040 (8)	−0.0017 (8)
C44	0.0248 (11)	0.0265 (12)	0.0187 (11)	−0.0066 (9)	−0.0029 (9)	0.0039 (9)
C45	0.0223 (11)	0.0326 (13)	0.0164 (10)	−0.0054 (9)	−0.0021 (8)	−0.0043 (9)
C46	0.0290 (11)	0.0245 (12)	0.0218 (11)	−0.0089 (9)	−0.0042 (9)	−0.0042 (9)
C47	0.0240 (11)	0.0175 (11)	0.0199 (10)	−0.0075 (8)	−0.0043 (8)	−0.0005 (8)
C48	0.0453 (15)	0.0483 (16)	0.0173 (11)	−0.0164 (12)	−0.0021 (10)	−0.0047 (11)
N1A	0.072 (2)	0.147 (4)	0.101 (3)	−0.047 (2)	0.010 (2)	−0.055 (3)
C1A	0.051 (2)	0.077 (3)	0.073 (2)	−0.0204 (18)	−0.0040 (18)	−0.023 (2)
C2A	0.056 (2)	0.087 (3)	0.100 (3)	−0.021 (2)	−0.007 (2)	−0.023 (2)

Geometric parameters (Å, º)

O1—C1	1.437 (2)	C25—C26	1.401 (3)
O1—H1	0.8400	C25—C28	1.498 (3)
O2—C34	1.437 (2)	C26—C27	1.384 (3)
O2—H2	0.8400	C26—H26	0.9500
C1—C9	1.527 (3)	C27—H27	0.9500
C1—C2	1.530 (3)	C28—C29	1.397 (3)
C1—C16	1.540 (3)	C28—C33	1.405 (3)
C2—C7	1.386 (3)	C29—C30	1.386 (3)
C2—C3	1.392 (3)	C29—H29	0.9500
C3—C4	1.382 (3)	C30—C31	1.378 (3)
C3—H3	0.9500	C30—H30	0.9500
C4—C5	1.389 (3)	C31—C32	1.383 (3)
C4—H4	0.9500	C31—H31	0.9500
C5—C6	1.383 (3)	C32—C33	1.393 (3)
C5—C8	1.505 (3)	C32—H32	0.9500
C6—C7	1.392 (3)	C33—C34	1.546 (3)
C6—H6	0.9500	C34—C35	1.533 (3)
C7—H7	0.9500	C34—C42	1.539 (3)
C8—H8A	0.9800	C35—C40	1.388 (3)
C8—H8B	0.9800	C35—C36	1.391 (3)
C8—H8C	0.9800	C36—C37	1.384 (3)
C9—C14	1.388 (3)	C36—H36	0.9500
C9—C10	1.391 (3)	C37—C38	1.387 (3)
C10—C11	1.390 (3)	C37—H37	0.9500
C10—H10	0.9500	C38—C39	1.385 (3)
C11—C12	1.388 (3)	C38—C41	1.511 (3)
C11—H11	0.9500	C39—C40	1.387 (3)
C12—C13	1.385 (3)	C39—H39	0.9500
C12—C15	1.506 (3)	C40—H40	0.9500
C13—C14	1.387 (3)	C41—H41A	0.9800
C13—H13	0.9500	C41—H41B	0.9800
C14—H14	0.9500	C41—H41C	0.9800
C15—H15A	0.9800	C42—C47	1.387 (3)
C15—H15B	0.9800	C42—C43	1.389 (3)
C15—H15C	0.9800	C43—C44	1.389 (3)
C16—C17	1.395 (3)	C43—H43	0.9500
C16—C21	1.405 (3)	C44—C45	1.382 (3)
C17—C18	1.385 (3)	C44—H44	0.9500
C17—H17	0.9500	C45—C46	1.393 (3)
C18—C19	1.382 (3)	C45—C48	1.509 (3)
C18—H18	0.9500	C46—C47	1.387 (3)
C19—C20	1.380 (3)	C46—H46	0.9500
C19—H19	0.9500	C47—H47	0.9500
C20—C21	1.397 (3)	C48—H48A	0.9800
C20—H20	0.9500	C48—H48B	0.9800
C21—C22	1.498 (3)	C48—H48C	0.9800
C22—C27	1.388 (3)	N1A—C1A	1.142 (4)
C22—C23	1.399 (3)	C1A—C2A	1.440 (5)
C23—C24	1.392 (3)	C2A—H2A1	0.9800
C23—H23	0.9500	C2A—H2A2	0.9800
C24—C25	1.394 (3)	C2A—H2A3	0.9800
C24—H24	0.9500
C1—O1—H1	109.5	C27—C26—C25	120.91 (18)
C34—O2—H2	109.5	C27—C26—H26	119.5
O1—C1—C9	110.32 (15)	C25—C26—H26	119.5
O1—C1—C2	103.61 (15)	C26—C27—C22	121.11 (19)
C9—C1—C2	111.40 (16)	C26—C27—H27	119.4
O1—C1—C16	110.70 (15)	C22—C27—H27	119.4
C9—C1—C16	110.70 (16)	C29—C28—C33	118.73 (17)
C2—C1—C16	109.90 (15)	C29—C28—C25	115.37 (17)
C7—C2—C3	117.82 (19)	C33—C28—C25	125.89 (17)
C7—C2—C1	122.57 (18)	C30—C29—C28	122.29 (18)
C3—C2—C1	119.46 (17)	C30—C29—H29	118.9
C4—C3—C2	121.12 (19)	C28—C29—H29	118.9
C4—C3—H3	119.4	C31—C30—C29	118.74 (18)
C2—C3—H3	119.4	C31—C30—H30	120.6
C3—C4—C5	121.2 (2)	C29—C30—H30	120.6
C3—C4—H4	119.4	C30—C31—C32	119.66 (18)
C5—C4—H4	119.4	C30—C31—H31	120.2
C6—C5—C4	117.68 (19)	C32—C31—H31	120.2
C6—C5—C8	121.00 (19)	C31—C32—C33	122.57 (18)
C4—C5—C8	121.31 (19)	C31—C32—H32	118.7
C5—C6—C7	121.38 (19)	C33—C32—H32	118.7
C5—C6—H6	119.3	C32—C33—C28	117.89 (17)
C7—C6—H6	119.3	C32—C33—C34	118.68 (16)
C2—C7—C6	120.8 (2)	C28—C33—C34	123.40 (16)
C2—C7—H7	119.6	O2—C34—C35	110.70 (15)
C6—C7—H7	119.6	O2—C34—C42	103.29 (15)
C5—C8—H8A	109.5	C35—C34—C42	110.47 (16)
C5—C8—H8B	109.5	O2—C34—C33	110.87 (15)
H8A—C8—H8B	109.5	C35—C34—C33	110.21 (15)
C5—C8—H8C	109.5	C42—C34—C33	111.13 (15)
H8A—C8—H8C	109.5	C40—C35—C36	117.77 (19)
H8B—C8—H8C	109.5	C40—C35—C34	121.91 (17)
C14—C9—C10	117.9 (2)	C36—C35—C34	120.28 (18)
C14—C9—C1	120.49 (19)	C37—C36—C35	121.0 (2)
C10—C9—C1	121.50 (18)	C37—C36—H36	119.5
C11—C10—C9	120.9 (2)	C35—C36—H36	119.5
C11—C10—H10	119.6	C36—C37—C38	121.5 (2)
C9—C10—H10	119.6	C36—C37—H37	119.3
C12—C11—C10	121.3 (2)	C38—C37—H37	119.3
C12—C11—H11	119.4	C39—C38—C37	117.4 (2)
C10—C11—H11	119.4	C39—C38—C41	120.8 (2)
C13—C12—C11	117.4 (2)	C37—C38—C41	121.8 (2)
C13—C12—C15	122.2 (2)	C38—C39—C40	121.6 (2)
C11—C12—C15	120.4 (2)	C38—C39—H39	119.2
C12—C13—C14	121.8 (2)	C40—C39—H39	119.2
C12—C13—H13	119.1	C39—C40—C35	120.8 (2)
C14—C13—H13	119.1	C39—C40—H40	119.6
C13—C14—C9	120.7 (2)	C35—C40—H40	119.6
C13—C14—H14	119.7	C38—C41—H41A	109.5
C9—C14—H14	119.7	C38—C41—H41B	109.5
C12—C15—H15A	109.5	H41A—C41—H41B	109.5
C12—C15—H15B	109.5	C38—C41—H41C	109.5
H15A—C15—H15B	109.5	H41A—C41—H41C	109.5
C12—C15—H15C	109.5	H41B—C41—H41C	109.5
H15A—C15—H15C	109.5	C47—C42—C43	117.83 (18)
H15B—C15—H15C	109.5	C47—C42—C34	119.50 (17)
C17—C16—C21	117.86 (17)	C43—C42—C34	122.66 (18)
C17—C16—C1	119.50 (17)	C42—C43—C44	120.9 (2)
C21—C16—C1	122.64 (16)	C42—C43—H43	119.5
C18—C17—C16	122.35 (18)	C44—C43—H43	119.5
C18—C17—H17	118.8	C45—C44—C43	121.5 (2)
C16—C17—H17	118.8	C45—C44—H44	119.2
C19—C18—C17	119.60 (19)	C43—C44—H44	119.2
C19—C18—H18	120.2	C44—C45—C46	117.42 (19)
C17—C18—H18	120.2	C44—C45—C48	121.7 (2)
C20—C19—C18	118.95 (19)	C46—C45—C48	120.9 (2)
C20—C19—H19	120.5	C47—C46—C45	121.3 (2)
C18—C19—H19	120.5	C47—C46—H46	119.3
C19—C20—C21	122.19 (19)	C45—C46—H46	119.3
C19—C20—H20	118.9	C46—C47—C42	121.00 (19)
C21—C20—H20	118.9	C46—C47—H47	119.5
C20—C21—C16	118.93 (17)	C42—C47—H47	119.5
C20—C21—C22	115.53 (17)	C45—C48—H48A	109.5
C16—C21—C22	125.55 (17)	C45—C48—H48B	109.5
C27—C22—C23	118.39 (18)	H48A—C48—H48B	109.5
C27—C22—C21	119.61 (18)	C45—C48—H48C	109.5
C23—C22—C21	121.84 (17)	H48A—C48—H48C	109.5
C24—C23—C22	120.55 (18)	H48B—C48—H48C	109.5
C24—C23—H23	119.7	N1A—C1A—C2A	179.5 (4)
C22—C23—H23	119.7	C1A—C2A—H2A1	109.5
C23—C24—C25	121.02 (19)	C1A—C2A—H2A2	109.5
C23—C24—H24	119.5	H2A1—C2A—H2A2	109.5
C25—C24—H24	119.5	C1A—C2A—H2A3	109.5
C24—C25—C26	117.93 (17)	H2A1—C2A—H2A3	109.5
C24—C25—C28	123.01 (18)	H2A2—C2A—H2A3	109.5
C26—C25—C28	118.99 (17)
O1—C1—C2—C7	−144.55 (19)	C24—C25—C26—C27	−3.4 (3)
C9—C1—C2—C7	−26.0 (3)	C28—C25—C26—C27	179.42 (18)
C16—C1—C2—C7	97.1 (2)	C25—C26—C27—C22	2.2 (3)
O1—C1—C2—C3	40.1 (2)	C23—C22—C27—C26	0.5 (3)
C9—C1—C2—C3	158.74 (18)	C21—C22—C27—C26	−174.89 (18)
C16—C1—C2—C3	−78.2 (2)	C24—C25—C28—C29	−116.4 (2)
C7—C2—C3—C4	−1.0 (3)	C26—C25—C28—C29	60.7 (2)
C1—C2—C3—C4	174.57 (18)	C24—C25—C28—C33	64.8 (3)
C2—C3—C4—C5	−0.3 (3)	C26—C25—C28—C33	−118.2 (2)
C3—C4—C5—C6	1.2 (3)	C33—C28—C29—C30	−4.0 (3)
C3—C4—C5—C8	−177.6 (2)	C25—C28—C29—C30	177.07 (19)
C4—C5—C6—C7	−1.0 (3)	C28—C29—C30—C31	2.4 (3)
C8—C5—C6—C7	177.9 (2)	C29—C30—C31—C32	0.9 (3)
C3—C2—C7—C6	1.2 (3)	C30—C31—C32—C33	−2.6 (3)
C1—C2—C7—C6	−174.14 (19)	C31—C32—C33—C28	0.9 (3)
C5—C6—C7—C2	−0.3 (3)	C31—C32—C33—C34	−176.97 (18)
O1—C1—C9—C14	30.7 (2)	C29—C28—C33—C32	2.3 (3)
C2—C1—C9—C14	−83.8 (2)	C25—C28—C33—C32	−178.93 (18)
C16—C1—C9—C14	153.58 (18)	C29—C28—C33—C34	−179.94 (17)
O1—C1—C9—C10	−152.19 (18)	C25—C28—C33—C34	−1.1 (3)
C2—C1—C9—C10	93.3 (2)	C32—C33—C34—O2	−142.87 (17)
C16—C1—C9—C10	−29.3 (2)	C28—C33—C34—O2	39.4 (2)
C14—C9—C10—C11	0.6 (3)	C32—C33—C34—C35	94.2 (2)
C1—C9—C10—C11	−176.60 (19)	C28—C33—C34—C35	−83.6 (2)
C9—C10—C11—C12	−0.8 (3)	C32—C33—C34—C42	−28.6 (2)
C10—C11—C12—C13	0.2 (3)	C28—C33—C34—C42	153.63 (18)
C10—C11—C12—C15	−180.0 (2)	O2—C34—C35—C40	−151.18 (18)
C11—C12—C13—C14	0.6 (4)	C42—C34—C35—C40	95.0 (2)
C15—C12—C13—C14	−179.2 (2)	C33—C34—C35—C40	−28.2 (2)
C12—C13—C14—C9	−0.8 (4)	O2—C34—C35—C36	31.4 (2)
C10—C9—C14—C13	0.2 (3)	C42—C34—C35—C36	−82.4 (2)
C1—C9—C14—C13	177.4 (2)	C33—C34—C35—C36	154.39 (18)
O1—C1—C16—C17	−142.55 (18)	C40—C35—C36—C37	0.8 (3)
C9—C1—C16—C17	94.8 (2)	C34—C35—C36—C37	178.39 (19)
C2—C1—C16—C17	−28.7 (2)	C35—C36—C37—C38	−0.5 (3)
O1—C1—C16—C21	38.4 (2)	C36—C37—C38—C39	−0.4 (4)
C9—C1—C16—C21	−84.3 (2)	C36—C37—C38—C41	179.4 (2)
C2—C1—C16—C21	152.21 (18)	C37—C38—C39—C40	0.8 (4)
C21—C16—C17—C18	−0.2 (3)	C41—C38—C39—C40	−178.9 (2)
C1—C16—C17—C18	−179.31 (19)	C38—C39—C40—C35	−0.5 (3)
C16—C17—C18—C19	−2.1 (3)	C36—C35—C40—C39	−0.4 (3)
C17—C18—C19—C20	1.4 (3)	C34—C35—C40—C39	−177.88 (19)
C18—C19—C20—C21	1.7 (3)	O2—C34—C42—C47	39.8 (2)
C19—C20—C21—C16	−4.0 (3)	C35—C34—C42—C47	158.26 (17)
C19—C20—C21—C22	176.27 (19)	C33—C34—C42—C47	−79.1 (2)
C17—C16—C21—C20	3.1 (3)	O2—C34—C42—C43	−141.19 (18)
C1—C16—C21—C20	−177.75 (18)	C35—C34—C42—C43	−22.8 (2)
C17—C16—C21—C22	−177.13 (18)	C33—C34—C42—C43	99.9 (2)
C1—C16—C21—C22	2.0 (3)	C47—C42—C43—C44	0.6 (3)
C20—C21—C22—C27	65.7 (2)	C34—C42—C43—C44	−178.36 (18)
C16—C21—C22—C27	−114.0 (2)	C42—C43—C44—C45	−0.4 (3)
C20—C21—C22—C23	−109.5 (2)	C43—C44—C45—C46	−0.1 (3)
C16—C21—C22—C23	70.7 (3)	C43—C44—C45—C48	179.5 (2)
C27—C22—C23—C24	−2.0 (3)	C44—C45—C46—C47	0.4 (3)
C21—C22—C23—C24	173.26 (18)	C48—C45—C46—C47	−179.2 (2)
C22—C23—C24—C25	0.8 (3)	C45—C46—C47—C42	−0.1 (3)
C23—C24—C25—C26	1.9 (3)	C43—C42—C47—C46	−0.4 (3)
C23—C24—C25—C28	178.93 (18)	C34—C42—C47—C46	178.62 (18)

Hydrogen-bond geometry (Å, º)

Cg4 is the centroid of which? ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cg4	0.84	2.74	3.531 (8)	158
O2—H2···Cg4	0.84	2.76	3.502 (8)	149
C18—H18···O1^i	0.95	2.54	3.175 (3)	124
C2A—H2A1···N1A^ii	0.98	2.68	3.404 (5)	131

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